Charming Guest Houses in Annapolis, MD

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.

- "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."

Bed & breakfast in Annapolis with free breakfast
A snack bar/deli, WiFi in public areas, and conference space are available at this smoke-free bed & breakfast. Self parking is free. Other amenities include concierge services, an arcade/game room, and wedding services.
Laurel Grove Inn on the South offers 5 accommodations. Housekeeping is provided daily.

- "It was a short stay. We are local and wanted a nice place to stay while we were having noisy plumbing repairs done at home. Tiffany, the inn keeper, Was very accommodating for my elderly wheelchair-bound mother. Views of the river were beautiful. I look forward to coming sometime when I can stay and perhaps kayak the river." - "Now I understand why the great ratings! What a wonderful place to stay. Beautiful views, comfortable with all the conveniences of home. Great hosts who go above and beyond to ensure your stay is fabulous. We will definitely return!"

White light retreat offers accommodations in Bowie, 10 miles from Supreme Court and 10 miles from Washington Union Station. The air-conditioned accommodation is 5.7 miles from Addison Road-Seat Pleasant, and guests can benefit from private parking available on site and free Wifi. National Museum of the American Indian is 11 miles from the bed and breakfast and Nationals Park is 11 miles away. Towels and bed linen are provided in the bed and breakfast. The accommodation is non-smoking. U.S. Capitol is 10 miles from the bed and breakfast, while National Gallery of Art is 11 miles away. Ronald Reagan Washington National Airport is 17 miles from the property.

Parking • Security/Safety • Air Conditioner • Fireplace/Heating • Internet

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.

- "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. "

Colonial bed & breakfast in Annapolis with free parking
This smoke-free bed & breakfast features a refrigerator in a common area, concierge services, and express check-in. Free WiFi in public areas and free self parking are also provided. Additionally, express check-out, tour/ticket assistance, and a garden are onsite.
Housekeeping is available on request.
Inn at Horn Point offers 3 air-conditioned accommodations with complimentary bottled water and designer toiletries. Each accommodation is individually furnished and decorated. Pillowtop beds feature Egyptian cotton sheets and premium bedding. This Annapolis bed & breakfast provides complimentary wireless Internet access, with a speed of 250+ Mbps (good for 3–5 people or up to 10 devices). Bathrooms include complimentary toiletries and hair dryers. In-room massages, hypo-allergenic bedding, and irons/ironing boards can be requested. Housekeeping is provided daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

- "This B&B was centrally located, clean,safe and quiet. However, even though I knew there would be no breakfast, I thought that like most B&B’s there would be the possibility of coffee or tea in the morning. There was no one home to welcome us or give information about nearby restaurants, etc. Why take the reservation if you can’t provide the amenities most B&B’s feature?" - "Great place in an awesome location. Very friendly staff. Easy street side parking."

Welcome to this beautifully remodeled home! Perfect for large groups and families with kids, this offers a wide array of activities to keep every one entertained. Gather around the fire pit and
enjoy cozy evenings. Unwind with board games indulge in some friendly competition on the air hockey or ping pong table. Take advantage of the exercise equipment.

This home is conveniently located near major cities such as Baltimore, MD, Annapolis, MD, Washington D.C and Northern VA. It offers a separate fully furnished office space for your convenience. The recreational room is equipped with a pull-down screen, a card/bar area complete with a fridge and microwave, a full body gym, air hockey, and ping pong. Enjoy the outdoors in the enclosed porch surrounded by three spacious decks. Take a refreshing dip in the pool or relax in the 6 person hot tub. Complete your evenings with cozy gatherings around the fire pit.

Internet • Balcony/Terrace • Air Conditioner • Other • Guest Services • Laundry • Kitchen • View • Parking • Wellness Facilities • Security/Safety • Child Friendly

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

The space
Kitchen has large sliding picture window with outdoor service shelf to pass food and drinks onto the patio. Full sized fridge with ice maker and plenty of pantry and cabinet space. Two burner induction cooktop. Microwave / Convection Oven. Gas grill outside. Room darkening privacy shades. Appointed with basic cooking and serving tools. Electric griddle. Blender. On demand, continuous hot water heater. Plenty of clothes-hanging and storage space for vacation-length stays. Wall mounted flat screen Smart TV on swivel. WiFi. Two person indoor dinette on wheels. Outdoor dining table. 15,000 BTU HVAC, ceiling fan, whole home circulating fan, and attic exhaust fan. Very well insulated and quiet. Bluetooth speaker. Additional outdoor shower on back of main home available for any who desire to use it. One parking space dedicated to AirBnB guests.

