Affordable Stays Near Shady Lake, Annapolis

Flag House Inn
Hotel
24 Randall St, Annapolis, MD, 21401, USA

Flag House Inn is located in Annapolis, 1.1 miles from Annapolis Harbor and 30 miles from Carroll Park. With a shared lounge, the 5-star inn has air-conditioned rooms with free WiFi, each with a private bathroom. Private parking is available on site. At the inn, each room comes with a closet. At Flag House Inn every room is equipped with a seating area. Sports Legends Museum at Camden Yards is 30 miles from the accommodation, while Baltimore Convention Center is 30 miles away. The nearest airport is Baltimore - Washington International Airport, 21 miles from Flag House Inn.

Guest Reviews:

- "Absolutely Awesome!" - "Romantic getaway"

Flag House Inn
Bed & Breakfast
26 Randall St, Annapolis, MD, 21401, USA

Bed & breakfast with free breakfast, steps from U.S. Naval Academy
Valet parking, a refrigerator in a common area, and concierge services are available at this bed & breakfast. Free breakfast (local cuisine) and free WiFi in public areas are also provided. Additionally, self parking, free newspapers, and tour/ticket assistance are onsite.
Flag House Inn offers 5 accommodations with free minibar items and espresso makers. These individually decorated and furnished accommodations have separate sitting areas. Memory foam beds feature Frette Italian sheets and premium bedding. 55-inch LED televisions come with digital channels.

Bathrooms include showers, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include complimentary newspapers and complimentary bottled water. Hypo-allergenic bedding and irons/ironing boards can be requested. Housekeeping is provided daily.

Guest Reviews:

- "Very close to downtown!" - "Excellent staff. Excellent room. Excellent breakfast. Fantastic location! Spent some lovely time on the front porch. " - "Very nice facility. Close to shops and restaurants." - "Great place great people " - "Great place to stay when visiting Annapolis." - "Comfortable stay, high quality amazing service. Within walking distance to everything " - "Great location right across from the Naval Academy and restaurants in Annapolis. Friendly and attentive owners and staff. "

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Apartment
21 Randall Street B, Annapolis, MD, MD 21401

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity offers accommodations in Annapolis, 30 miles from Sports Legends Museum at Camden Yards and 30 miles from Baltimore Convention Center. The air-conditioned accommodation is 1.1 miles from Annapolis Harbor. Outdoor seating is also available at the apartment. With free Wifi, this 1-bedroom apartment offers a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the apartment. The accommodation is non-smoking. Inner Harbor is 30 miles from COZY DOWNTOWN APARTMENT-Naval Academy Vicinity, while Power Plant is 31 miles from the property. Baltimore - Washington International Airport is 21 miles away.

Guest Reviews:

- "Great Location"

Stunning Waterfront Cottage with Breathtaking Views!
House
Annapolis, Maryland, USA

A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in this upgraded cottage. This 2 BR, 1 BA house sleeps 4-6 people. Features include an open floor plan, with hardwood floors throughout, customized cabinetry, and granite counter tops. The modern kitchen offers all new appliances; stove, microwave, side by side refrigerator, coffee maker, dishwasher and is fully stocked with dishes, cookware and utensils. Everything to cook up a feast! The marble tiled bathroom features a large shower, vanity and the necessities of a home away from home! The living room is furnished with a comfy sleeper sofa, two plush chairs, and a large flat screen TV with cable. A bright and sun-filled room makes a perfect setting for morning coffee or a cozy dinner at the table, seating for four. Double French Doors off the living room open to a deck with a table and chairs overlooking Back Creek and the full back yard. Relax and sit on the deck with a cold drink and enjoy the waterfront views or take advantage of the kayaks provided for you.
The property is only minutes from Historic, Downtown Annapolis and has easy access to the Chesapeake Bay. Convenient shopping is within 2 miles; grocery, pharmacy, liquor stores, as well as some amazing restaurants.
Just footsteps away, The Cottage offers the amenities of the marina which include a pool (in season), Fitness Center, Wi-Fi, bikes, and a water taxi location.

Guest Reviews:

- "The cottage is beautiful and the view of the marina is even better. The swimming pool area has very comfortable lounge chairs and a lifeguard on duty. We had a wonderful stay and I couldn't recommend this location enough." - "We had the best time- such a special place. House has everything you need and the amenities of the marina are so fun!" - "I have stayed at this property every summer since 2017. It is in a great location and has many amenities available through the marina. Clean, updated and with boats at your doorstep. The property owner is very responsive and helpful."

Annapolis Vacation Home 2 Mi to Quiet Waters Park
House
Annapolis, MD, USA

Annapolis Vacation Home 2 Mi to Quiet Waters Park offers accommodations in Annapolis, 3.2 miles from Annapolis Harbor and 28 miles from Addison Road-Seat Pleasant. This vacation home is 31 miles from Sports Legends Museum at Camden Yards. Free Wifi is available throughout the property and Sparrows Beach is a 16-minute walk away. The air-conditioned vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 4 bathrooms with a bath and a hair dryer. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Baltimore - Washington International Airport is 22 miles from the property.

Guest Reviews:

- "A great place to stay for a family - on a quiet private street yet close to everything." - "Enjoyed this property very much. Perfect for our trip."

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
House
Annapolis, Maryland, USA

Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spacious fenced in back yard and is only steps away from the Naval Academy. The State House, great restaurants and fantastic shopping are also a close distance. Located on historic East Street, you will also find yourself surrounded by important landmarks, popular seasonal events and an all around perfectly positive Annapolis energy. Whether you're in town for an event, a football game or just having crabs with friends in the backyard; this house is the perfect quintessential Annapolis getaway. *Note: As of October 1st, 2024, we unfortunately can no longer offer a parking pass. There are several overnight parking garages guests can chose use in walking distance to our home. *

Guest Reviews:

- "We had a great stay in Annapolis. You could not beat the location of the house and the house itself was very comfortable and clean - perfect for our getaway when we had to come down for work and made it a little vacation too!" - "We came into town for the Naval Academy lacrosse camp! This was a perfect location- right across the street! The home was well stocked with everything we needed! We appreciated the use of the parking pass for the parking structure. We got our steps in—but it was nice because restaurants, shopping we in close proximity! Kara and Andy are wonderful hosts! We had a chance to get to know the neighbors who were extremely nice and helpful! Thanks again for a wonderful stay!"

Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!
Villa
1709 River Road, Annapolis, MD, MD 21409, USA

Providing a garden, Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! features accommodations in Annapolis. This beachfront property offers access to a balcony, free private parking, and free Wifi. On clear days, guests can head outside to enjoy the villa's outdoor fireplace or simply kick back and relax. Featuring a terrace and sea views, the villa includes 2 bedrooms, a living room, satellite flat-screen TV, an equipped kitchen, and 1 bathroom with a bath and a shower. Featuring air conditioning, this unit has a dressing room and a fireplace. This villa is allergy-free and non-smoking. During warmer months, you can make use of the barbecue facilities and eat on the private patio. Guests at the villa will be able to enjoy activities in and around Annapolis, like cycling, canoeing, and hiking. The villa has a picnic area where you can spend the day outdoors. Annapolis Harbor is 8.7 miles from Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!, while Sports Legends Museum at Camden Yards is 29 miles from the property. Baltimore - Washington International Airport is 20 miles away.

Guest Reviews:

- "Beautiful Chesapeake Bay for our family!" - "We had the best time! Will be back and hope to stay longer." - "Great scenic location- comfortable and clean" - "Very pleasant stay in a peaceful house." - "Everything as lovely" - "Beautiful waterfront property, very friendly and responsive host, a great place to stay with family"

Historic Downtown Charmer, Water Views and Parking!
House
Annapolis, Maryland, USA

Life is beautiful in historic downtown Annapolis, with great restaurants, shops and romantic waterfront at your doorstep. Live like a local in a home built in 1875 but updated for today's lifestyles. This two bedroom, 1 1/2 bath home with a designated, off-street parking space -- a rare perk in this National Landmark district -- makes it easy for guests to arrive, unpack and unplug.

Walk down Pinkney Street to experience the restaurants and shops of downtown and see the yachts along Ego Alley. Visit the United States Naval Academy just three blocks away. Or walk up the street on brick and cobblestone sidewalks to explore the grounds of the oldest state house in continued use in America or St. John's College, dating to the 17th century. Experience the restaurants, charming antique stores and neighborhoods around State and Church Circles and beyond.

This 1875 cedar shake home sits in a row of townhouses that have been updated for modern living, with hardwood floors and ceramic tile on the main floor and new carpeting in the bedrooms. Enjoy the cozy fireplace during the cold winter nights, or in the warm summer months, take your morning coffee or afternoon cocktails to the rooftop deck to enjoy views of the water, the boats and City Dock.

This well-decorated house features an open floor plan with updated, fully equipped kitchen, a living room with flat-screen TV and fireplace, dining room and half bath on the first level. There is a small deck facing the courtyard and parking with space to sit and enjoy the morning sun. On the second floor, the generously sized queen bedroom features a walk-in closet, private access to a shared bath and wall-mounted flat screen television. A well-appointed guest room provides two comfortable twin beds. But the second floor also contains a hidden surprise -- a skylit ship's ladder to a widow's walk and rooftop deck with beautiful views of Ego Alley and Spa Creek.

As with any luxury property, the essentials -- linens, WiFi, coffee, and toiletries -- are included.

Historic Annapolis is the place to be during Naval Academy events and football games, St. John's College visits and graduation, boat shows and more. It is the perfect destination for a romantic weekend, a girls' getaway, family reunions, temporary military assignment and more. Consider making this cozy retreat on a historic street your home away from home when you come to visit Maryland's state capital.

Guest Reviews:

- "Stayed here for USNA plebe parent's weekend. What an amazing weekend and your place made it that much more special. We will be back again soon." - "Comfortable and very well maintained townhouse with off-street parking in downtown Annapolis. Walking distance to Naval Academy, Annapolis Harbor, Church and State Circles, and Market Street. Outstanding choice of restaurants. Ideal summer getaway." - "Great row house on a quiet historic street minutes from City Dock. Easy walking everywhere."

Waterfront Annapolis Home Fire Pit and Fishing Pier
House
Annapolis, MD, USA

Waterfront Annapolis Home Fire Pit and Fishing Pier is located in Annapolis, just 8.7 miles from Annapolis Harbor and 29 miles from Sports Legends Museum at Camden Yards. Free Wifi is featured throughout the property and private parking is available on site. Baltimore Convention Center is 29 miles away and Korean War Memorial is 29 miles from the vacation home. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with free toiletries. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Inner Harbor is 29 miles from Waterfront Annapolis Home Fire Pit and Fishing Pier, while Power Plant is 29 miles away. Baltimore - Washington International Airport is 20 miles from the property.

Guest Reviews:

- "Relaxing get away. Nice way to connect with nature." - "Wonderful location. Great outdoor space."

Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
Apartment
Annapolis, Maryland, USA

A beautiful basement apartment in the city of Annapolis, in the quiet Eastport neighborhood, a walk to marinas, historic DT Annapolis, and US Naval Academy. Sleeps four, plus two large couches in the living room. A full bath, kitchenette, and a study area. An open living design, great for a short stay. HD TV, Network & Smart TV, and high-speed Internet/WiFi service provided. No pets allowed—free parking- street.

Guest Reviews:

- "Super easy check in process and check out. The vrbo was exactly as advertised and was perfect." - "Great for two people, with space to sleep in 2 different rooms if desired. Hosts were helpful and flexible. We loved the food, craft beer, and atmosphere at Forward Brewery nearby. And we really enjoyed Quiet Waters Park, with hiking trails and picnic areas. The park also had playgrounds and outdoor ice skating for families." - "Clean spacious apartment. Good air conditioner and comfortable bed."

