Best Vacation Rentals in Chestertown

Brampton 1860 in Chestertown provides adults-only accommodations with a garden and a shared lounge. There's a sun terrace and guests can make use of free Wifi, free private parking, and an electric vehicle charging station. At the bed and breakfast, some units have a private entrance, dining area, fireplace, and microwave. All rooms are equipped with a private bathroom with a hair dryer, while selected rooms come with a fully equipped kitchen with a fridge. À la carte and American breakfast options with warm dishes, fruit, and juice are available. There is an on-site snack bar. Guests at the bed and breakfast will be able to enjoy activities in and around Chestertown, like walking tours. The bed and breakfast also offers outdoor fireplace and a picnic area for a day outdoors. New Castle Airport is 48 miles away.

- "Warm, great staff and loved having squeaky vist whenever we were outside." - "You'll love it here!" - "Pleasant, peaceful and calming."

While you're here, you can enjoy all the comforts of home and more, including a fenced pool and free WiFi, as well as a flat-screen TV and an outdoor entertainment area. Other amenities include laundry facilities, towels, a picnic area, and firewood.

- "Wonderful weekend on a girls trip, rooms were clean with great ac! We loved Michelle at the pool bar, she makes delicious frozen drinks! All of our food was delicious at the restaurant too. Not crowded and all staff was extremely nice!" - "The Marina and taking a walk along the Chesepeake Bay seeking bay glass " - "Stay was great. Loved the bands and bars. It would be nice if we didn’t have to drive 10 miles for breakfast. Eric is fantastic. Did not know golf was free. ( next time will bring clubs)Is there a website? We got all info from Hotels.com. All staff were extremely friendly and helpful. "

Chestertown Family Hideaway with Kayaks and Deck! is located in Rock Hall. This holiday home provides air-conditioned accommodation with free WiFi. The holiday home comes with 4 bedrooms, a flat-screen TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, a microwave, a washing machine, a fridge and an oven. Towels and bed linen are featured. The nearest airport is New Castle Airport, 93 km from the holiday home.

Parking • Pet Friendly • Child Friendly • Laundry • Internet • Wheelchair Accessible

Hotel with free breakfast, near Washington College
A fitness center, coffee/tea in a common area, and a seasonal outdoor pool are available at this smoke-free hotel. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a business center, a meeting room, and laundry facilities are onsite.
Comfort Inn & Suites Chestertown offers 81 accommodations with coffee/tea makers and designer toiletries. 42-inch flat-screen televisions come with premium satellite channels. Refrigerators and microwaves are provided. Bathrooms include bathtubs or showers with hydromassage showerheads, complimentary toiletries, and hair dryers.

This Chestertown hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Housekeeping is provided daily.

- "My husband and I stayed here to celebrate his 50th birthday, and to have a weekend away. . Very clean, quiet hallways, very nice staff. Our only complaint and it honestly didn’t effect our stay is that our room smelled musty. The room was very clean and nice otherwise." - "This stay was much better than my last stay. I appreciate the attention to detail in the cleanliness of the room. Great job!" - "1. Everything I need in the same place. Security and comfort for me and my family. "

Free Wifi is available throughout the property and private parking is available on site. The air-conditioned vacation home is composed of 4 separate bedrooms, 3 living rooms, a fully equipped kitchen with a toaster and kitchenware, and 5 bathrooms. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. Guests can enjoy the outdoor swimming pool at Pet-Friendly Home on Chester River with Dock!. New Castle Airport is 48 miles from the property.

Parking • Pet Friendly • Guest Services • Accessibility • Sports/Activities • Child Friendly • Security/Safety • Pool • Internet • Other

Hotel in Chestertown with free parking
This hotel features coffee/tea in a common area, laundry facilities, and a 24-hour front desk. Free WiFi in public areas and free self parking are also provided. Additionally, free newspapers, a lobby fireplace, and a vending machine are onsite.
Change of towels is available on request.
Red Roof Inn & Suites Chestertown offers 53 air-conditioned accommodations with coffee/tea makers and hair dryers. 43-inch flat-screen televisions come with premium cable channels and pay movies.