Guest access
In addition to Lil’ House itself - which is totally and privately yours during your stay - the huge bluestone patio, teak furniture, fire pit, and basketball hoop are yours to enjoy. (Note: we will provide some safety guidelines regarding use of the fire pit upon your arrival)

The gas grill on the patio is also for your use but from time to time the owner may also use the grill and will coordinate those brief times with you if possible.

You may also use the traditional picnic table that’s on the backyard lawn.

Finally, there is an outdoor shower attached to the back of the main home that Lil’ House guests may use if so desired.

Other things to note
Bed - as noted in the description, the bed is a queen Murphy bed that can be stowed (raised and stored) away during waking hours and deployed (pulled down) when it’s time to rest. It’s weight-balanced and easy to go from one mode to the other. For those unfamiliar with “Murphy the bed” we are most happy to demonstrate how it works upon your arrival.

Breakfast - just so there are no mistaken visions of gourmet omelets and bananas Foster flambé in bed, please know that our approach to breakfast is to stock your fridge and cabinets with a handful of self-serve continental basics: milk, juice, coffee, cereal, bread, eggs, jam, and maybe bagels and cream cheese or fresh fruit from time to time. We stock these fresh at the start of each new guest stay. If your stay is longer than a week, we will resupply each new week.

Dishwasher - sorry - it’s you 😊. The Lil’ House has a nice big kitchen sink and a drying rack but no dishwashing machine. It’s “glamping” and not camping but think of it as having almost all the comforts of home.

Linens - sheets, towels provided including ready spares and, of course, all are made clean and fresh for the start of each stay. If your stay is more than a week, then we will wash, dry and reset your used linens once each week. If you switch to ready spares during the week, we can likely wash, dry and return to you a fresh back-up set in a day.

Housekeeping - our aim is always to have Lil’ House sanitized, clean and pristine for the start of every stay. If your stay is longer than a week, we’d like to coordinate with you a time for us to do a full reset (cleaning, resupply, fresh linens as needed) once each week while you are sunning on the patio or out on the town.

Registration Details
000111

Cozy, clean one room efficiency located in Edgewater, 15 minutes from downtown Annapolis.

Registration Details
000571

Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapolis, and the Naval Academy. (4.7 miles to the main gate). We are on a private well but we have installed a state of the art water softener, filtration system, and a blue light bacteria zapper.
Home and grounds are kid friendly offering amply outside play space and a multipurpose sports court. Third bedroom of home has a full-sized crib, baby gates, and a twin bed.

The space
Property was totally renovated in 2020 including bathrooms, kitchen, appliances, floors, windows, and HVAC system.

Guest access
Guest have private access to the entire home and yard. There is shared access to the driveway, parking lot, and sports court.

Other things to note
Coffee and filtered water is offered inside of the refrigerator. There are some basic spices in the cabinet above the coffee pot.

Registration Details
135969

Hot water • Cleaning products • Conditioner • Ocean Essentials body soap • Hair dryer • Shower gel • Bay view • Shampoo • Bathtub • Courtyard view

Recently renovated (Feb. 2021) one bedroom Guesthouse with fully equipped kitchen, new king sized bed with premium Saatva mattress, full bathroom and large living room in a quiet neighborhood near the South River, Quiet Waters Park and downtown historic Annapolis.

The space
The Guesthouse is located behind the Main house, accessible from the designated parking area via a bricked path. The Guesthouse is very comfortably furnished. The living room includes bookcases, large leather sofa and a 48" HD TV, DVD/CD player, with a large selection of books, DVDs and CDs. The bedroom includes a king bed, comfortable bedding, built-in wardrobe, and ceiling fan. Bath includes large shower, and a variety of complimentary personal hygiene products may be available for use. Linens and towels are provided. Kitchen includes electric stove and oven, full size refrigerator and freezer, dining table and chairs, toaster oven, blender, microwave and coffee maker and tea pot, as well as a large selection of sauté, baking and sauce pans and other cooking utensils. A variety of sundries, such as coffees and teas, salt, sugar and some canned and frozen goods, may be available. The kitchen opens onto the fenced-in backyard patio, which includes a dining table as well as ample seating and side tables under the trumpet vine and wisteria pergolas. Occupancy is limited to one car and 2 guests. The cottage is not suitable for children under 10.