Stylish + fresh bungalow 2 blocks from N-MC Stadium
House
Poplar Avenue 912, Annapolis, MD, 21401, USA

Stylish + fresh bungalow 2 blocks from N-MC Stadium offers accommodations in Annapolis, 2.7 miles from Annapolis Harbor and 28 miles from Sports Legends Museum at Camden Yards. Both free Wifi and parking on-site are available at the vacation home free of charge. Power Plant is 29 miles from the vacation home and Pier Six Concert Pavilion is 29 miles away. The air-conditioned vacation home is composed of 2 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. A TV is provided. For added privacy, the accommodation features a private entrance. Guests can also relax in the garden. Baltimore Convention Center is 28 miles from Stylish + fresh bungalow 2 blocks from N-MC Stadium, while Inner Harbor is 29 miles away. Baltimore - Washington International Airport is 19 miles from the property.

Guest Reviews:

- "Super charming little house in quiet area" - "The perfect place in Annapolis this house is a treasure" - "Great price and location!! Staff were helpful and quick to respond." - "Lovely property, great location." - "We enjoyed our stay tremendously. We are originally from Annapolis, MD so it was fun to catch up with friends and see al"

Craftsman Bungalow Suite Near Naval Academy Stadium and Historic District
Apartment
Annapolis, Maryland, USA

This 1920's Craftsman style bungalow is 1/2 block from the Naval Academy Stadium and within walking distance of the Historic District. Its close proximity to Baltimore, Washington DC and Maryland's Eastern Shore make it a great location for day tripping. This well appointed bright lower level suite with private entrance includes many Craftsman details including a custom quarter sawn oak wine bar and kitchen cabinets. The open floor plan includes a living room and wine bar with fridge/freezer, sink and Advantium Microwave and Ice Stone counter tops. The suite offers a bedroom with a full sized bed, full bath with tub/shower and laundry with washer/dryer. Guests are welcome to share the patio and backyard with the main house. Friendly pugs may occasionally greet guests in the backyard.

Guest Reviews:

- "Ideal location to USNA. Walked a block to stadium and shuttle to academy. Very quiet, homey space with kitchenette. Hosts very accommodating." - "Beautiful home very clean beautiful neighborhood lovely neighbors! Communication was quick! Just a little to far from park, but overall beautiful home nice stay! Ty we was very comfortable!" - "This rental was super clean and conveniently located to all things Annapolis. Hosts were prompt with answering a quick question for us and we had a great stay."

King George Downtown Annapolis Getaway
Apartment
165 King George Street, Annapolis, MD, MD 21401

King George Downtown Annapolis Getaway offers accommodations in Annapolis, 1.4 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards. This apartment offers air-conditioned accommodations with a patio. Baltimore Convention Center is 30 miles from the apartment and Inner Harbor is 31 miles away. With free Wifi, this 2-bedroom apartment provides a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are provided in the apartment. For added privacy, the accommodation features a private entrance. Guests can make the most of the warm weather with the property's barbecue facilities. Power Plant is 31 miles from the apartment. Baltimore - Washington International Airport is 21 miles away.

Guest Reviews:

- "A Royal Retreat" - "loved annapolis and seeing our friends but won’t stay here again" - "lovely, well appointed apartment in the perfect location." - "Great place to spend a weekend in Annapolis."

Waterfront Oasis of Annapolis Star
Apartment
Annapolis, Maryland, USA

Studio, furnished apartment above detached garage on family's sprawling property. Queen-bed, with pull out full couch. Sleeps up to 4. Well-appointed and outfitted, eat-in kitchenette. Gorgeous bathroom. Vaulted ceilings. Access to our saltwater pool(seasonal) that is shared with your host family and other Oasis guests, outdoor fireplace with TV(also shared with other Oasis guests), outdoor grill and pavilion with TV and Bose system.Less than a 10 min drive to downtown Annapolis.

Keep reading... if you want to know more about this amazing property

The property is equipped with everything you will need for your stay including a full-size fridge, Keurig coffee maker, teapot, stove and dishwasher. Just outside the property entrance is the gorgeous “Oasis” pool.
This studio is PERFECT for small families or friends visiting the United States Naval Academy, Annapolis Boat Shows or any of the many Annapolis events we have going on here year-round.

The property is a mere 3.5 miles away from Downtown Annapolis.

Covid-19 precautions-Our guests are our priority. We take every precaution when cleaning the property and make sure we meet every industry standard. We go above and beyond to ensure all surfaces and high touch areas are cleaned thoroughly and disinfected.
**No-contact check-in available upon request**

SLEEPING ARRANGEMENTS
STUDIO/1BR/1BA
Queen size bed
Pull-out couch
FEATURES
Heated, Saltwater pool(shared)
Covered Pavilion with ample seating and outdoor TV
Outdoor fireplace-firewood provided
Outdoor grill/BBQ(propane)
Full kitchen/kitchen table with seating
Free Wi-Fi
Luxury Linens & towels
Complimentary sodas/water/coffee/tea
Complimentary toiletries
Ample parking on site
Perfect place to relax, reconnect and see the sites of Annapolis
Please note-no washer/dryer or oven on site
No smoking in this property
No pets allowed
There is video surveillance on the outside peripheral aspect of the entryway of the property this is for security purposes only.

AMENITIES
Too many to list! We provide at all. Just ask
Soaps, conditioners, lotions, paper towels, sodas, water, dish soap, scrubbers, wine/champagne($), even a boat ride with a licensed boat captain($)
Captain Andy can show you all Annapolis has to offer AND can even give you a lesson on how to wakeboard/Waterski- inquire before or after you book.

Your comfortable bed, including the sofa bed, are made for you with freshly laundered sheets and you have bath as well as pool towels.

HOUSE RULES
No smoking. No pets. No parties/events please.
Check in time 3:00 p.m.
Check out time 11:00 a.m.

All guests have access to the fabulous and GRAND prize winning (2022 LCA GRAND PRIZE-OUTDOOR LIVING AREA-McHale Landscape Design, Inc.) Oasis Pool and outdoor living spaces.

Guest Reviews:

- "This is a beautiful property and the Hostess, Beth, was very accommodating. We stayed in the Star, above the garage. It was perfectly clean and comfortable. We would definitely come back in the future." - "Although our stay at Waterfront Oasis of Annapolis Star was brief, it was a great experience. The location was perfect! Beth and Andy were incredible host and welcomed us into the home as if we were family! We are looking forward to making a return trip when we are able to spend a bit more time! "

Vintage Charm: Annapolis Retreat
House
3 Hill Street, Annapolis, MD, MD 21401, USA

Offering a garden, Vintage Charm: Annapolis Retreat offers accommodations in Annapolis. The vacation home, set in a building dating from 1909, features free Wifi and free private parking. Baltimore Convention Center is 29 miles from the vacation home and Inner Harbor is 29 miles away. Providing access to a patio with quiet street views, the spacious air-conditioned vacation home consists of 3 bedrooms. Featuring a terrace with garden views, this vacation home also comes with a flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a bath and a hair dryer. The property has an outdoor dining area. Annapolis Harbor is 1.9 miles from the vacation home, while Sports Legends Museum at Camden Yards is 29 miles from the property. Baltimore - Washington International Airport is 20 miles away.

Guest Reviews:

- "This home is beautiful and exactly what we needed for a weekend away with our daughter. Downtown was walkable, and this" - "Host was friendly and attentive. Loved being close to restaurants and coffee shops. Very easy stroll to Main Street. Wou" - "An extremely charming home in an excellent location."

Charming cottage with parking. Easy walk to downtown.
House
Annapolis, Maryland, USA

Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street within walking distance of downtown, the United States Naval Academy, and the Navy and Marine Corps Stadium, this delightful space features a tranquil screened front porch, inviting living and dining areas, and two bedrooms (one queen, two twin beds) with all bedding and linens provided. The lower level offers a full-size futon and a designated office area for added comfort and convenience.

Enjoy the convenience of two bathrooms stocked with essentials and a hair dryer. The well-equipped, spacious kitchen includes amenities such as a fridge, stove, toaster, microwave, coffee machine, and dishwasher. Additionally, access a washer and dryer, central AC, high-speed internet/Wi-Fi, and three smart TVs with Roku and Fire TV for cable channel streaming.

Step outside to a charming garden area furnished with a BBQ grill, patio set, and parking for two cars. Feel free to reach out as I can offer weekly, and monthly discounts as well as last minute bookings.

Guest Reviews:

- "Beautiful home and property in great location. Loved coming back after a busy day and sitting on the screened porch." - "Very clean and functional house on a very quiet street. Host was always available for questions and was very responsive." - "Such a cute little house in a great location. Maria's house was clean and very well stocked - beyond what you expect with the basics, it was extremely thoughtful. Super location, we walked everywhere during our entire stay - and the 2 parking spots were a huge bonus so we could leave our cars and not worry about finding parking at all. The street itself was quiet and quaint. Unfortunately the weather didn't allow us to use the outdoor spaces, but they looked lovely as well. Highly recommend this property!"

Anchors Away Abode
House
Annapolis, MD, USA

Anchors Away Abode is located in Annapolis, just 3.1 miles from Annapolis Harbor and 25 miles from Addison Road-Seat Pleasant. This vacation home features air-conditioned accommodations with a patio. Power Plant is 29 miles from the vacation home and Pier Six Concert Pavilion is 29 miles away. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a hair dryer. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Guests can relax near the outdoor fireplace at the vacation home. Carroll Park is 28 miles from Anchors Away Abode, while Sports Legends Museum at Camden Yards is 28 miles from the property. Baltimore - Washington International Airport is 19 miles away.

Guest Reviews:

- "Cozy and cute"

Cozy 2br home w/parking in downtown Annapolis
House
Annapolis, Maryland, USA

A's by the Cove is ideally located in the heart of downtown Annapolis's Historic and Art Districts. It is a fully updated & detached home with historic charm and an inviting front porch. Well conceived and open floor plan to include a living room (with queen sleeper sofa), a dedicated workspace, 1/2 bath and eat in kitchen on the first floor and 2 bedrooms and a full bath upstairs. Enclosed rear yard provides an opportunity to create a lovely quiet space out our back door.

One parking spot (in a nearby by public lot - less than 60 yard from the house) is included with your rental, you can walk to West street, Main Avenue or the city dock all in less than 10 min.

The property is equipped with a RabbitAir Air Filtering device which allow the interior air to go through a 6-stage filtering twice every hour. it traps allergens & contaminants. It is certified Asthma & Allergy friendly.

A perfect location to enjoy Commissioning Week, Boat Shows and other festivals in Historic Annapolis.

A's by the Cove has a minimum age requirement. All adult members of your party must be 21 or older unless they are children traveling as part of a family group. Every guest must be registered and verified on your reservation. We have a strict no party or gathering policy.

Guest must sign Rental Agreement and provide Government ID.

Although you have access to the entire house and private backyard, there is one locked owner closet located in the living room.

Your arrival (and departure) are fully contactless. You will be provided with detailed check-in instructions the afternoon prior to your arrival including a code and/or mobile app to enter the home.

We are here for you during your stay, but our level of interaction is entirely up to you. We are only a phone call/message away and will respond usually within minutes during extended business hours. During the overnight, we probably wont get back to you until early the next morning. If there is a life threatening emergency, please contact 911 and then call us and leave us a voicemail. We reserve the right to stop by the property at anytime but will give you at least 4 hours notice except in case of emergency.

The property is equipped with video recording camera outside the home. There are 2 cameras located on the front porch and the backyard for the safety of our guests. One on the front porch looking at the front door and one on the back porch looking at the backyard. Those are used for security purpose only. Any recording is automatically deleted after 30 days.