This Chestertown hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and desk chairs; local and long-distance calls are complimentary (restrictions may apply). Additionally, rooms include irons/ironing boards and complimentary toiletries. Change of towels and change of bedsheets can be requested. Housekeeping is provided daily.

- "Front desk staff was very helpful and friendly. Check in was quick and without a hitch. Doing some renovations but is fine for a stay " - "thanks" - "Staff were very kind. Easy parking and comfortable rooms." - "nice hotel. helpful staff. stores and dining are walkable distances." - "Person checking me in was not very cordial; Other staff folks were pleasant; nice to have daily housekeeping; sign for motel was not visible (actually went to the next door motel); room size was excellent; hall carpet needs replacing"

Located in Chestertown, Comfort Inn & Suites Chestertown offers 2-star accommodations with a seasonal outdoor swimming pool, a fitness center and a shared lounge. The property has luggage storage space and free WiFi throughout the property. At the hotel, the rooms are equipped with a desk. All rooms will provide guests with a fridge. Buffet and American breakfast options are available at Comfort Inn & Suites Chestertown. Speaking English and Spanish, staff are always on hand to help at the 24-hour front desk. New Castle Airport is 46 miles from the property.

- "Latoya was especially helpful" - "Nice clean comfortable" - "I stay here every time I come and visit my mother. Always great service. Great location and easy in" - "Pleasantly surprised by the upgrades made on the rooms" - "Front desk staff were super kind." - "Comfortable and close to mall with pizza" - "One stay here is enough we will look for other alternatives in the area with more welcoming fair policies to all not jus"

Motel in Chestertown with free parking
Along with a 24-hour front desk, this motel has express check-in and express check-out. Free WiFi in public areas and free self parking are also provided.
Driftwood Inn offers 28 accommodations with coffee/tea makers and hair dryers. Premium satellite television is provided. Guests can make use of the in-room refrigerators and microwaves. Bathrooms include bathtubs or showers and complimentary toiletries.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Housekeeping is provided daily.

- "May was very pleasant and helpful. Will certainly return when we are in the area" - "Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip" - "Mrs Mae is very friendly and helpful. Checks on you to make sure everything is ok. I’d recommend it - stayed 3 weeks for work. Loved my little room!! Mrs Mae was a bonus!! " - "I decided to go low-budget for my two-night stay in Chestertown (in town for the Rock Hall Triathlons). This place is convenient and an excellent choice for someone who doesn't plan to spend a lot of time in their room. Rooms are spare w/no frills. Basically four lights in the entire room (overhead, wall, bathroom, shower). Bed was reasonably comfortable. I did notice that the shower temperature control looked a little grungy on the inside; otherwise, the room was clean and fit for purpose. I would stay here again if I were seeking to economize."

This motel is located just a 6-minute walk from Washington College. It offers free Wi-Fi and a 24-hour front desk. Downtown Chestertown, Maryland is 2 miles from the motel. The Driftwood Inn has rooms decorated in rustic wood paneling and soft neutral colors. All rooms include a cable TV with HBO channels, a microwave, and refrigerator. Coffee is provided in the lobby and vending machines with drinks are available. The Inn Driftwood also provides copy and fax services at the front desk. Chester River Yacht and Country Club is 2.5 miles away from the Driftwood. Remington Farms National Wildlife Preserve is a 14-minute drive.

- "No frills, gets the job done" - "I will stay again."

Relax on the scenic Eastern Shore. We are located just off the Chester River. Step away from the hustle and bustle to our cozy cottage appointed with modern amenities. Our property is enjoyed my families and friends.
Our tranquil backyard offers a fire pit and picnic table for entertaining
We have bikes and kayaks for guests to enjoy while they unwind

15 mins from Washington College

The main floor includes a spacious living room, dining room and kitchen.
The second floor offers (2) spacious bedrooms with a loft that includes the bunk beds.
Outside has a spacious deck with a picnic table and grill that overlooks a patio with a fire pit for guests to enjoy in the evenings.
Additional entertainment amenities include (2) kayaks, (2) bikes, horse shoes, and fishing poles.