Guest access
The Guesthouse is separate from the main house, with its own entrance, air conditioning and heating systems. Guests may also access the backyard patio area from the kitchen. There is one dedicated parking space available for guests.

Other things to note
The Guesthouse does not have laundry facilities. Smoking is not allowed in the Guesthouse, and pets are not allowed to stay in the Guesthouse. The Owners have a chicken coop in the backyard, as well as a large, friendly dog that will, on occasion, be in the backyard and patio area. This property is registered with the Anne Arundel County Department of Inspections & Permits (License No. STR 2), and questions regarding this license may be directed to the Department.

Registration Details
000002

Conditioner • Courtyard view • Hot water • Essentials • Pantene shampoo • Body soap • Cleaning products • Hair dryer • Garden view • Shower gel

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

The space
The Space
Garden View offers 750 square feet of living space, including a cozy loft. Enjoy your own private entrance, washer and dryer, water heater, and HVAC system controlled by a Nest thermostat. The only shared utilities are water, electricity, and the backyard.

Our tap water is top-notch—be sure to try it before reaching for bottled water.

The kitchen is stocked with everything you'll need for cooking meals or baking treats like cookies.

We've also added a new air mattress! If you have two kids who want to sleep in the loft, let me know, and I’ll set it up for you.

The large backyard is perfect for games like frisbee or football, and we have a fire pit and propane grill available for your use—just let us know if you'd like to use them.

During the summer, I’m happy to share fresh vegetables and greens for a salad.

Guest access
Our neighborhood, developed in the late 1970s, features properties with at least 1.25 acres of land. Many of our neighbors have lived here for over 30 years. It's a great place for dog walking, jogging, or bike riding, and you're sure to meet some friendly faces.

Registration Details
000304

Free washer – In unit • Garden view • Hot water • Tresemme conditioner • Bathtub • Aveeno body soap • Tresemme shampoo • Hair dryer • Cleaning products • Shower gel

This private treehouse apartment, located above a detached garage, is nestled among the treetops on a wooded acre of land in a friendly, walkable, and quiet neighborhood. The apartment is a beautiful space with modern furniture, vinyl plank floors, a king-size bed, and a 50-inch flat-screen TV. We are located 3 miles from historic downtown Annapolis, the Naval Academy, and the Naval Athletic stadium.

Registration Details
000262

Essentials • Conditioner • Hair dryer • Cleaning products • Hangers • Hot water • Shampoo • Shower gel • Body soap • Bed linens

Private, clean, cozy studio in the heart of Eastport, Annapolis. Quiet, separate, retreat space. Walk 1 block to restaurants and bars in Eastport, hop on the water taxi and you are in the heart of Downtown Annapolis, USNA, and historic areas of Annapolis in minutes. This is an Ideal location for the sailing community or anyone visiting our beautiful city. Free street parking available. You could park your car and never have to move it through out your stay. Walk, bike or water taxi.

The space
Designed by a local architect, this space has unique design features to maximize the use of the space

Guest access
This is a separate studio so you will have the place to yourself. There is a Smart TV, desk, WiFi, mini-fridge, sink, coffee/tea etc for your convenience but no microwave or cooking features which should not be an issue as there are so many fabulous restaurants with in 1-2 block walking distance.

Other things to note
There are people that live on the property full time as well as another Airbnb space that is on the second floor in the back of the main house.

Please be respectful and courteous of the other guests and tenants on the property.

We do encourage you to enjoy the outdoor spaces however the lower back deck on the main house is off limits.

Essentials • Shampoo • Shower gel • Body soap • Hair dryer • Hot water • Hangers • Cleaning products • Garden view • Bed linens

Cozy nautical place,(ENGLISH & FRANCAIS) beach at 4 minutes walk, very nice area in avery quiet neighbourhood.

Registration Details
141959

Shampoo • Essentials • Bed linens • Free dryer – In unit • Hangers • TV • Hair dryer • Hot water • Iron • Free washer – In unit

Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtfully interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

The space
Your home in Annapolis! Barefoot Cottage is a 1-bedroom Airbnb nestled along the tranquil shores of the Chesapeake Bay, perfect for solo quiet retreat, couples retreat, and everyone visiting for any of the fun events happening in and around town. As you step inside, you'll be greeted by a charming interior adorned with coastal decor and soothing hues reminiscent of the nearby waters. The bedroom features a plush queen-sized bed, promising restful nights after days of exploration. The living area offers a choice of comfortable seating areas to unwind with a glass of wine, watch a movie or cozy into the corner lounge chair with a good book. Laundry area is tucked away under handmade live edge wood and epoxy countertop. Whip up a delicious meal in the fully-equipped kitchen, complete with all the essentials for a delightful cooking experience.