Third Party Reservations (Guest not occupying the home) are strictly forbidden and again any channel policy (airbnb, VRBO, booking...). The guest who made the reservation must be an active occupant of the home for the entire duration of the reservation. Unauthorized guests will be removed from the property and the reservation will be immediately canceled. No refund will be provided regardless of the cancellation policy.

Guest Reviews:

- "House was great. Very good location. Very accommodating." - "A's by the Cove is quiet and perfectly quaint. Everything is in walking distance from the water to the arts district. Great restaurants, shopping and entertainment! We walked to see a show at Rams head Tavern and had a great time!" - "This is a fantastic property in a great location. Appreciated the quick responses from owners. Hope to be back next year. Highly recommend."

USNA Home In Downtown Annapolis
Apartment
96 Clay Street, Annapolis, MD, MD 21401, USA

USNA Home In Downtown Annapolis offers accommodations in Annapolis, 1.7 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards. Both free Wifi and parking on-site are available at the apartment free of charge. Power Plant is 30 miles from the apartment and Pier Six Concert Pavilion is 31 miles away. The air-conditioned apartment consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are provided in the apartment. For added privacy, the accommodation features a private entrance. Baltimore Convention Center is 30 miles from USNA Home In Downtown Annapolis, while Inner Harbor is 30 miles away. Baltimore - Washington International Airport is 21 miles from the property.

Amenities:

Security/Safety • Pet Friendly • Internet • Parking • Guest Services • Other • Air Conditioner • Child Friendly

CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
Apartment
Annapolis, Maryland, USA

A stunning home, “Circa 1885” is a restored piece of Annapolis history. Sitting at one of the two major gateways that lead into downtown, our beautifully renovated home sits on the corner of King George and Randall Streets. A distinctive yellow PRIVATE entry door off of Randall Street leads to this rental apartment that boasts 2 large bedrooms (K, Q), family room with a cozy pull out sofa (F), 1 bath with antique claw foot tub/shower, beautiful eat-in kitchen, and beautifully restored original pine flooring throughout. Everything you need in Annapolis is within an easy walk: US Naval Academy (directly across the street), Navy-Marine Corps Memorial Stadium, Maryland State House, restaurants, shopping, City Dock, Market Place, Eastport, William Paca House & Gardens, museums, boat supplies, as well as the perfect seat to enjoy the 4th of July fireworks! An abundance of options to enjoy boating adventures on the bay or taking the Annapolis Water Taxi to dinner are all located just 2 blocks from our home. Excellent for small groups and a wonderful place to experience Historic Downtown Annapolis.

Other things to note:
*Suitable for children 6 & up
*Please no big parties or large events

Guest Reviews:

- "As everyone else has said, this is the perfect little spot in Annapolis. Location could not be better, great owner, the place was absolutely spotless, and super comfortable. We would book this place again in a heartbeat. " - "My third time at this cozy and super-perfect USNA location! Sean is very communicative and responsive. Sad that this is likely our last stay as our Midshipman will Commission in a matter of months! Cannot recommend this more!"

The Little House
House
Annapolis, MD, USA

The Little House offers accommodations in Annapolis, 1.5 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards. This vacation home offers air-conditioned accommodations with a patio. Outdoor seating is also available at the vacation home. The Little House features 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. There is an on-site restaurant. Baltimore Convention Center is 30 miles from the accommodation, while Inner Harbor is 30 miles from the property. Baltimore - Washington International Airport is 21 miles away.

Amenities:

Security/Safety • Guest Services • Laundry • Child Friendly • Fireplace/Heating • Air Conditioner • Balcony/Terrace • Restaurant

Perfect spot for a Weekend Getaway!
Apartment
Annapolis, Maryland, USA

This luxiourious apartment sits right off Main Street and is so centrally located...you can park your car in the city garage and walk to everything. Great place for entertaining and people watching! 2 Bedrooms/1 Bathroom with full kitchen. Whether you are in town for a Naval Academy function, a wedding or just touring this wonderful town...you will feel right at home in this Apartment. Email me if you have any questions.

Guest Reviews:

- "Made a last minute reservation for a birthday outing for my husband. This Apartment overlooking Main Street is a hidden gem. it was very clean and had everything we needed. Such a nicer experience than staying in a hotel. We were ready to move in! The host gave us an early check in and late check out." - "Terrific space in the center of everything. Nice to park the car for the weekend and explore on foot. Cozy apartment to hang out when we weren’t wandering or eating. Host was attentive and offered us an early checkin which was greatly appreciated. Would stay again!"

* Midcentury Modern Getaway * Prime Location *
House
54 Cornhill Street, Annapolis, MD, MD 21401, USA

Providing a garden, * Midcentury Modern Getaway * Prime Location * provides accommodations in Annapolis. With inner courtyard views, this accommodation offers a patio. Free Wifi is available throughout the property and Annapolis Harbor is 1.2 miles away. Providing access to a balcony with city views, the air-conditioned vacation home consists of 3 bedrooms. Offering a terrace with garden views, this vacation home also features a cable flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a bath and a hair dryer. For added privacy, the accommodation features a private entrance. Guests at the vacation home will be able to enjoy activities in and around Annapolis, like cycling, fishing, and hiking. Sports Legends Museum at Camden Yards is 30 miles from * Midcentury Modern Getaway * Prime Location *, while Baltimore Convention Center is 30 miles from the property. Baltimore - Washington International Airport is 21 miles away.

Amenities:

Internet • Private Beach • Fireplace/Heating • View • Entertainment • Guest Services • Ocean View • Parking • Other • Balcony/Terrace • Sports/Activities • Security/Safety

Eastport Cottage .5 mi from Downtown Annapolisnn
House
Annapolis, Maryland, USA

Charming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Chris, Boatyard, O'leary's, Carol's Creek, to name a few) and less than .5 mile from Historic Downtown Annapolis. Enjoy a weekend (or longer stay) away where everything you need is in walking distance. Start your mornings with a 2 block walk for coffee and pastries, or breakfast on the porch or deck, then wander through Eastport and Downtown Annapolis while you enjoy seasonal weather (there is always something going on), and end your day by going out to eat, or grilling on the back deck overlooking a beautiful garden and patio space at your getaway 'home'. Enjoy coffee (which is provided) or cocktails on the front porch and watch the folks and their pets stroll by!

Guest Reviews:

- "We stay in Annapolis often and love this Eastport location. This is a perfect house for a couple - and had everything we needed. Host was great to work with." - "Stayed here for five nights. Property is clean, comfortable, and is in an excellent location as we could walk anywhere in the downtown Annapolis/Eastport area. Mark was easy to communicate with. Would stay here again!" - "We enjoyed our stay at this property in Annapolis. It was a convenient walk to downtown and several great restaurants in Eastport. The house was impeccable, the beds and linens very comfortable, and the decor was beautiful. The host went out of his way to communicate restaurant ideas and other information to us and was pleasant to talk with. The owner has a locked section of the house on the back so there is no back door on the property for renters to use. We could access the backyard by going around the side of the house. The owner was not staying there during our visit and stayed at his other property. He did need to stop by while we were renting but communicated that via text so we would know when he would be on the property. The wine bar and bakery close to the house were lovely and the ease of parking in the roomy driveway was wonderful!"

The Ship's Bridge
House
Annapolis, MD, USA

The Ship's Bridge offers accommodations in Annapolis, a few steps from Bay Ridge Beach and 5 miles from Annapolis Harbor. This beachfront property offers access to a terrace. Outdoor seating is also available at the vacation home. The air-conditioned vacation home is composed of 4 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 4 bathrooms. Towels and bed linen are available in the vacation home. There's also a seating area and a fireplace. Guests are welcome to enjoy a meal at the on-site restaurant. Addison Road-Seat Pleasant is 29 miles from The Ship's Bridge. Baltimore - Washington International Airport is 24 miles from the property.

Amenities:

Laundry • Sports/Activities • Air Conditioner • Barbecue/Outdoor Cooking • Fireplace/Heating • Oceanfront • Ocean View • Balcony/Terrace • Restaurant • View • Guest Services • Security/Safety

Bay View Studio Apartment
Apartment
Annapolis, Maryland, USA

Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private patio, and hot tub! 50 ft of waterfront make this private walk-out garden-level apartment nestled in a small wooded oasis near downtown Annapolis a gem. Walk to the marinas or the Sailing School to catch a water taxi to downtown or book a private sail or fishing tour. Walk to Port Annapolis to get some fresh baked goods at Black Market Bakery.

Access the large 1000+ sf private apartment from a rear separate entrance of this owner-occupied home. There is dedicated space for 2 cars at the end of the driveway.

The King bed is spacious. The Queen sleeper sofa by American Leather is the most comfortable on the market. Note that this apartment is a studio, and the bedroom is open to the living space and queen sleeper sofa.

Enjoy high speed internet during your stay. Watch your shows on the flat screen TV using your streaming accounts (there is no cable; bring your passwords to log in to your favorite steaming channels such as Netflix, AppleTV, Amazon Prime, YouTube, etc.). There is an XBOX and a large collection of DVDs for some old-school movie thrills.

IMPORTANT NOTE REGARDING INSURANCE: When you book with VRBO, you should see an option for either paying an insurance fee (flat rate ~$59) or submitting a refundable deposit. Choose whichever option best suits you. These transactions are with VRBO, not the host.

Guest Reviews:

- "Gorgeous views and relaxing. Perfect for a weekend getaway right on the water." - "The property was larger than expected and very comfortable. The views are incredible of the Bay Bridge with beautiful sunrises. It is wonderfully secluded yet close to the Naval Academy and all Annapolis has to offer. Laura, the property owner was very professional and wonderful to work with. We will be back!" - "We loved our stay! The owner was easy to communicate with a spectaular view. Our family loved watching the deer and ducks every morning and evening. We were also in walking distance to the water taxi for easy communtes into Annapolis. Jeannie L"

The Compass Rose by Leavetown Vacations
House
1140 Bay Highlands Dr, Annapolis, MD, 21403, USA

Featuring a garden, The Compass Rose by Leavetown Vacations features accommodations in Annapolis. This property offers access to a patio, table tennis, free private parking, and free Wifi. Outdoor seating is also available at the vacation home. The air-conditioned vacation home consists of 5 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 3 bathrooms with a shower and a hair dryer. Towels and bed linen are available in the vacation home. There's also a seating area and a fireplace. Annapolis Harbor is 4.2 miles from The Compass Rose by Leavetown Vacations, while Addison Road-Seat Pleasant is 28 miles from the property. Baltimore - Washington International Airport is 23 miles away.

Amenities:

Balcony/Terrace • Accessibility • Guest Services • View • Parking • Internet • Security/Safety • Air Conditioner • Sports/Activities • Fireplace/Heating • Barbecue/Outdoor Cooking • Other

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Apartment
Annapolis, Maryland, USA

Charming private space in a quiet neighborhood. Live like locals and enjoy walking or biking around town. Free street parking, one block to Navy Stadium, 1 mile walk to downtown Annapolis and Naval Academy, 30 min drive to Baltimore or BWI and 45 min to Washington DC.
Beautiful, immaculate private space.
Safely tucked away a charming carriage house apartment in private backyard - 2 bedrooms, family room, well equipped kitchen and sparkling clean shower and bath.
Pets welcomed but must be approved in advance +$50 pet fee per pet, per stay.
Note - 7 night min. during USNA Commissioning Week.
2 night minimum preferred, but will accept one night bookings.
Plenty of toys for toddlers and babies, games for older kids. Highchair and pack & play.
We have several bicycles available to use, different sizes for different ages, please ask.
Outdoor space in the yard for toddlers to play. Also ask for corn hole and other yard games to use.
Cozy fire pit area to enjoy, please ask for wood or bring your own.
School fields near by and beautiful nature walking path right in front of the house. Please use the path for all pet bathroom needs not the backyard space.
Hope you enjoy and relax in Annapolis!

