Chestertown is located on the eastern side of Maryland. It got its name from Chester River, which straddles its southeastern side. Colonial inspired architecture adorns most of its streets and has attracted thousands of visitors. Art lovers will have a wonderful time visiting the Carla Massoni Art Gallery that is located in the historic area of town. History buffs, consider visiting Historical Society-Kent County, a society dedicated to preserving historic art pieces and documents that are related to the county’s history. The town has numerous accommodations and lodging facilities for all types of visitors. For great accommodation and a homey stay, continue reading to find out more about the top Airbnb vacation rentals in Chestertown, Maryland, USA.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 05, 2024.
1. Cozy apartment in a peaceful neighborhood (from USD 151)
You will find this home for rent in Chestertown, Maryland, only two blocks away from downtown that is bustling with the best shops and restaurants.
Located on the third floor, this cozy apartment is an ideal choice for couples. Guests can enjoy magical views of the Chester River from the rooftop deck that overlooks the pristine waterscape. The serenity of the neighborhood makes this Airbnb one of the best places to stay in the midst of nature.
A king-sized bed in the bedroom ensures a good night’s rest. Air conditioning and heaters provide comfort all year round. A high-speed internet connection lets you go about a smooth day of remote work if needed. You can also video-call folks back home without any lag. A full kitchen is equipped with everything that you might need for fixing meals. Kayaks are also supplied for a fun day on the river.
Top guest reviews
Amenities & Room:
incredibly comfortable bed and couchlovely attic apartment with a private patio and wonderful views of the riververy nice apartment with a river viewthe apartment - it really feels like a true apartment- is very well equipped and comfortablebathroom and bedroom were excellentCleanliness:
accommodations were very clean and tidythe apartment was clean and comfortable with everything we needed for a restful stayHost:
the hosts made us feel like we were at home incredibly kind people and very welcominggreat experience and great hoststhey were very responsive in communications and very accommodatingfranco and daryl are excellent hostsfranco was so helpful and responsive every time i reached outRead more reviewsLocation:
great location walking distance to several shops and restaurantsyou are walking distance to great shops and restaurantsgreat location near the waterfront and downtownwe could easily walk to the restaurants and shops on and near high streetwe loved the location along the water
2. Historic house with a garden (from USD 122)
This pet-friendly rental in Chestertown, Maryland, is only a four-block walk from Fountain Park and the historic downtown. The century-old house rests along the harboring banks of the Chester River. Minutes away from the quiet High Street, the three-story Airbnb is a great place to stay for the ones who are searching for a sanctuary of tranquility.
The air-conditioned interior is impeccably designed with elegant furnishings and warm lighting that lend this classic house a refined vibe. Guests can wind down on the plush sofa and watch television during the hours when they stay indoors. The house also opens out onto a well-maintained garden. A reposeful afternoon of reading can be spent here while soaking up the sun.
Top guest reviews
Amenities & Room:
having 2 rooms lets you relax and spread outboth beds on the third floor were comfortable to sleep inthe third floor suite was private very spacious and extremely comfortablebeautiful 3rd floor apartmentCleanliness:
clean quiet and comfortableour room was clean and well appointedthe house was beautiful very clean and invitinglovely convenient clean and affordableterrific accommodations with plenty of room and very cleanHost:
lovely hosts and lovely placejim and gale were wonderful hoststhey were friendly and hospitableand our hosts were welcoming and engagingjim and gale are accommodating and friendly hostsRead more reviewsLocation:
very close to town and some outstanding restaurantssuch a lovely place right next to washington collegewe loved the house and it’s locationwonderful stay great location terrific hostslocation was wonderful and we had some great walks
3. Historic Chestertown (from USD 325)
The rentals’ design is all about making the guests feel comfortable and relaxed. All the three bedrooms and other areas in the home are very spacious. This accommodation in Chestertown, Maryland, is good for five guests and has two-and-a-half baths, a kitchen, an entertainment room, and some porches for guests to enjoy the cool river breeze. Visitors can use the kitchen and its state of the art equipment to prepare their meals. The cathedral ceiling in the masters’ bedroom and bath allow proper air circulation for added cooling. There is parking available on the street just in front of the house.