With access to a private beach close by, you can spend your days lounging in the sun, enjoying a picnic lunch or strolling along the bay. Feeling outdoorsy? Included with your stay you will find 2 folding bicycles and 2 inflatable paddle boards!

Whether you're seeking relaxation or adventure, our Chesapeake Bay retreat offers the perfect haven for a memorable visit to Annapolis's rich maritime history and vibrant culture.

**There is a steep staircase with 13 stairs leading up to the second floor**

Our cleaners take every precaution when cleaning Barefoot Cottage. All high touch surfaces are thoroughly disinfected (including light switches, knobs, handles, remotes etc.) using Seventh Generation cleaning products. All throw pillows have removable covers and are washed after every guest. All Free and Clear laundry detergent for our towels and bedding which are washed on the Bedding/Hygiene cycle in our HE washer and dryer. Guests have self check-in with no physical interaction with anyone.

SLEEPING ARRANGEMENTS 1BR/1BA/Sleeper Sofa comfortably sleeps 2 adults, 2 adults/2 children or up to 3 adults:

Primary Suite
- Queen Bed
- Sitting Area
- Flat-screen t.v.

Living Room
- Full sleeper sofa
- Flat screen t.v.
- Reading nook

HIGHLIGHTS
Private entrance and parking for one vehicle
High Speed Internet and WI-FI
Full-size washer and dryer
Eat in kitchen
Chesapeake Bay oriented community with private beach and park
Non-smoking
Service animals welcome
No pets
Keyless entry with personal lock code for the duration of your stay.

********************

Distance to local attractions:

Water Taxi - 3 miles

Downtown Annapolis - 4 miles

U.S. Naval Academy - 5 miles

Washington, DC - 35 miles

Baltimore, MD - 20 miles

*******************

House Rules

Check-in 4:00 p.m.
Check-out 10:00 a.m.

Parking for ONE vehicle only!

License Number
000618

Guest access
Guests have full access to every part of the Cottage with the exception of 2 locked closest, one on the first floor and the other inside the bathroom on the 2nd floor. We ask you to respect the owners privacy and not attempt to access either locked closet. Everything else is yours to explore and use!
We have parking for 1 vehicle. We cannot accommodate more than 1 vehicle.

Other things to note
Coming to town for a special occasion? We love helping our guests celebrate! From recommendations to fresh flowers, a favorite treat, or bottle of bubbly! Drop us a note about your stay and we will be happy to help you mark a special occasion.

We love supporting our local Annapolis small businesses and happily recommend everything from good eats, charming attractions, and engaging events!

We encourage our guests to follow along on IG as we show off local Annapolis sights and day trips within the region! If you take pictures during your stay or out and about, kindly tag #staybarefootannapolis

Can't wait to help you have an incredible Annapolis stay!

Registration Details
000618

Hot water • Tresemme shampoo • Free dryer – In unit • Free washer – In unit • Cleaning products • Tresemme conditioner • Shower gel • Bathtub • Dove body soap • Hair dryer

Charming studio guest house in the heart of Eastport, just half a mile from downtown Annapolis and steps away from local dining and shops. Enjoy the convenience of free parking. Ideal for a cozy getaway with easy access to all the best Eastport and Annapolis have to offer.

The space
Location: Nestled in the heart of Eastport, just steps away from beloved dining spots like Boatyard, Adam’s on the 4th, and Carol’s Creek. A short stroll over the Eastport Bridge takes you to Downtown Annapolis, where you’ll find shopping, historic attractions, and waterfront activities.

Studio Layout: This cozy yet spacious studio apartment sits above a garage, offering a private retreat with modern comforts.

Sleeping Arrangements:
- King Bed – Unwind in a plush king-sized bed for a restful night’s sleep.
- Queen Pull-Out Couch – A comfortable sleeper sofa provides additional sleeping space.

Bathroom: Enjoy an updated, modern bathroom stocked with fresh towels and essentials for your convenience.

Kitchen: A fully equipped and spacious kitchen awaits, featuring all necessary appliances, cookware, and utensils—perfect for preparing meals during your stay.