Guests utilize self check in to access the cottage.
The barn stores the additional amenties (kayaks, fishing poles, bikes and fire wood) for safe keeping and easy access.
Minutes down the road you have access to the Chester River and can spend the day paddling with our kayaks

Self check in for guests. Hosts are available as needed by guests. We are here to help, but not intrude on your trip!

Relaxed riverside community

- "Location is very quiet and tranquil. "

Offering a garden, Carriage House Hideaway In Center of Chestertown offers accommodations in Chestertown. The accommodation is non-smoking. New Castle Airport is 48 miles away.

- "Perfect place for a weekend stay" - "To short, definitely need more than one night to enjoy this gem"

The privacy of a waterfront home welcomes you to pause and enjoy the beauty of the Chester River. Water views from every window connects you to the flowing water and the expansive outdoors. The southern exposure welcomes spectacular sunrises and sunsets. Relaxation and inspiration is abundant in this buffer zone!

Located close to both Chestertown and Rock Hall, it is an ideal gathering space for families and friends with many activities available in the area. By boat, this energetic space is located near Comegy Byte, the Langford Creek and the Corsica River. There is a boat launch within 1/4 mile of the house and a boat slip at the house; water depth is 2.5 feet MLT. Fishing from the 70 ' dock does not require a license.

For outside gathering, there is a large deck by the water with tables for dining, a picnic table under the shade of a holly tree and a water view bistro table and pergola beside the house.

For cooking, you can enjoy our amazing chef's kitchen with single oven, dishwasher, and fully stocked with dishes and utensils, including toaster and coffee/tea bar. You can also cook outside on our gas grill or charcoal grill. If dining inside, you can entertain guests at our kitchen table/dining bar or enjoy the water views at our second dining table.

For relaxation and amenities, we have a fantastic living room and dining area with water views, full size washer and dryer, 2 TVs with Direct TV, high speed internet, books, games and more! We also have an outdoor fire pit and indoor fireplace for entertaining. Firewood is available for your use.

We provide kayaks and paddle boards for you to enjoy the water around the property. We also have bicycles for you to explore the surrounding landscape. A few crab pots are available to try your luck for the famous Maryland blue crab. Bring your own fishing gear to fish directly from our private pier!

Three large bedrooms. Entry level bedroom has a king bed with two single day beds. En suite bathroom with shower and soaking tub. Perfect for families with smaller children.

The second bedroom has a king bed and the third bedroom is a queen. Both have chairs for reading and large closets. One hall bathroom has full bath while the other contains a shower stall. Linens (bed sheets, bath towels and hand towels) are provided with the rental contract. Please contact us if you are interested in opting out of the linen rental during your stay.

Come and fall in love with this retreat; return often!

Keywords: Self-catering, one-story water front cottage

- "Beautifully appointed home - clearly the owners care very much about their property. Tastefully decorated. Everything is in tip top shape - inside and out. Super clean. Nothing is lacking - everything you need is here. Jared - the property manager - is very responsive. Peaceful, quiet neighborhood. Thoroughly enjoyed our stay. Thank you!" - "This is our fourth time staying at Cliff Point and we can’t wait to come back. We enjoyed the beautiful sunrises and sunsets, and how comfortable we feel in this home."