Top guest reviews
Amenities & Room:
carey made our stay very comfortablethe kitchen is very open with excellent appliances with an adjacent beautiful outdoor deck spacethe master bed was like sleeping on a cloudeverything was easy - communications check-in check-out wifi rokuwe loved spending time in the open kitchen/living room area as well as the covered patioCleanliness:
meticulously cleansparkling clean beautifully decorated and uniqueeverything was clean accessible and comfortablethe house is always very clean and extremely well appointedup stairs bed were very comfortable and bathrooms clean and well equippedHost:
the host is very responsivegorgeous home and gracious hostthe host made us feel very welcomeour host was easy to communicate with and available for any questions we hadhe was quick to respond to our questions and most helpful with local restaurantsRead more reviewsLocation:
great location in chestertowngreat location - walking distance to all the spots downtownthe location is perfectgreat house great locationthis house is a perfect location to downtown chestertown
4. Townhouse in the heart of Chestertown
Owned by a friendly couple, this rental has that old world charm that everybody will love. However, what guests really rave about is its location. Travelers who choose to stay here find themselves residing close to the Saturday Farmer’s Market, various shopping stores, a comprehensive bookstore, cafes, restaurants, a delectable bakery, and the town’s main lifeblood, the Chester River. This convenience cuts back on transportation expenses. For those who want to burn some calories off, quite a number of walkways are found close by. It can host a maximum of 4 guests in its two bedrooms and two-and-a-half bathrooms. The unit is not safe for children under 12 years old.
Chestertown, Maryland, United States
407 meters (0.3 ft) from Wilmer ParkAccommodates: 4
Top guest reviews
Amenities & Room:
lots of comfortable chairs in the bright and cheerful back living roomthe sitting rooms and lovely patio and gardens are great places to settle in after sightseeingwe were completely comfortable during our entire visitCleanliness:
the house was neat and cleanthe house was clean and phyllis and pere were there to great us and walk us through everythingthis is a very clean beautiful well located hometheir home is beautiful clean filled with everything you need and in a great walkable locationtheir home is so clean and organized and the location is just greatHost:
our hosts were amazingphillis and pere were excellent hostshosts were lovely and graciousthey are great hoststhank you for being such welcoming hostsRead more reviewsLocation:
the location is idealgreat location for anytimethis location is charming and within walking distance to everything in townnot to mention the location is perfectclose to the water walking distance to great little shops and the farmer’s market on saturday is wonderful
5. Merry manor
Pet lovers will be happy to know that they can bring their four-legged friends inside this wonderful and beautiful rental located right in the middle of town. The three bedroom manor is good for six guests and has a spacious living/dining area, a well-equipped kitchen, and one-and-a-half bathrooms. The pet-friendly porch is where travelers can sit and watch their cat or dog run around without the fear of losing them. It comes with a parking garage good for one vehicle and an additional three more along the driveway. It only takes a few minutes to venture into town, where guests can enjoy the best restaurants, cafes, and a whole lot of antique shopping.
Chestertown, Maryland, United States
2.84 km (1.8 mi) from Wilmer ParkSuperhost
Accommodates: 6
Top guest reviews
Amenities & Room:
plenty of room in merry manor nice to have a fenced yard for our dogsmerry manor was everything we had hoped - clean comfortable and quiet with all the amenities we neededthe house was house was equipped with everything we needed for a more than comfortable stayCleanliness:
very clean convenient check inplace was clean and comfortableextremely clean and comfortableeverything was clean and sparklingit was very clean and comfortableHost:
she is an excellent hostthe owners are greatthe owners were kind and flexiblethank you to sharon and susan for being such welcoming hostssusan is a wonderful host very communicativeRead more reviewsLocation:
great location - very conveniently located to stores restaurants and downtownlocation is great if you’re needing to be close to the college or downtownthe location couldn’t be betterperfect location to washington college and downtown chestertown businessesgreat location very close to chestertown and rock hall
6. Waterfront with pier and walking distance to Chestertown (from USD 461)
The place has four bedrooms and can fit eight guests with a lot of space to spare. With the recent renovation, the rental now has a stylish décor with a lot of amenities designed to entertain a big group of travelers. Gourmet meals can be prepared in the fully equipped kitchen. All the meals can be savored in the breakfast area or dining room, or in the much spacious outdoors on the porch or near the fire pit. Included in the rental are facilities for paddle boarding, fishing, crab picking, hammock, a pier, and canoeing.