Living Area: Relax in a comfortable space with a TV and an Amazon Fire Stick for streaming your favorite shows and movies.

Laundry: A washer and dryer are available in-unit for added convenience.

Parking: Includes one dedicated parking spot for your stay.



Please note - guests are permitted to use the patio out back but are no longer permitted to use the hot tub.


License Number: RENT-004027-2024

Guest access
Guest house above the garage and the patio directly behind the garage. Guests are no longer permitted to use the hot tub.

Cleaning products • Body soap • Bed linens • Shampoo • Free dryer – In unit • Hot water • Conditioner • Shower gel • Washer • Hangers

VERY CLOSE to island wedding venues. Cottage is a private detached 1st floor dwelling and has off street parking. Queen bed & trundle with 2 single beds, sleeps 4. There's a full/stocked kitchen & bath, large TV, small dining table, Keurig & coffee pods. Wifi and streaming service's included. Easy access with keyless entry. Efficiency space. Smoke/Vape allowed on front porch only.
Located near the Bay bridge and bike paths, Historic downtown, winery & restaurants. *Message with any questions.

The brand varies shampoo • Clothing storage: closet • Hangers • The brand varies body soap • Bed linens • Essentials • Hot water • The brand varies conditioner • Hair dryer • Iron

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

The space
We love to share our property! You should feel comfortable picnicking on the lawn or point. We love it! The studio is a one-room apartment (plus a full bathroom with shower and tub) above a detached garage. The garage is connected to a main house by an open breezeway. Our family of four lives in the main house, and you may see us from time to time (including at the pool), but guests have full use of all the outside areas as well as their own patio and private entrance to the studio. The door to the studio apartment is just inside the garage and opens to the staircase. The TV is a Roku smart TV. You can do Apple share and screen share from your device. The TV has free channels as well as access for Prime, Roku, etc., but guests will need to provide their own log-in for these apps.

The pool area is a wonderful area to relax and unwind. Day and night swimming is welcome. At night the pool lights up and has a spectacular 180-degree view of the Bay. Cushions for the deck chairs are in the large brown bin, and floats are in the shed--help yourselves!
The pool area is located on the other side of the property from the Airbnb studio. It is a 25,000 gallon concrete pool approximately 9 feet deep in the deep end and 4 feet deep in the shallow end. It is not heated. You will likely have the pool to yourself, but our family uses it from time to time so you may see us out there, too. The pool opens mid May and closes mid October.

Pets are welcome in the studio and the pool. but if they are left in the studio alone we ask that they be in an animal crate. Thanks for understanding.

Guest access
There is parking available in the semi-circular driveway that is in front of the house. We are the last house on a dead-end road in a quiet residential neighborhood. There is a neighborhood community area with picnic tables next to our property that people from the neighborhood sometimes visit, and our guests are welcome to use it as well.

We love when guests make themselves at home on the property--have a picnic, lounge by the pool, let your dog run and even swim in the pool! Let us know if you need help with anything, such as the gas fire pit.

At the other end of our road, about a 10-minute walk, there is a small neighborhood beach. The nearest stores and gas stations are at the top of the island, about a 12-minute drive (guests may want to pick up food on their way rather than drive back up the island). The island has two local airports for small aircraft for guests who fly. There is a dedicated, paved bike path that runs the length of the island, and runs south of us to the Romancoke Pier. There is another path that runs east/west across the top of the island. About 5 miles north of us , there is a public beach with a pet-friendly designated area.

Other things to note
Guests can use the garage to store bikes or other items if needed.

The Inn on Main, Annapolis is a 10-room Bed and Breakfast with Downtown Annapolis literally on your doorstep. Located above a staple of Annapolis, world renowned restaurant. All of our newly renovated rooms feature a thoughtful blend of bold fabrics, modern furnishings, eclectic accents and sophisticated amenities. Each offer plush linens, Hulu TV, free Wifi, and more.

The space
Single Private Room with Private Bathroom and marble vanity. 33+ inch wall mounted smart tv with Hulu Live.

Guest access
Front and Rear Entrances with Coded and Keyed locks.

During your stay
Check In and any help you may need during your stay is available downstairs at Chick and Ruth's - ask for the manager on duty.