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped with a queen sized bed, linens, washer/dryer, microwave, refrigerator, dinette, toiletries, lux robes... everything you could possibly need to escape the hustle and bustle of life. An additional sleeper sofa, crib, etc. are available at request. Walk to the waterfront or historic district, ride bikes on back country roads. We are more than happy to help arrange paddleboard and kayak adventures! *We require guests to have a verified profile by VRBO OR verification by ID prior to stay*

- "Very quiet location and nice room. Plenty of room. Would have liked a regular coffee maker. And a softer chair to sit on." - "Only stayed for one night but would definitely enjoy more. Amazing family with hospitality that went above and beyond.. Close to town and a nice escape." - "Clean bedroom with bathroom and washer/dryer to stay in while visiting family in the area. The neighborhood is quiet. Our privacy was respected. Owners were available to address our questions. We hope to meet them when we visit again. Linda and Dave"

Escape to a secluded, romantic studio getaway in the middle of Chestertown. Private parking, and over an acre of gardens to call your own. Totally private with views of nature all around, this is the perfect place to relax in front of the fireplace. (Electric, but very cozy and realistic.)
Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and coffee maker.
Comfortable queen bed, kitchenette, and washer dryer.

- "Second stay here this year. It’s becoming our eastern shore home away from home." - "Wonderful place for my wife and I visiting our son at Washington College" - "Just what we needed..." - "A cute studio that had everything, plus walking distance to historic and shopping areas. I would stay there again!" - "Very cozy upstairs studio just off High Street. Well appointed and stocked. I highly recommend it." - "Close to town, easy to get to, clean and tastefully appointed suite, awesome hosts. It truly does not get any better than this!!"

Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining room, Deck, not to mention from the 'L' head on the dock. All the other rooms enjoy a view of a large pond where you can watch Osprey, Eagles & Heron enjoy the fishing site. Most evenings you can listen to the Bull frogs sing. There are 3 large bedrooms (3 queen beds + 2 twins.) Each bedroom has smart TVs. Two have views of the river & the other has views of the large pond out front. The family room features a queen sleeper sofa with air mattress & has a view of the river. The family room features hardwood flooring, wet bar w/wine frig, recessed lighting, smart TV, and decorative fireplace. The kitchen & dining area feature an open floor plan with ceramic tile flooring, cherry cabinetry, granite counter tops, & a raised bar between the kitchen & dining area. There are double pocket doors into the family room for privacy. There are sliding glass doors from the dining area that will go out to a large deck that has a cushion patio set & umbrella. There is a laundry area that includes a stacked washer & dryer. All bathrooms have been renovated. There is a full living room with a view of a large pond. Plenty of parking, a small beach, 50' dock w/10X20 'L' head to relax & watch the sunrise or fish/crab. Bar-B-Que grill, (propane) as well as plenty of Adirondack chairs. Kayaks & paddle boat & boards are available (pls note, although there are 4 adults life vests, we do not supply children's life vests. Although, we have young grandchildren & as long as they are not in use, feel free to borrow.) There is also a fire pit for those cool nights or to just hang out and make smoors. High speed internet added in 2021 NEW for 2022! The interior and exterior have been freshly painted. New siding and new living room furniture, new patio cushions, 6 smart tv's & ceiling fans. New for 2025! upstairs bedroom with walk in closet and private bath. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover Track. We are also 25 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown.
** Some dates to consider for fun filled family weeks.
Chestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Sept
Sunday on 4th of July weekends is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times. This whole area is loaded with festivals. Here's a few more.
Bettertown days @ Betterton Beach usually the fist weekend in Aug
The second weekend in Aug is pirate's weekend in Rock Hall another great time to be had. Lots of people dress up for the event. In Chestertown, Sultana down rigging late Oct early Nov, early Dec is Dicken's weekend & early Oct is Rock Hall's Fallfest.
Every Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town. 3rd Thurs 6-8 pm is cars on high April thru Oct.
Wilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know.
Feel free to surf the web as well. Most of the local towns have event calendars you can find online.
Special winter monthly rentals available (rate does not include utilities for stays exceeding 30 days.) Please be aware, that there are no fences. Neighbor has two dogs that are very friendly and may come over to greet you.
FYI, the school zone has camera 24/7, so watch your speed.