Guest Reviews:

- "This was a perfect place for the 4 of us to use as our "home base" while touring Annapolis. It is dog friendly and is located by some very nice walking trails. It has a small outside area that we enjoyed in the evening & for coffee in the morning. The apartment was very well stocked, and the owners were very responsive & helpful. We would not hesitate to book again." - "My family stayed for Induction Day at the Naval Academy. Said they wished they could have stayed longer! Lovely, clean and convenient. Ingrid was so helpful with info, kind, accommodating and communication was a breeze. We definitely hope to stay again! Go, Navy!"

Anchors Aweigh
House

Anchors Aweigh is located in Annapolis, just 1.2 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards. This vacation home offers air-conditioned accommodations with a patio. Baltimore Convention Center is 30 miles from the vacation home and Inner Harbor is 30 miles away. The vacation home features 4 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with free toiletries. Towels and bed linen are featured in the vacation home. For added privacy, the accommodation features a private entrance. Guests may eat at the on-site restaurant. Power Plant is 31 miles from Anchors Aweigh, while Pier Six Concert Pavilion is 31 miles away. Baltimore - Washington International Airport is 21 miles from the property.

Amenities:

Fireplace/Heating • Air Conditioner • Security/Safety • Laundry • Sports/Activities • Restaurant • Barbecue/Outdoor Cooking • Child Friendly • Guest Services

Historic District"Crab Cakes and Football"
House
Annapolis, Maryland, USA

Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock and the Navy-Marine Corps Memorial Stadium. Private parking for 2 cars!

There are seven restaurants within one block including:
- Thai
- Italian
- Irish
- Unique Annapolis Fare

This is the perfect spot to enjoy all that Annapolis has to offer. People who know the area know that having 2 parking spots is almost unheard of. We are located in one of the most sought after neighborhoods in Annapolis. The neighborhood has a very peaceful, quiet feel. The property had once been a long term rental but we decided we'd rather share it with people coming here to vacation. We live 5-10 minutes from the property so you can enjoy your privacy but we are available if you need us.

Guest Reviews:

- "We had the best stay! My husband I took a short weekend trip with our dog. Liz was so accommodating and even left us wine and chocolates to celebrate. She was so nice and even let us stay as long as we wanted on Sunday!" - "We stayed here for our son’s Iday and it could not have been more perfect. It was a comfortable walk to Gate 1 and DTA. Liz was very accommodating with check in and check out times and all of the special touches made our stay that more comfortable. We will definitely stay here again!"

Bella Chateau
House
Annapolis, MD, USA

Bella Chateau offers accommodations in Annapolis, a 9-minute walk from Bay Ridge Beach and 4.4 miles from Annapolis Harbor. This vacation home features air-conditioned accommodations with a patio. On clear days, guests can head outside to enjoy the vacation home's outdoor fireplace or simply kick back and relax. The vacation home features 6 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 4 bathrooms with a hair dryer. Towels and bed linen are available in the vacation home. There's also a seating area and a fireplace. Guests are welcome to eat at the on-site restaurant. The vacation home has a picnic area where you can spend the day outdoors. Addison Road-Seat Pleasant is 29 miles from Bella Chateau. Baltimore - Washington International Airport is 24 miles from the property.

Amenities:

Laundry • Sports/Activities • Restaurant • Security/Safety • Air Conditioner • Child Friendly • Balcony/Terrace • Barbecue/Outdoor Cooking • Fireplace/Heating • Pet Friendly • Guest Services

Stay in Heart of Downtown Annapolis Steps to Main St at Historic Carriage House
House
Annapolis, Maryland, USA

Experience the Difference: Professionally Managed by iTrip Annapolis
Originally built in 1857, this fully-restored home has a rich history that's been documented from it's original purpose as a Horse Barn and later became a popular hotel, due to its location in the center of the City, along with the neighboring townhouses on the block. As part of the larger City Hotel complex, this row house block is a rare example of early 19th century commercial domestic architecture which retains a high degree of integrity and contributes significantly to the pivotal intersection of Duke of Gloucester and Conduit streets. In 1900 the rowhouse block was sold independently in 1903 to Weems and Grafton D. Ridout, in whose family the building remained until the mid twentieth century.

When entering the home, you will be greeted by both the historic charm and all of the upgraded amenities that make for a modern experience. Walk through the impeccably-decorated living and dining rooms into the stunning kitchen with all stainless steel appliance and beautiful granite kitchen counters. Even the breakfast bar seating is an example of the owners' attention to beautiful decor. Head out the glass door in the kitchen to the private fenced-in back patio with lounge chairs and a BBQ. Also on the main floor is a European-inspired full bath with a small stand-up shower.

Upstairs are 2 bedrooms and 1 full bath, the 2nd full bath is located on the first floor (and is a small European-style bath). There's a King bed in the Main bedroom, a Queen in the guest room and the sofa in the Den that pulls out to a full bed. There's also a flatscreen TV and sunny desk space in the Den.

Walk Score 100 - When you're ready to explore Annapolis, you are just 1/2 a block to the shops and restaurants on Main Street, 2 blocks to the waterfront and 3 blocks to the Naval Academy! While the home does not have dedicated parking, it is conveniently located, via walkway, to the Hillman garage.

SLEEPING ARRANGEMENTS 2 BR / 2 BA / Sleeps 6:
Main King Bedroom:
- 2nd Floor
- King Bed
- Full Bath in the Hall or downstairs

Guest Bedroom:
- 2nd Floor
- Queen Bed
- Full Bath in the Hall or downstairs

Upstairs Den
- 2nd Floor
- Full Sofa Bed
- Flat Screen TV
- Full Bath in the Hall or downstairs

HIGHLIGHTS:
- Private Patio fenced in the back yard with propane BBQ grill
- Full gourmet kitchen
- Breakfast bar seats 4
- Dining room table seats 4
- WiFi
- Big Screen TV's
- Double-facing decorative fireplaces
- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
- Washer & dryer located inside the home
- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.
- Keyless entry. Drive straight to your rental home and enter the door with an electronic lock code.

Property Distance to:
- Main Street Annapolis - 1 block
- U.S. Naval Academy – 3 blocks; 8 minute walk
- Washington, DC – 30 miles
- Baltimore - 25 miles

* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.
* All beds are ready made for you with freshly laundered sheets & towels.

House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.
Check-in time: 4:00 pm
Check-out time: 11:00 am

Guest Reviews:

- "Beautiful home, very nice furnishings, in THE perfect location! Close to everything! Ready to go back" - "I feel like this place deserves more than 5 stars: the place was immaculate, beautifully yet comfortably furnished, steps away from main street and just perfect for a quick weekend away with friends. All communication was smooth and easy. My only regret is that I didn't get a chance to try out the super cool shower room on the first level. If/when we go back, we're definitely staying here!"

The Admiral's Retreat
House
Annapolis, MD, USA

The Admiral's Retreat is located in Annapolis, just 1.1 miles from Bay Ridge Beach and 4.6 miles from Annapolis Harbor. Offering a restaurant, the property also has pool with a view as well as a hot tub. On clear days, guests can head outside to enjoy the vacation home's outdoor fireplace or simply kick back and relax. Offering direct access to a balcony with pool views, the spacious air-conditioned vacation home consists of 6 bedrooms. Featuring a terrace with lake views, this vacation home also includes a satellite TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 5 bathrooms with a hot tub and a hair dryer. There's also a seating area and a fireplace. The vacation home has a picnic area where you can spend the day outdoors. Addison Road-Seat Pleasant is 29 miles from the vacation home. Baltimore - Washington International Airport is 24 miles from the property.

Amenities:

Guest Services • Sports/Activities • Barbecue/Outdoor Cooking • Wellness Facilities • Restaurant • Laundry • Security/Safety • Air Conditioner • Balcony/Terrace • Pool • Hot Tub • View

Pristine Downtown 1-Bedroom Steps from State House
Apartment
Annapolis, Maryland, USA

Enjoy your stay in the heart of Annapolis's historic district, steps away from the Maryland State House and a few minutes walk to the Naval Academy (6 mins), downtown waterfront (4 mins), shops on Maryland Ave (2 mins), and West Street (7 mins).

This is a historic home built by Eleanor Hepburn, the cousin of actress Katharine Hepburn. Look out for the "EH" on the door.

It has been newly renovated from top to bottom and has everything you need for a short- or long-term stay!

One-bedroom ground-floor apartment with a comfortable full bed, a queen pull-out sleeper sofa in the living room, in-unit washer and dryer, and a fully equipped kitchen.
All rooms include darkening shades.

This apartment is completely private and has its own entrance. Limited street parking permits are available on request.
Please know that there is some noise in the area during the day as we are located right in the heart of Downtown Annapolis.

Guest Reviews:

- "Fantastic, cozy little gem in the heart of Annapolis with everything you need." - "Can’t say enough about this property, the host were amazing and got back to us right away and even checked in to make sure we didn’t need anything. The location was within walking distance of everything and the actual property was so nice inside and had everything we needed. We will definitely stay here again in the future!" - "Wonderful location, close to restaurants, bay and shop. Lovely apartment for two."

The Master Shipwright
House
Annapolis, MD, USA

The Master Shipwright is located in Annapolis, just 1.1 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards. With river views, this accommodation features a terrace. There's a restaurant. The air-conditioned vacation home is composed of 4 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 5 bathrooms. Towels and bed linen are available in the vacation home. The property has an outdoor dining area. Baltimore Convention Center is 30 miles from the vacation home, while Inner Harbor is 31 miles from the property. Baltimore - Washington International Airport is 21 miles away.

Amenities:

Child Friendly • Restaurant • Pet Friendly • Barbecue/Outdoor Cooking • Security/Safety • Air Conditioner • Balcony/Terrace • Laundry • Fireplace/Heating • Sports/Activities • Guest Services

Charming Historic Townhouse Steps From USNA
House
Annapolis, Maryland, USA

Welcome to our charming home nestled next to the prestigious Naval Academy in Annapolis. This inviting 1-bedroom, 1-bathroom accommodation is ideally located within walking distance to downtown, allowing you to explore the city's historic charm and vibrant atmosphere at your leisure.

Situated across from the renowned St. John's College, our home offers a picturesque setting with its close proximity to lush green spaces and breathtaking views. Step inside, and you'll find a cozy yet spacious interior that comfortably accommodates up to 4 people.

The bedroom features two comfortable queen beds, providing a restful night's sleep for guests. Additionally, there's a convenient pullout couch in the living area, perfect for extra guests or family members. The tastefully decorated space exudes a welcoming ambiance, ensuring your stay is both relaxing and enjoyable.

In addition to its prime location and comfortable accommodations, our home boasts a full kitchen equipped with all the amenities you need for a convenient and enjoyable stay. Whether you're a culinary enthusiast or simply prefer the convenience of preparing your own meals, our kitchen is fully stocked with appliances, cookware, and utensils.

Furthermore, we understand that staying connected and having access to clean clothes are important during your travels. That's why our home includes a washer and dryer, allowing you to conveniently refresh your wardrobe as needed.

Whether you're here for a weekend getaway, attending events at the Naval Academy, or exploring the charm of downtown Annapolis, our home provides a delightful home away from home. Book your stay with us and experience the perfect blend of comfort, convenience, and proximity to all that Annapolis has to offer.