Hot water • Hair dryer • TV with standard cable • Air conditioning • Extra pillows and blankets • Hangers • Bed linens • Iron • Essentials • Shampoo

The Inn on Main, Annapolis is a 10-room Bed & Breakfast with Downtown Annapolis literally on your doorstep. Located above a staple of Annapolis, world renowned restaurant. All our newly renovated rooms feature a thoughtful blend of bold fabrics, modern furnishings, eclectic accents and sophisticated amenities. Each offer plush linens, Hulu TV, free Wifi, and more.

The space
Single Private Room with Private Bathroom and marble vanity. 33+ inch wall mounted smart tv with Hulu Live.

Guest access
Front and Rear Entrances with Coded and Keyed locks.

During your stay
Check In and any help you may need during your stay is available downstairs at Chick and Ruth's - ask for the manager on duty.

Bed linens • TV with standard cable • Hot water • Lock on bedroom door • Shampoo • Essentials • Air conditioning • Heating • Hangers • Hair dryer

A bottle of wine welcomes you to this private, architect designed apartment above a newly built detached garage. Enjoy this cozy space with all the comforts of home. We are located on an acre of land in a friendly, walkable neighborhood. The apartment is a beautiful space with modern furniture , hardwood floors, gas fireplace and a 60 inch flatscreen TV. We are located 3 miles from historic downtown Annapolis and the Naval Academy We are 1.5 miles from the Naval Academy Stadium.

The space
The kitchen is equipped with a Nespresso coffee maker and pods, microwave, toaster and refrigerator. We have Netflix, Amazon prime and cable tv available for your use.

Guest access
The main garage is a shared space with a 65 inch TV , max trainer, workout mat and weights for guest use.

Registration Details
000162

Safe • Bed linens • Hot water • Hangers • Hair dryer • Conditioner • Iron • Essentials • Extra pillows and blankets • Shampoo

Experience a one of a kind waterside getaway in our historic Boathouse on the Chesapeake Bay! Beauty and serenity abound just minutes from downtown Annapolis by both land and sea. Watch the sunrise from your bed as the birds soar overhead. You can hear the water gently lapping all around you. Guests can enjoy our Paddleboards and Kayaks. Bring your own boat or water toys to tie up to the pier. Crabbing & fishing are right outside the door.

Registration Details
000362

Gorgeously constructed and furnished 2 bedroom private guest home in Eastport. Enjoy all our favorite bars and restaurants that Eastport has to offer while also being only 1 mile from Downtown Annapolis! A quick walk downtown.

The space
Walk into the gorgeous 2 story vaulted open floor plan! This light filled space includes a gorgeous kitchenette, built in breakfast nook, a queen sized pull out couch and a 55" smart television. The designer kitchenette includes a sink, dishwasher, full size fridge/freezer, microwave, coffee maker and air fryer/toaster oven. Please note there is no stove/oven.

The second story includes 2 bedrooms each with a queen bed. The shared bathroom includes a marble top double vanity and tiled shower w/tub. There is also a front loading washer and dryer upstairs!

The paver patio includes a gorgeous dining space.

Guest access
A smart lock allows for guests to access the unit independently! No need for scheduling arrival or departures.

Other things to note
No pets allowed.
There are steps inside as well as outside of the unit!
Public street parking.

Body soap • Bathtub • Clothing storage: closet • Bed linens • Conditioner • Free dryer – In unit • Hot water • Hangers • Free washer – In unit • Shampoo

Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, including spectacular sunrises and fishing off the pier (rockfish are very abundant). Perfect for families, couples, or friend groups who are looking to get away from it all.

If you are traveling with small children, we have high chairs and a pack and play available upon request.

Recent June 2022 updates include new memory foam mattresses, new outdoor lounge chairs, and Roku.

The space
There are two bedrooms, one bathroom, a spacious living room (includes pullout couch), kitchen, and a large deck looking towards the water.

There is plenty of yard space for outdoor games. If you like water sports, fishing, outdoor games, or just a romantic weekend on the water, the property has a 250 foot long pier with underwater fishing lights at the end. Love Point is where you want to be!

Guest access
Entire cottage, entire cottage patio, entire yard, entire pier

Other things to note
- Pier (shared with the main house located on the same property)
- Dock (with accommodations from owner)
- Boat ramp that is perfect for fishing (underwater light at end of pier to attract rockfish at night), and crabbing.
- Nearby we have golfing, bird & wildlife watching, winery/vineyard, restaurants, shopping, horseback riding, nightlife, museums, and sightseeing.
-Garage is not included in the rental

Riverview Retreat on Warehouse Creek is a renovated, cozy, and luxurious guest house, offering families and groups a serene winter waterfront escape. This private basement apartment, accessible via a separate entrance, features two bedrooms, three comfy beds, and a well-equipped kitchen with top-tier appliances. Guests can enjoy our private dock and boathouse, providing direct access to Warehouse Creek for winter kayaking, paddling, fishing, and seasonal boating adventures!