- "We really enjoyed our short visit at your rental home. It was very clean and comfortable and provided everything we needed. We liked it so much we hope to return next year for a longer visit! Thank you for your hospitality. " - "Our stay on the Chester River was great. We had plenty of room for four of us. The accommodations were clean and well appointed. We loved sitting out at the end of the dock and even put a fishing line in the water. The house is very secluded but only a few minutes away from Chestertown and any of the shopping we needed. We would go back again. "

Beautiful1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic Chestertown has to offer as the house is walking distance to the shops, restaurants, Chester River Waterfront, and year round Saturday farmers market. Located on a one way street that is flanked with beautiful historic homes and free on street parking. For those with boats, the home is a short walk to the Chestertown Marina which has a boat ramp and transient slips. Our home is only 2.6 miles from Brittland Manor. Please note there is a ring camera by the front door for security purposes.

- "The property is charming, clean, well-equipped, and located steps to the farmers' market and downtown shops. We would definitely stay again." - "What a wonderful vrbo. Centrally located, charming historic home that was renovated. Really felt like “home”. So much so that the family decided that we’d like to make it an annual tradition" - "This home was nicely decorated with everything well thought out by the owner. Well appointed and clean design aesthetic. Loved the walk in closet; don’t even have that at home. Great to be able to walk to the small downtown area. Very welcoming. Would definitely rent again."

Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath.
Our house is in the historic district of Chestertown, and a two block walk from both Washington College and the Chestertown waterfront. It features two master bedroom suites, one on the ground floor. There are three more bedrooms and a secluded yard. Just outside your garden gate is over an acre of manicured gardens to explore. Gas grill on patio

Over the years, we have stayed in a lot of vacation rentals, and we know what we need as guests.

1. Comfortable beds and furniture
2. Quality linens and towels
3. Limitless hot water
4. Well-equipped kitchen (hate buying
corkscrews!)
5. Peace and privacy, but security in knowing
someone is always available.
6. CLEAN, CLEAN, CLEAN.

Our goal is to give you the experience we would want to have. To maintain quality control we do our own cleaning, and we are available 24/7 if you should need anything, but will be invisible otherwise.
The entire house and fenced yard is yours, as well as the large gardens, which are right outside the back gate. We might be doing some gardening in the large garden, but will keep our distance.

- "Home is meticulously maintained, located on a quiet cut de sac. Walking distance to the restaurants and shops on Main St. Wonderful amenities -- coffee bar, bottled water, etc." - "We were a group of family and friends in Chestertown for a week. Bob and Beth have a beautiful, comfortable house, and there was plenty of room for the seven of us. The house was very clean. The kitchen is equipped with everything you need to have a nice dinner at home. We liked the wine refrigerator, too. We will definitely stay at this property again."

Escape to tranquility at Mill Creek House, a contemporary waterfront sanctuary just 15 mins from Chestertown. Enjoy sunset views from the private dock, watch wildlife, and explore the creek with kayaks. Modern amenities like central AC, WiFi, and a gas grill ensure a comfortable stay.

Nestled in nature's embrace, our cozy house offers a serene retreat with breathtaking views and abundant wildlife. As you step onto the property, you'll be greeted by the tranquil sight of the water gently lapping against the dock.

With two bedrooms and 1.5 bathrooms, our home provides a perfect balance of comfort and intimacy. Every room boasts stunning water vistas, ensuring that you're never far from the beauty of nature. Whether you're sipping your morning coffee in the kitchen or lounging in the living room, the panoramic windows allow you to immerse yourself in the natural splendor surrounding the property.

Outside, the land across from our dock is conserved, preserving pristine scenery that's second to none. You'll often spot bald eagles soaring overhead, a testament to the unspoiled wilderness that surrounds us.

For those seeking adventure on the water, we provide four kayaks for guest use. Explore the tranquil creek, meandering through lush marshlands teeming with life. While the water off the dock may be shallow depending on the tide, kayaking towards the bay offers the perfect opportunity for swimming in deeper waters.