Guest Reviews:

- "Loved this place -- walking distance to virtually everything in Annapolis. Very clean, cute, comfortable. Highly recommend." - "I loved staying at this property. It was a short walk into town. The property was well appointed." - "This condo is absolutely beautiful & the location was perfect for our daughter’s wedding at the naval academy chapel. We loved this unit. It has everything you need including a full kitchen & was walkable to everything. Check in was very easy & convenient. It’s a wonderful place to stay in Annapolis!"

Inn on Main Annapolis
Bed & Breakfast
165 Main Street, Annapolis, MD, MD 21401, USA

Inn on Main Annapolis enjoys a location in Annapolis, 30 miles from Inner Harbor and 31 miles from Power Plant. The property is around 1.2 miles from Annapolis Harbor, 30 miles from Sports Legends Museum at Camden Yards, and 30 miles from Baltimore Convention Center. The bed and breakfast offers a restaurant serving American cuisine, as well as free Wifi throughout the property. All units feature air conditioning and a flat-screen TV. The rooms come with a private bathroom with a shower and a hair dryer. At the bed and breakfast, the units come with bed linen and towels. There is a coffee shop, and packed lunches are also available. Dining options are available close to the bed and breakfast. Guests at Inn on Main Annapolis will be able to enjoy activities in and around Annapolis, like cycling. Pier Six Concert Pavilion is 31 miles from the accommodation, while Harbor East Marina is 31 miles away. Baltimore - Washington International Airport is 21 miles from the property.

Guest Reviews:

- "Great location in downtown Annapolis, can’t wait to go back!" - "The perfect location with friendly staff." - "Great location!! Friendly staff!" - "It was nice stay, staff was very attentive, breakfast was delicious!" - "The room was on the third floor and small, but it was clean and the people were friendly! Nice!" - "Great location, great staff. Rooms are basic but fine."

Cozy 1st Floor King George one bedroom apartment right across from USNA
Apartment
Annapolis, Maryland, USA

Enjoy this one bedroom first floor apartment that's right across from Gate 2 of the U.S. Naval Academy. It's a short 1 block walk onto the USNA yard and 2 blocks to get to all of the restaurants, shops and water taxi on Ego Alley and everything that downtown Annapolis has to offer on Main Street and in Eastport. There are 8 steps to go up to get into the front entrance. Once you enter the front entrance there are no steps to enter the apartment. The apartment has a fully updated kitchen if you'd like to eat in, with a microwave, stove and dishwasher. The full bath has been completely remodeled. This home offers the charm of a historic home with modern day conveniences. Before the recent updates were made Walter Cronkite even stayed in the unit in the early 80's when his sailboat was downtown!

Check in is after 4pm. If we can accommodate an earlier check in we will.

Guest access:
You will have full access to the one bedroom first floor apartment. In addition you have access to shared washer and dryer located in the basement and a shared courtyard and grill out back.

Other things to note:
There is a queen size bed in the bedroom and a queen size pull out couch in the living room.

Guest Reviews:

- "Couldn't have chosen a better location for our two night stay. Nice clean apartment unit, well supplied with everything we needed. The owner, Julie, was very helpful and easy to communicate with. I would highly recommend!" - "Clean and close to everything. Perfect location to relax and walk to restaurants and stores. Condo was clean. It was an overall a great stay." - "This is a great place in a perfect location! We parked at the Noah Hillman garage ($22 per 24 hours) and it was an easy walk. The apartment is well kept and cute! The grill is good and the pullout sofa bed is really comfortable. Our kids slept on it, but adults could easily stay on it without comfort issues. Tons to see and do in the area. We drove into DC a few days and it took around an hour. We went to Sandy Point Park a few times to go swimming in the bay and it was a cheap, family friendly park and beach. The hosts answered any questions almost immediately and are always available. We had a great stay!"

Spectacular Location Two Bedroom State Circle Apartment
Apartment
94 State Circle, Annapolis, MD, MD 21401, USA

Spectacular Location Two Bedroom State Circle Apartment offers accommodations in Annapolis, 1.5 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards. The property is around 30 miles from Baltimore Convention Center, 30 miles from Inner Harbor, and 30 miles from Power Plant. Free Wifi is available, and private parking can be arranged at an extra charge. The air-conditioned apartment consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are featured in the apartment. For added privacy, the accommodation features a private entrance. Guests can also relax in the garden. Pier Six Concert Pavilion is 31 miles from the apartment, while Harbor East Marina is 31 miles away. Baltimore - Washington International Airport is 21 miles from the property.

Guest Reviews:

- "This was a very comfortable nicely furnished apartment in a great location" - "Perfect place for a special family celebration." - "Perfect!" - "Overall, this property worked out well for our specific needs on this visit to Annapolis." - "A very nice place for the cost at a great location."

All-stop. Rental Midships.
House
Annapolis, Maryland, USA

Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome steps away from Gate One, City Dock Waterfront, and all the attractions that Historic Downtown Annapolis has to offer.

Settle into this spacious, well-appointed townhome in the heart of Downtown Annapolis. This detached townhome, professionally cleaned and beautifully maintained, is the perfect lodging for USNA families and events, wedding parties, and weekend explorers.

Enjoy your morning coffee in the quiet courtyard and, when the sun's passed the yardarm, your evening brightener on the third-floor deck, which boasts a view of the Naval Academy Chapel! If sipping a whiskey while lounging on a deep leather sofa or a Churchill armchair is more your speed, the main deck living space is the place to relax. Should you desire to escape the hustle and bustle of Randall St-tuck in and watch a movie, play a video game on the PS4, or read a book in the topside living room.
Should the inspiration to cook strike, the kitchen boasts new appliances, a chef's quality knife set, and cooking ware. In addition, groceries are just a click away from Instacart and Whole Foods Delivery through the Amazon app!

Eventually, when the time comes to turn in, the bedrooms have taken care of your comfort needs. Down pillows, cozy comforters/quilts, and soft bathroom linens make decompressing from a long day of exploring Annapolis easy. The main bedroom has a queen bed, an ensuite bathroom, and a room-length closet for all your organization needs. The forward guest bedroom has a queen bed, a brass crib, and a separate bathroom with a combination tub/shower.

Due to a change in city regulations, unlimited parking passes for residential street parking can no longer be provided to guests. We provide one 24-hour pass for stays under three nights and two passes for four nights or more. However, you may pay to park on the street for up to 3 hours. In addition, the city does provide free parking from 6 PM Friday to 6 AM Monday at the Calvert Street Garage (19 St. Johns Lane).

You can also park in the following garages/lots:

-South Street Lot (South Street, off Church Circle; $15/day; 10-minute walk to house)
-Gotts Court Parking Garage (25 Northwest Street; $15/day; 13-minute walk to house).
-CURRENTLY UNDER CONSTRUCTION, OPENING SUMMER 2023-Hillman Garage (150 Gorman Ave, entrances from Main Street or Duke of Gloucester; $20/day; 5-minute walk)
*The free Annapolis Circulator bus stops at all the city garages/lots and City Dock (closest stop to the house) and can be used to get to/from the garages. Please view the Annapolis Parking and Access Annapolis websites for further details.

License #: STR21-144994

Guest Reviews:

- "This lovely historic house is directly across from the Naval Academy while the shops and restaurants of Annapolis start a mere block away. The location couldn't be better or more convenient. We thoroughly enjoyed all aspects of the home, including comfy bedrooms, third floor great room, excellently appointed kitchen and top deck views. No car was needed. The host is very responsive and helpful. We look forward to calling this home again in the future."

USNA Home Downtown Annapolis
Villa
96 Clay Street, Annapolis, MD, MD 21401, USA

USNA Home Downtown Annapolis is located in Annapolis, just 1.7 miles from Annapolis Harbor and 29 miles from Carroll Park. Both free Wifi and parking on-site are available at the villa free of charge. Historic Ships in Baltimore is 30 miles away and Inner Harbor is 30 miles from the villa. The air-conditioned villa consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are featured in the villa. For added privacy, the accommodation features a private entrance. Guests can also relax in the garden. Sports Legends Museum at Camden Yards is 30 miles from USNA Home Downtown Annapolis, while Baltimore Convention Center is 30 miles away. The nearest airport is Baltimore - Washington International Airport, 21 miles from the accommodation.

Guest Reviews:

- "Amazing Value!"

Tranquility Awaits
Apartment
Annapolis, Maryland, USA

Entire Guest House. One bedroom, one bathroom with loft. Three beds, queen, full and twin. Full kitchen, laundry, dedicated work space with docking station, 2 smart TVs. On site free parking. Close to major highways, BWI Airport, Downtown Annapolis, Washington DC, Baltimore, Westfield Mall, Navy Stadium, Renaissance Festival, Eisenhower Golf Course.

The space
There is 750 square foot of living space including the loft. You have your own private entrance, washer and dryer, water heater, and HVAC unit operated by a Nest thermostat. The only thing shared is the water, electricity and the backyard.

Our tap water is totally the best! You must try it before you bring bottled water.

The kitchen is equipped with everything you would need to stay at home and cook dinner or even bake cookies.

Our sprawling backyard is great for frisbee or football.
We have a fire pit and propane grill you can use.

In the summer, I'm happy to share fresh vegetables and greens for your salad.

Guest Reviews:

- "Everything was great. Perfect place to unwind during down time of a wedding weekend downtown. Sally was super accommodating of our family, and easy to contact with any questions" - "I stayed with my husband and baby and 2 dogs and it was perfect for us without being crammed. The area is really beautiful and quiet. Easy 15 minute ride into downtown Annapolis. They were great hosts." - "Sally and Jeremy were fantastic hosts and provided everything we needed. Their apartment was clean and perfectly located for our stay. They also were very accommodating when our midshipman had to stay a few nights. I would rent again with no hesitation."

Cozy 2br home w/parking in downtown Annapolis
House
108 South Street, Annapolis, MD, MD 21401, USA

Cozy 2br home w/ parking in downtown Annapolis offers accommodations in Annapolis, 30 miles from Sports Legends Museum at Camden Yards and 30 miles from Baltimore Convention Center. The air-conditioned accommodation is 1.4 miles from Annapolis Harbor. The accommodation provides a 24-hour front desk and full-day security for guests. With free Wifi, this 2-bedroom vacation home offers a cable flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Guests can enjoy a meal on an outdoor dining area while overlooking the garden views. The vacation home offers bed linen, towels, and laundry service. There is an on-site coffee shop. Guests at the vacation home will be able to enjoy activities in and around Annapolis, like cycling. A baby safety gate is also available at Cozy 2br home w/ parking in downtown Annapolis, while guests can also relax in the garden. Inner Harbor is 30 miles from the accommodation, while Power Plant is 31 miles from the property. Baltimore - Washington International Airport is 21 miles away.

Guest Reviews:

- "Great spot to stay with parking!"

Downtown Annapolis History Holiday Style Next to City Dock with Street Parking
House
Annapolis, Maryland, USA

Enjoy the holidays in style! Welcome to the historic Strohm House, just half a block from Main Street and the City Dock, with the U.S. Naval Academy only steps away — with street parking included! Located in the heart of downtown Annapolis, this three-story 1870 Victorian offers the perfect blend of classic charm and tasteful updates. Outside enjoy multiple spots to relax including the front porch, second floor balcony, or brick patio in the fenced in backyard. Matthew Strohm was the first boxing instructor at the USNA.

Step inside to discover a thoughtfully curated historically registered home, full of warm colors, enticing artwork, and inviting spaces. The first floor features a cozy living room with elegant decor, a dining room filled with natural light and sophistication, and a cheerful breakfast nook off the recently updated kitchen — the perfect spot for morning coffee or evening conversation.

Upstairs, the second floor offers two bedrooms, one with access to a private balcony overlooking the brick patio and tree-lined backyard — where you can sip wine or read a book. A full bath with jacuzzi sits in between the bedrooms.