The space
As you step into the in-law suite, you’ll be welcomed by a bright and inviting open-concept living and dining area. The spacious living room features a large white sectional, perfectly positioned next to a cozy pellet stove, with a TV mounted above—making it the ideal spot for relaxing evenings with a glass of wine. This area is designed for everyone to gather and unwind together. Just to the left of the front door, you’ll find a little sitting nook with a sliding closet, perfect for taking off coats and shoes. Nearby, a table is stocked with complimentary snacks, water bottles, and our welcome guide—a thoughtful touch from the homeowner to help you settle in and get acquainted with the area.

Continuing down the hallway, you’ll find two comfortable Queen bedrooms. One of the Queen bedrooms features two Queen beds, making it a great option for those traveling with family or friends. The other bedroom offers a peaceful retreat with a single Queen bed. The bathroom is conveniently located down the hall, separate from the bedrooms. The fully equipped kitchen also features a washer and dryer, adding extra convenience for longer stays.

When you're ready to enjoy the outdoors, step outside and follow the stone path leading to a stairway that takes you down to the water. Here, you’ll have access to the dock, along with kayaks, paddle boards, and a boathouse that’s perfect for sunbathing or simply relaxing and taking in the tranquil surroundings.

You are welcome to dock their boat at the pier. Use of the nearby boat ramp is also permitted at no additional cost. The water depth is typically around 6 feet.

Guest access
After you park you will follow the winding square tile path down to the waterfront side of the back of the house and enter our inlaw-suite via a private patio. Just enter the door code provided prior to your arrival. You are the only one with access to this space during your stay.

Other things to note
This is an entire private basement apartment with a private entrance, but the driveway and outdoor spaces are shared.

Since this is a shared building, though your space is private, the homeowner asks that you abstain from cooking with distinct spices like curry or strong smelling seafood and fish. If you are unsure, don’t hesitate to ask!

** OUT ON THE WATER INFORMATION**
The homeowner has 3 single kayaks, 1 double kayak, and 4 paddle boards available for your enjoyment during your stay.

Please shoot the homeowner a text or call when you're ready to hit the water. He'll be happy to guide you to where the life jackets, paddles, and other gear are kept. His phone number will be in the Welcome Guide Binder when you arrive at the home.

Early Check-In & Late Check-Out Policy
We offer early check-in and late check-out upon request, subject to availability.
One hour is complimentary
However, a fee applies as follows:
• Early Check-In before 3pm for an additional fee of $50 to be paid before check -in
• Late Check-Out after 12pm for an additional fee of $50 to be paid before check-out
Please request in advance so we can confirm availability. Thank you!

Registration Details
024023

Body soap • Free dryer – In unit • Shampoo • Free washer – In unit • Conditioner • Bathtub • Cleaning products • Essentials • Hot water • Hair dryer

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Guest access
Guests will have full access to the cottage and the outdoor space of the cottage.

Registration Details
000440

Conditioner • Body soap • Shampoo • Bay view • Free washer – In unit • Hot water • Free dryer – In unit • Essentials • Cleaning products • Hair dryer

KING SUITE w sitting room and waterfront patio

Located on the first floor, this King suite features high ceilings and traditional wood shutters welcoming the morning sun. The private bath with a sleek walk-in shower promises a refreshing start to your day. Room amenities include a king bed, a commanding walnut armoire and a waterfront sitting room with wood burning fireplace. Wrap yourself in the luxury and tranquility. (525 sq ft)

KING SUITE w sitting room and waterfront balcony

A lavish second-floor haven, this King suite boasts a private spa-like bathroom with double sinks, a jacuzzi soaking tub, separate shower, and water closet. A walk-in closet, TV, and a private sitting room with workspace add convenience. Take in the Bay breezes and stunning views from the waterfront balcony. Enjoy the refined comfort and style. (840 sq ft)

Hair dryer • Bay view • Scenic views • Hot water • Conditioner • Body soap • Bathtub • Shampoo • Bathroom • Cleaning products