Fishing enthusiasts will delight in the abundance of marine life right at their fingertips. Cast your line off the dock and reel in a variety of species, from rockfish to catfish and white perch. Keep an eye out for ospreys and eagles, ever vigilant as they dive for their next meal, a testament to the rich ecosystem thriving in the area.

Recently dredged, our creek now boasts a channel with a depth of 5 feet, including the spur off the dock, ensuring easy access for boating enthusiasts. Whether you're seeking relaxation or adventure, our waterfront retreat promises an unforgettable experience immersed in the wonders of nature.

- "The home is perfectly located to experience nature on the waterfront with wonderful views. The home is fully equipped with everything and very comfortable. Our couple of friends from France truly enjoyed the espresso machine. We all enjoyed kayaking and fishing. We absolutely recommend anyone who loves nature to stay here." - "It was super peaceful and relaxing. We fished and read and spent the week decompressing and absolutely loved the area!"

Welcome to Eagle Point Farm located on Maryland's beautiful Eastern Shore, a 90 minute drive from Washington DC, Philadelphia or Baltimore. Experience the beauty of the Chester River from this secluded farm located minutes from historic Chestertown, Washington College and the new Kent County YMCA.

Our 350-acre working farm sits on the Chester River and features a private forty-foot pool, a sport court (equipped for tennis, basketball, and pickleball), waterfront access and high-speed internet. There is easy access to fishing in the pond or on the river and kayaking, canoeing or paddle boarding from the private dock.

Resident wildlife includes Bald Eagles, Osprey, Deer, Fox, Migrating Water Fowl of all types and Wild Turkeys. Bring your bike and enjoy Kent County's beautiful, flat country roads. Watch the sunset from the deck or screen porch overlooking the pool, pond, river and corn fields. On cooler days, there are two wood burning fireplaces and a fire pit to gather around.

Historic Chestertown offers restaurants, shops, and a wonderful farmer's market on Saturday mornings. Groceries can be delivered from the local Acme grocery store via Instacart. Local restaurants offer both outdoor dining and takeout options.

Our tastefully decorated home offers four bedrooms with ensuite bathrooms. Three bedrooms have queen beds and one bedroom has two twin beds. We have three desks in the house to facilitate work from home -- one in the main bedroom, one in a queen guest bedroom and one in the kitchen. The main bedroom also has a wood burning fireplace. We provide linens and towels. The upstairs great room, leading to a deck and screened porch, offers spectacular river and farm views and a cozy first floor den provides a second gathering space. The dining room seats eight comfortably and the spacious well outfitted kitchen makes it easy to cook for a crowd. The kitchen is fully equipped including a desk and printer, which when coupled with high-speed internet provides an ideal work from home / remote work environment. We welcome families and pets. We ask only that you treat our house as you would your own.

Property Information & Notes:
o Swimming Pool: Please note our swimming pool is open from May 1-October 1.
o Acreage: 350 +/- acres of complete privacy though the farmer may be working in the fields .
o Fireplaces: 2 Wood Burning Fireplace Ample Firewood on site
o Firepit
o WiFi: High speed internet (up to 1 Gigabit down and up) provided via Talkie.
o Pet Policy: This property is dog-friendly for up to two dogs at an additional charge.
o Grill: This property has a propane grill. Propane is provided.
o Fully equipped Gourmet Kitchen
o Screened Porch
o Outdoor dining
o Walking / Running Trails
o Bass Pond

Keywords: Escape, Privacy, Farm, Eastern Shore, Waterfront House, Chester River, Chestertown, Maryland, Country, Wildlife, Secluded, Pool, Dock, Sport Court, Pickleball, Washington College, Fishing, Maryland Crabs, Rock Hall, Chesapeake Bay, WIFI, High Speed Internet Access, Tastefully Decorated, Social Distance, Remote Work, Work From Home, Desk. Monitors, House, private pool, pickleball

- "I am so grateful to have had the opportunity to experience this place! Beth couldn’t have been more helpful and accommodating! The property is a gem…wide open with a perfect view of the river, yet private! It’s a nature lovers dream. I was impressed by the native landscape and conservation efforts. I think there is a lot of history here and I feel so fortunate we were able to experience this special place! And the beds were SO comfortable!!!!"