Make your way to the third floor with its private bedroom suite and charming little full bath, where you can glimpse at the Maryland State House dome over the treetops.

Enjoy multiple outdoor spaces designed for unwinding and reconnecting. Watch the world go by from the covered front porch, take in the breeze from a second-floor bedroom balcony, or lounge on the brick patio with a view of the deep backyard filled with trees, hydrangeas and haste plants -- offering a rare oasis in the heart of the historic district. A Weber Spirit II gas grill is located on the patio to help make delicious meals along with new memories.

Located in one of the most desirable neighborhoods in Annapolis, you’re just steps from the vibrant waterfront, top-rated restaurants, boutique shops, and centuries of history with this end rowhome. Whether you're visiting for a Naval Academy event, a romantic getaway, or simply to experience the charm of Maryland’s capital, this home offers the perfect launchpad for your stay.

Bedrooms and bathrooms breakdown:

-2nd floor bedroom #1: Full bed and trundle with 2 twin mattresses (one up one down)
-2nd floor bedroom #2: Queen bed (with balcony overlooking backyard)
-Full bath with jacuzzi in between 2nd floor bedrooms.
-3rd floor bedroom: Full bed and small full bathroom with standup shower.
-Half bath on main floor.

Living area and all bedrooms include TVs with streaming services such as Sling TV, HBO Max, Netflix, Hulu and YouTube.

Please note that the house is historic with narrow staircases and three levels.
Guest access
Guests use the entire property except the locked cellar and two owners closets inside the house.

****Parking Information****
Includes neighborhood street parking for up to 2 vehicles during your stay. Additional vehicles can use the Hillman Garage for paid parking — by the hour or per day — it's right around the corner from the house.

House readiness: No need to bring any linens -- and the house will be stocked with supplies that should last at least a few days (paper towels, laundry detergent, etc.).

Amenities:

Tv • Hot Tub • Laundry • Bedding/Linens • Kitchen • Other • Fireplace/Heating • Air Conditioner • Pet Friendly • Security/Safety • Wellness Facilities • Internet

Downtown Annapolis King George 3rd Floor Hideaway
Apartment
165 King George Street, Annapolis, MD, MD 21401, USA

Downtown Annapolis King George 3rd Floor Hideaway is located in Annapolis, just 30 miles from Inner Harbor and 31 miles from Power Plant. 30 miles from Sports Legends Museum at Camden Yards and 30 miles from Baltimore Convention Center, the property offers a garden and barbecue facilities. Free Wifi is available throughout the property and Annapolis Harbor is 1.4 miles away. The air-conditioned apartment is composed of 1 separate bedroom, a living room, a fully equipped kitchen with an oven and microwave, and 1 bathroom. Towels and bed linen are featured in the apartment. The accommodation is non-smoking. Baltimore - Washington International Airport is 21 miles away.

Guest Reviews:

- "Lovely stay with a sour ending"

Renovated 3BR Home Near Sandy Point & Annapolis
House
Annapolis, Maryland, USA

Summary:
Recently renovated 3BR, 2.5BA home just 2 miles from Sandy Point State Park & 7 miles from Downtown Annapolis. Enjoy spacious bedrooms, spotless bathrooms, and a large basement with a pull-out sofa for extra guests. Relax on the deck with grill & outdoor seating or unwind in the quiet, private fenced backyard. Free parking included. Perfect for families or groups seeking comfort, privacy, and easy access to local attractions.

The Space:
Bedrooms:
Three spacious and comfortable bedrooms, each thoughtfully furnished to ensure a restful night’s sleep. Fresh linens, pillows, and blankets provided.

Bathrooms:
2.5 clean and modern bathrooms, stocked with fresh towels, hand soap, and other essentials for your stay.

Kitchen:
A fully equipped kitchen with modern appliances, cookware, dishes, and utensils. Perfect for preparing meals at home. Includes refrigerator, stove, oven, microwave, and coffee maker.

Living Room:
A welcoming space to relax and spend time together. Comfortable seating and a large TV for entertainment.

Basement:
A spacious lower level with a large sectional sofa that converts into a pull-out bed, providing extra sleeping space for guests.

Outdoor Living:
Step onto the deck to enjoy outdoor dining with a grill and comfortable seating. The private, fenced backyard offers a peaceful retreat, perfect for relaxing after a day of exploring.

Parking:
Free parking on-site for multiple vehicles.

Location:
Just 2 miles from Sandy Point State Park for beach days and outdoor fun, and 7 miles from Downtown Annapolis with shops, dining, and historic attractions.

Guest Access:
Front door with code

The Neighborhood:
Quiet neighborhood

Interaction with Guests:
Reach out via call or text whenever

Amenities:

Bedding/Linens • Internet • Laundry • Tv • Barbecue/Outdoor Cooking • Kitchen • Other • Air Conditioner • Parking • Fireplace/Heating • Security/Safety • Balcony/Terrace

Skyline Sanctuary
House
Annapolis, MD, USA

Skyline Sanctuary is located in Annapolis, just 1.1 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards. Guests can benefit from a patio and an outdoor fireplace. Outdoor seating is also available at the vacation home. The air-conditioned vacation home is composed of 2 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. Towels and bed linen are provided in the vacation home. For added privacy, the accommodation features a private entrance. For guests with children, Skyline Sanctuary provides a baby safety gate. Baltimore Convention Center is 30 miles from the accommodation, while Inner Harbor is 30 miles away. Baltimore - Washington International Airport is 21 miles from the property.

Amenities:

Fireplace/Heating • Child Friendly • Security/Safety • Guest Services • Balcony/Terrace • Laundry • Air Conditioner

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
House
Annapolis, Maryland, USA

Welcome to our 2BR, 1BA Boutique Brick Beauty located in historic Eastport. This beauty is steps from downtown, the U.S. Naval Academy, shops, and waterfront dinning and less than 3 miles to the Navy-Marine Corps Memorial Stadium. This stylish and modern space offers guests with 3 levels of comfort, full kitchen, Wi-Fi, Smart TVs, full laundry and 2 off street parking spaces. Perfect for couples, small families and travel seekers. It's easy to see why you'll be able to unwind at our place.

Amenities:

Kitchen • Other • Sports/Activities • Bedding/Linens • Balcony/Terrace • Tv • Laundry • Fireplace/Heating • Pet Friendly • Entertainment • Security/Safety • Air Conditioner

Annapolis Home with Deck and Whitehall Bay Access
House
Annapolis, MD, USA

Annapolis Home with Deck and Whitehall Bay Access is located in Annapolis, just 28 miles from Carroll Park and 28 miles from Sports Legends Museum at Camden Yards. The air-conditioned accommodation is 25 miles from Inner Harbor. Free Wifi is available throughout the property and Annapolis Harbor is 7.8 miles away. The vacation home features 4 bedrooms, a fully equipped kitchen with a fridge, a washing machine, and 2 bathrooms with free toiletries. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Baltimore Convention Center is 28 miles from Annapolis Home with Deck and Whitehall Bay Access, while Korean War Memorial is 29 miles from the property. The nearest airport is Baltimore - Washington International Airport, 19 miles from the accommodation.

Amenities:

Parking • Security/Safety • Child Friendly • Other • Internet • Fireplace/Heating • Air Conditioner • Sports/Activities • Spa

Pet-Friendly & Spacious Home in Annapolis
House
Annapolis, Maryland, USA

Summary:
Spacious 4BR/2.5BA home roughly 10 mins from Downtown Annapolis - close to the action, yet tucked in a quiet neighborhood with room to relax. Perfect for groups (sleeps 10) with an open layout, stylish finishes, and a fully fenced backyard for pets to roam. Enjoy high-speed Wi-Fi, smart TVs, laundry, and plenty of free parking. Whether you're here to explore or unwind, this home is your clean, comfortable launchpad.

The Space:
Bedrooms: Four spacious bedrooms, each featuring clean, modern design and ultra-comfortable beds to ensure a great night’s sleep. Ideal for groups and families, the home comfortably sleeps 10 guests.

Bathrooms: 2.5 bathrooms, including two full baths stocked with fresh towels, essentials, and stylish finishes—plus a convenient half bath on the main level.

Full Kitchen: The open-concept kitchen is fully renovated and equipped with stainless steel appliances, all the cookware you need, and plenty of space to prepare meals for your group.

Living Room: Gather in the beautifully furnished living area with a large smart TV, perfect for movie nights or streaming your favorite shows.

Backyard + Patio: Step outside to a large, fully fenced backyard with a spacious patio—perfect for sipping coffee in the morning or hosting a relaxed evening under the stars.

Pet-Friendly: Bring your furry friends along—there’s plenty of space for them to run around in the secure backyard.

Parking: Ample free parking is available in the driveway and along the street, with room for multiple cars.

Location: About 10 minutes from Downtown Annapolis, you're close enough to enjoy restaurants, shops, and waterfront charm—yet far enough to enjoy peace and privacy in a quiet neighborhood.

Guest Access:
Entire house other than the locked storage closet in the garage.

Interaction with Guests:
Text or call is preferred if serious or immediate attention needed. Otherwise app communication is fine.

Amenities:

Balcony/Terrace • Child Friendly • Wellness Facilities • Fireplace/Heating • Bedding/Linens • Laundry • Kitchen • Air Conditioner • Security/Safety • Guest Services • Tv • Other

Downtown Annapolis King George 1st Floor Hideaway
Apartment
165 King George Street, Annapolis, MD, MD 21401

Downtown Annapolis King George 1st Floor Hideaway is located in Annapolis, just 31 miles from Inner Harbor and 31 miles from Power Plant. Housed in a building dating from 1904, this apartment is 30 miles from Sports Legends Museum at Camden Yards and 30 miles from Baltimore Convention Center. Free Wifi is available throughout the property and Annapolis Harbor is 1.4 miles away. The air-conditioned apartment is composed of 1 separate bedroom, a living room, a fully equipped kitchen, and 1 bathroom. A flat-screen TV is available. The accommodation is non-smoking. Guests can also relax on the sun terrace. Baltimore - Washington International Airport is 21 miles from the property.

Guest Reviews:

- "Exceptional host, property and location ! Would definitely stay there again !" - "Excellent option for visiting students at the Naval Academy! Convenient to everything." - "We greatly enjoy our stay and would love to stay there next time we are in town."

Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking
House
Annapolis, Maryland, USA

Welcome to your Annapolis getaway! Situated on an expansive and rare 1/2 acre homesite, this beautifully preserved home blends historic charm with modern amenities—perfect for families, friend groups, or Navy families visiting town.

Inside, the main level features two spacious king bedrooms, a full bath, a sun-filled living room, and a delightful four-seasons sunroom—ideal for morning coffee, evening wine, or movie nights on the big-screen TV.

Upstairs, you'll find three additional bedrooms, including a generous combo guest room (with an additional sitting room/bedroom). There’s also a shared full bath and a full laundry room. The entire home has recently been updated to include a modern HVAC system with mini splits and remotes in each bedroom and gathering space.

Sleeping Arrangements 5 Bedrooms, 2 Baths (Sleeps 12):
Second Floor
Family Pink King Bedroom: King bed + Twin plus Twin Trundle
Tan & White Guestroom: King bed
Gray Guestroom: King bed
Full bath in the Second Floor Hallway

Main Floor
Black & White Guestroom: King bed
Anchor Guestroom 2: King bed
Shared full bath on the Main Floor hallway

Home Highlights:
Fully equipped kitchen with stainless steel appliances
Multiple hangout spaces with Flatscreen TVs: Living room, and Four-seasons sunroom with flatscreen Smart TV
High-speed WiFi + 3 large Smart TVs
Driveway parking for multiple vehicles
Washer/dryer for guest use
Luxury linens + complimentary starter toiletries and paper products
Dog-friendly (with $150 non-refundable pet fee per pet)

Location - Walkable to it all!
Navy-Marine Corps Memorial Stadium – 0.7 miles
U.S. Naval Academy – 1.8 miles
Downtown Annapolis shops & restaurants – 1 mile
Washington, D.C. – 32 miles
Baltimore – 31 miles
Skip the parking hassles and walk to parades, festivals, farmers markets, waterfront events, and cozy cafes. You’ll love being in the heart of it all—without ever needing your car.