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!

Our guesthouse is a two-floor 525 sqft unit with a queen bedroom and en suite bathroom upstairs, and a living room with dining/working area and kitchenette downstairs. You'll love the private patio space, which offers separate seating and dining areas with beautiful views of our garden and access to the fully-fenced backyard and grill.

We are proud to give back to our town through the renting of our guesthouse. Five percent of our gross revenue is donated to one or more local non-profits annually. Additionally, the guesthouse features artwork from local artists and galleries, and you'll find home goods and products from nearby shops.

Our place is designed to provide you with everything you need for a comfortable stay, including fast wifi, a private entrance with self check-in via keyless entry, and free street or off-street parking.

You'll find all the essentials like towels, bed sheets, soap, and toilet paper, as well as a hairdryer, cleaning products, shampoo, conditioner, and body soap. There are extra pillows and blankets, and hangers to store your clothes.

The guesthouse has two brand new air conditioning and heating units that you control, so you will be comfortable year-round.

Safety is a top priority, so we have a smoke and carbon monoxide alarm, a fire extinguisher, and a first aid kit on hand. Additionally, for awareness, there is a Ring Video Doorbell installed on the front door of the primary house. It is used to monitor our front door but not the door of the guest unit.

In the kitchenette, you'll find a microwave, dishes, silverware, cups, a mini-fridge with freezer, a hot water kettle, a coffee maker (both a Keurig and a Nespresso), wine glasses, and a toaster.

During your stay you will have exclusive access to the following rooms and spaces:

- Bedroom
- Full bathroom
- Kitchenette
- Living room
- Dining area
- Patio

Additionally, you'll be sharing the backyard with us, but we'll do our best to give you privacy during your stay.

If you have any questions or concerns about the areas you can access, or if you need any additional information about your stay, please don't hesitate to ask.

We're committed to providing our guests with an exceptional experience, and we're always available to answer any questions or provide recommendations to help make your stay unforgettable.

Here's what some of our recent guests have said about their stay:

"Perfect apartment-type accommodation located in a lovely walkable town. These hosts literally thought of a guest's every need... Besides being a comfortable, beautiful space top to bottom with an abundance of windows, the things that really stood out for us are: Self-check in keyless entry, gallery artwork throughout; large stone-top table with chairs for eating, gathering, working, etc; coffee machine with Keurig AND Nespresso pods (WOW!)" - Cindy

"Their place was exactly what I was looking for! It was clean, cute, centrally located, but yet private and offered everything I needed for my stay! I loved the special touches from the local businesses, the espressos, coffee, and tea options. Their place was spotless and the bed was extremely comfortable! They were also very responsive with any questions I had. If I ever come back to the area I will definitely stay at their place." - Megan

"Great place and location. Private and quiet, but walkable to restaurants of Chestertown. Comfortable and super clean! Very cute, indoors and out." - Joan

"Stephen and Marianna were delightful hosts for a perfect getaway weekend in Chestertown! Their detailed suggestions of local restaurants and events made our stay more enjoyable, as were their thoughtful messages to us during our stay to ensure that everything was going well. The apartment is such a gem tucked away in a courtyard at the back of their house in the historical section of town!" - Carla

We're confident that you'll love your stay at our guesthouse, and we can't wait to welcome you.

Book now to secure your spot!

- "Beautiful space… Artfully decorated… Super comfy bed… super convenient location… Lots of nice little extras, like coffee maker, mini fridge, plates, cups, utensils… Beautiful outdoor courtyard, with a nice little space to have a cup of coffee or a glass of wine! Hosts are a great couple- very attentive and responsive…. Hope to be back and stay here again…. highly recommend!" - "We had a very enjoyable weekend at this property. The owners were super friendly and helpful! We would definitely stay here again when visiting the area."