House Rules:
Primary renter must be 25+
No parties, smoking, or events
Quiet hours must be observed
Check-in: 4:00 PM | Check-out: 11:00 AM

Amenities:

Balcony/Terrace • Air Conditioner • Bedding/Linens • Parking • Tv • Other • Fireplace/Heating • Security/Safety • Kitchen • Pet Friendly • Wellness Facilities • Laundry

Private Single Family Home Close to Both Water and Downtown!
House
Annapolis, MD, USA

Private Single Family Home Close to Both Water and Downtown! is located in Annapolis, just 1.2 miles from Carrs Beach and 3.1 miles from Annapolis Harbor. This property offers access to a terrace, free private parking, and free Wifi. Addison Road-Seat Pleasant is 27 miles from the vacation home and Sports Legends Museum at Camden Yards is 31 miles away. Opening onto a patio, the vacation home consists of 4 bedrooms. The air-conditioned vacation home also provides a flat-screen TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 3 bathrooms with a bath and a shower. The property has an outdoor dining area. A children's playground is also available at the vacation home, while guests can also relax in the garden. Baltimore - Washington International Airport is 22 miles away.

Guest Reviews:

- "Wonderful stay that was so comfortable and close to everything." - "Relaxation and privacy"

The Salty Crab
House
Annapolis, MD, USA

The Salty Crab is located in Annapolis, just a 11-minute walk from Bay Ridge Beach and 4.4 miles from Annapolis Harbor. This beachfront property offers access to a patio. Outdoor seating is also available at the vacation home. The air-conditioned vacation home is composed of 3 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 4 bathrooms. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Addison Road-Seat Pleasant is 29 miles from The Salty Crab. Baltimore - Washington International Airport is 24 miles from the property.

Amenities:

Balcony/Terrace • Oceanfront • Security/Safety • Child Friendly • Ocean View • Air Conditioner • Laundry • View • Barbecue/Outdoor Cooking • Guest Services • Fireplace/Heating

Timeless Charm, Modern Comfort
House
215 Prince George Street, Annapolis, MD, MD 21401, USA

Timeless Charm, Modern Comfort is located in Annapolis, just 1.6 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards. This vacation home offers air-conditioned accommodations with a patio. Power Plant is 30 miles from the vacation home and Pier Six Concert Pavilion is 31 miles away. With free Wifi, this 1-bedroom vacation home features a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the vacation home. The accommodation has a fireplace. Baltimore Convention Center is 30 miles from the vacation home, while Inner Harbor is 30 miles from the property. Baltimore - Washington International Airport is 21 miles away.

Amenities:

Sports/Activities • Barbecue/Outdoor Cooking • Other • Guest Services • Air Conditioner • Internet • Child Friendly • Security/Safety

Unique And Central In Eastport
House
921 Boucher Avenue, Annapolis, MD, 21403, USA

Unique And Central In Eastport is located in Annapolis, just 1.1 miles from Annapolis Harbor and 26 miles from Inner Harbor. This property offers access to a patio, free private parking, and free Wifi. Power Plant is 26 miles from the vacation home and Sports Legends Museum at Camden Yards is 27 miles away. The air-conditioned vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a kettle, and 3 bathrooms with a bath and a hair dryer. Towels and bed linen are provided in the vacation home. The accommodation is non-smoking. Addison Road-Seat Pleasant is 27 miles from the vacation home, while Pier Six Concert Pavilion is 27 miles away. Baltimore - Washington International Airport is 19 miles from the property.

Amenities:

Child Friendly • Air Conditioner • Internet • Pet Friendly • Other • Fireplace/Heating • Security/Safety • Guest Services • Parking

The Jib
House
114 Conduit St, Annapolis, MD, 21401, USA

The Jib offers accommodations in Annapolis, 30 miles from Inner Harbor and 31 miles from Power Plant. The property is around 1.2 miles from Annapolis Harbor, 30 miles from Sports Legends Museum at Camden Yards, and 30 miles from Baltimore Convention Center. This air-conditioned vacation home comes with a seating area, a fully equipped kitchen with a dishwasher, and a TV. Pier Six Concert Pavilion is 31 miles from the vacation home. Baltimore - Washington International Airport is 21 miles away.

Amenities:

Parking • Child Friendly

Main Sail
House
114 Conduit St, Annapolis, MD, 21401, USA

Main Sail is located in Annapolis, just 1.2 miles from Annapolis Harbor and 30 miles from Sports Legends Museum at Camden Yards. The property is around 30 miles from Baltimore Convention Center, 30 miles from Inner Harbor, and 31 miles from Power Plant. Pier Six Concert Pavilion is 31 miles from the vacation home. This air-conditioned vacation home comes with a seating area, a fully equipped kitchen with a dishwasher, and a TV. Baltimore - Washington International Airport is 21 miles away.

Amenities:

Child Friendly • Parking

Eden on Adams
House
416 Adams St, Annapolis, MD, 21403, USA

Eden on Adams offers accommodations in Annapolis, 31 miles from Inner Harbor and 31 miles from Power Plant. The property is around a 17-minute walk from Annapolis Harbor, 27 miles from Addison Road-Seat Pleasant, and 30 miles from Sports Legends Museum at Camden Yards. This air-conditioned vacation home comes with a seating area, a fully equipped kitchen with a dishwasher, and a TV. Baltimore - Washington International Airport is 22 miles from the property.

Amenities:

Child Friendly • Barbecue/Outdoor Cooking

1879 Downtown Annapolis Home with Koi Ponds and Gardens
Villa
109 Conduit Street, Annapolis, MD, MD 21401, USA

1879 Downtown Annapolis Home with Koi Ponds and Gardens is located in Annapolis, just 30 miles from Sports Legends Museum at Camden Yards and 30 miles from Baltimore Convention Center. Guests can benefit from a patio and an outdoor fireplace. Free Wifi is available throughout the property and Annapolis Harbor is 1.2 miles away. The air-conditioned villa is composed of 1 separate bedroom, a fully equipped kitchen, and 2 bathrooms. A flat-screen TV is featured. The accommodation is non-smoking. Guests can make the most of the warm weather with the property's barbecue facilities. An indoor play area is also available at the villa, while guests can also relax in the garden. Inner Harbor is 30 miles from 1879 Downtown Annapolis Home with Koi Ponds and Gardens, while Power Plant is 31 miles away. Baltimore - Washington International Airport is 21 miles from the property.

Amenities:

Air Conditioner • Laundry • Oceanfront • Ocean View • Child Friendly • Barbecue/Outdoor Cooking • Sports/Activities • Security/Safety • Fireplace/Heating • Parking • Guest Services • Balcony/Terrace

Cozy Private Room in Annapolis 1920202
House
Annapolis

Looking to explore Annapolis and live comfortably on a budget? This place will be just right for you!
The townhouse is situated in a very convenient location! Bus stop right across the street, close to the West St, lots of restaurants and fun places, only 5 minutes3 drive to downtown Annapolis and Naval Academy!

During your stay
Housekeeping will be on staff if you need any assistance.

Cozy Private Room in Annapolis (1920203)
House
Annapolis

Looking to explore Annapolis and live comfortably on a budget? This place will be just right for you!
The townhouse is situated in a very convenient location! Bus stop right across the street, close to the west street, lots of restaurants and fun places, only 5 minutes drive to downtown Annapolis and Naval Academy!

During your stay
Housekeeping will be on staff if you need any assistance.

Amenities:

Washer • Shampoo • Shower gel • Dryer • Bedroom and laundry • Bathroom • Hangers • Hair dryer • Iron • Essentials

Nice Private Room In Annapolis 1918102
House
Annapolis

Looking to explore Annapolis and live comfortably on a budget? This private room w/ shared bath will be just right for you!
The townhouse is situated in a very convenient location! Bus stop right across the street, close to the west street, lots of restaurants and fun places, only 5 minutes drive to downtown Annapolis and Naval Academy.

Amenities:

Fire extinguisher • Smoke alarm • Lock on bedroom door • Washer • TV • Iron • Hair dryer • Carbon monoxide alarm • Air conditioning • Heating

Nice Private Room In Annapolis (1918101)
House
Annapolis

Relax with the whole family at this peaceful place to stay.

Amenities:

Smoke alarm • TV • Free parking on premises • Carbon monoxide alarm • Washer • Self check-in • Fire extinguisher • Wifi • Air conditioning

A Cottage Room in Presidents Hill
House
Annapolis

14 Hill Street was built in 1924. It is 1 block from restaurants/shops on West Street and within 1 mile of the US Naval Academy, St. John's, Ego Alley/Main Street, the USNA Stadium, the Annapolis Yacht Club and the Eastport Bridge.

Other listings for this house on Airbnb:
"An Orange Room in Presidents Hill"
"1920s House in Presidents Hill"

STR23-145301

The space
A card table and comfortable chair can be set up in the room upon request (please give a week’s notice). Presidents Hill is a very safe and neighborly community. It is quiet, yet only two city-sized blocks away from downtown Annapolis.

Guest access
The guest will have access to the 1.5 bathrooms, living room, dining room, basement and both front and back outside spaces.

During your stay
You can be as much on your own as you like or I can offer up recommendations of where you could explore. I have been living in the area for 10 years and have a lot to share!

Other things to note
Airport/Amtrak pick up potentially available for extra charge.

Parking on the street by my house is limited to 2 hours a day (hopefully useful for unloading and loading). There are 4 parking garages within a 4-minute walk.

Females and USNA affiliates preferred.

Amenities:

Free dryer – In unit • Free washer – In unit • Herbal Essence conditioner • Essentials • Cleaning products • Garden view • Herbal Essence shampoo • Bathtub • Hot water • Hair dryer

Furnished Efficiency close to Downtown Annapolis
House
Annapolis

Two room furnished efficiency apartment in Annapolis. Two miles to downtown Annapolis. Private entrance, private bath, WIFI,etc. Separate heating and A/C controls for guest.

The space
Minimalist kitchen including refrigerator, induction burner. toaster oven. etc. Not suitable for large meal preparation

Guest access
Laundry area and alternate entrance is shared.

Other things to note
Easy access to Rt 50 and Downtown DC and Baltimore
Walking distance to Truxton Park and Downtown Annapolis.
Wired High Speed Internet and WIFI
Close to Annapolis Bus Service Stop

Cozy Private Room and Bath in Annapolis (1920201)
House
Annapolis

Looking to explore Annapolis and live comfortably on a budget? This private room w/ private bathroom will be just right for you!
The townhouse is situated in a very convenient location Bus stop right across the street, close to the West St, lots of restaurants and fun places, only 5 minutes drive to downtown Annapolis ad Naval Academy.

During your stay
Housekeeping will be on staff if you need any assistance.

Amenities:

Iron • Air conditioning • Shower gel • Hair dryer • Hangers • Essentials • Dryer • Washer • Shampoo • TV

Nice Private Room In Annapolis 4-201
House
Annapolis

Looking to explore Annapolis and live comfortably on a budget? This private room w/ shared bath will be just right for you!
The single family house is situated in a very convenient location! Bus stop right across the street, close to the west street, lots of restaurants and fun places, only 5 minutes drive to downtown Annapolis and Naval Academy. THE HOUS IS ALSO AVAILABLE TO RENT. If you prefer the whole house, 20% discount will be applied!

Amenities:

Iron • Washer • TV • Exterior security cameras on property • Heating • Paid dryer – In building • Hot water • Hair dryer • Air conditioning • Smoke alarm

Nice Private Room In Annapolis 4-202
House
Annapolis

Looking to explore Annapolis and live comfortably on a budget? This private room w/ shared bath will be just right for you!
The single family house is situated in a very convenient location! Bus stop right across the street, close to the west street, lots of restaurants and fun places, only 5 minutes drive to downtown Annapolis and Naval Academy. THE HOUS IS ALSO AVAILABLE TO RENT. If you prefer the whole house, 20% discount will be applied!

Amenities:

Heating • Hot water • Hair dryer • Iron • Smoke alarm • Exterior security cameras on property • Washer • TV • Air conditioning • Paid dryer – In building

Nice Private Room In Annapolis 4-203
House
Annapolis

Looking to explore Annapolis and live comfortably on a budget? This private room w/ shared bath will be just right for you!
The single family house is situated in a very convenient location! Bus stop right across the street, close to the west street, lots of restaurants and fun places, only 5 minutes drive to downtown Annapolis and Naval Academy. THE HOUS IS ALSO AVAILABLE TO RENT. If you prefer the whole house, 20% discount will be applied!

Amenities:

Hot water • Paid dryer – In building • Air conditioning • Smoke alarm • Heating • Exterior security cameras on property • Hair dryer • TV • Washer • Iron

Historic-District Landmarks on the Map

Compare the Best Landmarks in Historic-District – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Flag House Inn 24 Randall St, Annapolis, MD, 21401, USA 432 5.0 8.9 29 Click here
Flag House Inn 26 Randall St, Annapolis, MD, 21401, USA 234 3.0 9.4 78 Click here
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity 21 Randall Street B, Annapolis, MD, MD 21401 244 4.0 9.3 12 Click here
Stunning Waterfront Cottage with Breathtaking Views! Annapolis, Maryland, USA 449 10.0 219 Click here
Annapolis Vacation Home 2 Mi to Quiet Waters Park Annapolis, MD, USA 371 4.0 9.0 12 Click here
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun! Annapolis, Maryland, USA 360 10.0 170 Click here
Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! 1709 River Road, Annapolis, MD, MD 21409, USA 358 4.0 9.6 9 Click here
Historic Downtown Charmer, Water Views and Parking! Annapolis, Maryland, USA 467 10.0 131 Click here
Waterfront Annapolis Home Fire Pit and Fishing Pier Annapolis, MD, USA 204 4.0 9.8 8 Click here
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown Annapolis, Maryland, USA 167 10.0 123 Click here
Stylish + fresh bungalow 2 blocks from N-MC Stadium Poplar Avenue 912, Annapolis, MD, 21401, USA 310 4.0 8.5 8 Click here
Craftsman Bungalow Suite Near Naval Academy Stadium and Historic District Annapolis, Maryland, USA 150 10.0 113 Click here
King George Downtown Annapolis Getaway 165 King George Street, Annapolis, MD, MD 21401 380 4.0 8.4 6 Click here
Waterfront Oasis of Annapolis Star Annapolis, Maryland, USA 443 10.0 81 Click here
Vintage Charm: Annapolis Retreat 3 Hill Street, Annapolis, MD, MD 21401, USA 365 4.0 10.0 5 Click here
Charming cottage with parking. Easy walk to downtown. Annapolis, Maryland, USA 296 10.0 77 Click here
Anchors Away Abode Annapolis, MD, USA 538 4.0 9.6 5 Click here
Cozy 2br home w/parking in downtown Annapolis Annapolis, Maryland, USA 211 10.0 72 Click here
USNA Home In Downtown Annapolis 96 Clay Street, Annapolis, MD, MD 21401, USA 262 4.0 10.0 2 Click here
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS Annapolis, Maryland, USA 354 10.0 63 Click here
The Little House Annapolis, MD, USA 208 4.0 4.0 1 Click here
Perfect spot for a Weekend Getaway! Annapolis, Maryland, USA 440 10.0 61 Click here
* Midcentury Modern Getaway * Prime Location * 54 Cornhill Street, Annapolis, MD, MD 21401, USA 304 4.0 10.0 1 Click here
Eastport Cottage .5 mi from Downtown Annapolisnn Annapolis, Maryland, USA 420 10.0 58 Click here
The Ship's Bridge Annapolis, MD, USA 426 4.0 9.0 1 Click here
Bay View Studio Apartment Annapolis, Maryland, USA 313 10.0 56 Click here
The Compass Rose by Leavetown Vacations 1140 Bay Highlands Dr, Annapolis, MD, 21403, USA 459 4.0 10.0 1 Click here
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids Annapolis, Maryland, USA 411 10.0 45 Click here
Historic District"Crab Cakes and Football" Annapolis, Maryland, USA 459 10.0 44 Click here
Bella Chateau Annapolis, MD, USA 914 4.0 9.0 1 Click here
Stay in Heart of Downtown Annapolis Steps to Main St at Historic Carriage House Annapolis, Maryland, USA 477 10.0 36 Click here
The Admiral's Retreat Annapolis, MD, USA 1200 4.0 7.0 1 Click here
Pristine Downtown 1-Bedroom Steps from State House Annapolis, Maryland, USA 233 10.0 35 Click here
The Master Shipwright Annapolis, MD, USA 1159 4.0 1 Click here
Charming Historic Townhouse Steps From USNA Annapolis, Maryland, USA 282 10.0 34 Click here
Inn on Main Annapolis 165 Main Street, Annapolis, MD, MD 21401, USA 129 3.0 8.3 316 Click here
Cozy 1st Floor King George one bedroom apartment right across from USNA Annapolis, Maryland, USA 236 9.8 33 Click here
Spectacular Location Two Bedroom State Circle Apartment 94 State Circle, Annapolis, MD, MD 21401, USA 350 3.0 8.8 19 Click here
All-stop. Rental Midships. Annapolis, Maryland, USA 558 10.0 29 Click here
USNA Home Downtown Annapolis 96 Clay Street, Annapolis, MD, MD 21401, USA 114 3.0 7.8 4 Click here
Tranquility Awaits Annapolis, Maryland, USA 177 10.0 20 Click here
Cozy 2br home w/parking in downtown Annapolis 108 South Street, Annapolis, MD, MD 21401, USA 506 3.0 7.0 4 Click here
Downtown Annapolis History Holiday Style Next to City Dock with Street Parking Annapolis, Maryland, USA 846 10.0 2 Click here
Downtown Annapolis King George 3rd Floor Hideaway 165 King George Street, Annapolis, MD, MD 21401, USA 247 3.0 8.0 3 Click here
Renovated 3BR Home Near Sandy Point & Annapolis Annapolis, Maryland, USA 326 10.0 1 Click here
Skyline Sanctuary Annapolis, MD, USA 320 3.0 10.0 2 Click here
2BR, 1BA Boutique Brick Beauty located in historic Eastport. Annapolis, Maryland, USA 289 1 Click here
Annapolis Home with Deck and Whitehall Bay Access Annapolis, MD, USA 260 3.0 1 Click here
Pet-Friendly & Spacious Home in Annapolis Annapolis, Maryland, USA 536 1 Click here
Downtown Annapolis King George 1st Floor Hideaway 165 King George Street, Annapolis, MD, MD 21401 275 8.6 8 Click here
Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking Annapolis, Maryland, USA 676 1 Click here
Private Single Family Home Close to Both Water and Downtown! Annapolis, MD, USA 467 9.6 6 Click here
The Salty Crab Annapolis, MD, USA 419 9.0 2 Click here
Timeless Charm, Modern Comfort 215 Prince George Street, Annapolis, MD, MD 21401, USA 229 1 Click here
Unique And Central In Eastport 921 Boucher Avenue, Annapolis, MD, 21403, USA 392 1 Click here
The Jib 114 Conduit St, Annapolis, MD, 21401, USA 467 1 Click here
Main Sail 114 Conduit St, Annapolis, MD, 21401, USA 482 1 Click here
Eden on Adams 416 Adams St, Annapolis, MD, 21403, USA 536 1 Click here
1879 Downtown Annapolis Home with Koi Ponds and Gardens 109 Conduit Street, Annapolis, MD, MD 21401, USA 585 1 Click here
Cozy Private Room in Annapolis 1920202 Annapolis 49 8.56 1 Click here
Cozy Private Room in Annapolis (1920203) Annapolis 49 8.8 1 Click here
Nice Private Room In Annapolis 1918102 Annapolis 49 9.54 1 Click here
Nice Private Room In Annapolis (1918101) Annapolis 49 8.44 1 Click here
A Cottage Room in Presidents Hill Annapolis 50 9.72 1 Click here
Furnished Efficiency close to Downtown Annapolis Annapolis 50 10.0 1 Click here
Cozy Private Room and Bath in Annapolis (1920201) Annapolis 52 9.18 1 Click here
Nice Private Room In Annapolis 4-201 Annapolis 54 9.66 1 Click here
Nice Private Room In Annapolis 4-202 Annapolis 54 9.4 1 Click here
Nice Private Room In Annapolis 4-203 Annapolis 54 8.54 1 Click here

Note: The prices for each Landmarks in Historic-District do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Accommodations in Historic-District that offer a pool include:

  • Stunning Waterfront Cottage with Breathtaking Views!.- Review Count: 219, Rating: 10.0
  • Waterfront Oasis of Annapolis Star.- Review Count: 81, Rating: 10.0
  • The Admiral's Retreat.- Review Count: 1, Rating: 7.0

Accommodations in Historic-District offering spa or wellness facilities include:

  • Annapolis Home with Deck and Whitehall Bay Access.- Review Count: 0, Rating: 0.0

Family-friendly accommodations in Historic-District include:

  • Stunning Waterfront Cottage with Breathtaking Views!.- Review Count: 219, Rating: 10.0
  • Annapolis Vacation Home 2 Mi to Quiet Waters Park.- Review Count: 12, Rating: 9.0
  • A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!.- Review Count: 170, Rating: 10.0

Pet-friendly accommodations in Historic-District include:

  • Waterfront Annapolis Home Fire Pit and Fishing Pier.- Review Count: 8, Rating: 9.8
  • Stylish + fresh bungalow 2 blocks from N-MC Stadium.- Review Count: 8, Rating: 8.5
  • Anchors Away Abode.- Review Count: 5, Rating: 9.6

Accommodations in Historic-District that serve free breakfast include:

  • Flag House Inn.- Review Count: 29, Rating: 8.9
  • Flag House Inn.- Review Count: 78, Rating: 9.4
  • Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!.- Review Count: 9, Rating: 9.6

Accommodations in Historic-District that offer on-site parking include:

  • Flag House Inn.- Review Count: 29, Rating: 8.9
  • Flag House Inn.- Review Count: 78, Rating: 9.4
  • Stunning Waterfront Cottage with Breathtaking Views!.- Review Count: 219, Rating: 10.0

Some of the best Accommodations in Historic-District are:

  • Flag House Inn.- Review Count: 29, Rating: 8.9
  • COZY DOWNTOWN APARTMENT-Naval Academy Vicinity.- Review Count: 12, Rating: 9.3
  • Annapolis Vacation Home 2 Mi to Quiet Waters Park.- Review Count: 12, Rating: 9.0

Some of the popular Accommodations in Historic-District are:

  • Inn on Main Annapolis.- Review Count: 316, Rating: 8.3
  • Stunning Waterfront Cottage with Breathtaking Views!.- Review Count: 219, Rating: 10.0
  • A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!.- Review Count: 170, Rating: 10.0