Top guest reviews
Amenities & Room:
very comfortable furniture and bedsthe beds were super comfy with luxury linensbeautiful house great kitchen facilities outstanding screen porch huge backyard and the dock with paddle boards and canoethe home is as comfortable as they come and the location and view cannot be beatsuper comfortable beds fancy showers plenty of space to spread out and lounge both indoors and outdoorsCleanliness:
it was very clean comfortable and spaciousthe house itself was clean and had everything we neededthe inside area was clean spacious and well appointedbeth was so responsive and the house was immaculately clean can't recommend enoughit’s extremely comfortable clean and up to dateHost:
host is very helpfullovely home and fantastic response from owner - 5 starbeth the host is extremely accommodating and truly wants you to enjoy her homevery communicative and easy hostbeth is a wonderful host with a mystical sense of detailRead more reviewsLocation:
the location is perfect with access to the river and proximity to townabsolutely beautiful home in a fabulous locationlovely home in a convenient location short drive to downtown chestertownit is in a prime location with amazing river viewsa great place for a family getaway
7. Spacious apartment in the heart of town
Centrally located, this apartment offers a comfortable refuge for Chestertown travelers. Shops, cafes, bars, restaurants, and other places of interest can easily be reached by foot, perfect for visitors looking to wander, browse, and admire through this historic town. The interior space is quite roomy and can accommodate up to four. It also features huge windows not only to provide a view of the outdoors, but to allow plenty of natural light in.
354 meters (0.3 ft) from Wilmer ParkAccommodates: 4
Top guest reviews
Amenities & Room:
we enjoyed the space tremendously (natural light king bed great kitchen old fashioned feel etcall the comforts of home- we were very comfortable and had all we neededlarge comfortable bed large bathroom well equipped kitchenthe main bedroom and bed are fantasticwe spent an entire afternoon in that room just enjoying and relaxingCleanliness:
spotlessly clean; pictures were accurateit was also very clean and well-stockedthe apartment is spacious and cleanspacious and clean one bedroom apartment in downtown chestertownthe apartment was very comfortable clean and well locatedHost:
sarah was responsive and helpful to speak tosuch friendly service and kind hospitality from hostssarah was a great host and responded quickly to questions we hadsarah was an outstanding and very accessible hostsarah is a great host and extremely helpful and responsiveRead more reviewsLocation:
easy walk to all spots and right across from the saturday farmers marketlocation location location wonderful spot in the heart of chestertowngreat location in the center of towngreat location convenient to all of downtownthe apartment has a perfect location in downtown chestertown easy walking distance to everything
8. Delightful carriage house near downtown (from USD 106)
If you’re looking to explore on your next Chestertown trip, this is definitely the accommodation you’ll need. Situated just a few blocks from the downtown area, pretty much everything—from commercial establishments to local attractions—can easily be reached by foot or bike. It also sits in a quiet neighborhood, providing guests with a peaceful ambience. The rental has a fireplace, air-conditioning, Wi-Fi, TV, and other essentials to ensure a leisurely stay.
Top guest reviews
Amenities & Room:
the cottage had everything we needed for a very comfortable getawayhaving a tesla charger in the garage was super convenientas another reviewer mentioned the space is much cozier and cuter than the pictures showcomfy bed ice-cold a/c and amazing shower water pressure thanksthe carriage house is the perfect cozy space for two peopleCleanliness:
clean and attractive apartmentclean and had everything i neededeverything was spotless and very comfortablethe place was very cleanthe carriage house is bright clean quiet and convenientHost:
roland is an excellent host very helpful & responsiveRead more reviewsLocation:
the location is greatwonderful location - close to everything in townvery nice location and very comfortable spacethis is a great location: close to everything in town yet very quietroland's place is perfectly situated in chestertown
9. Homey abode in a quiet neighborhood (from USD 256)
Great for big families and group of friends, this home rental has more than enough space to accommodate up to ten guests. It has five bedrooms, kitchen, dining area, living room, and patio furnished with modern necessities to ensure comfort and convenience. High-speed Wi-Fi connectivity is also available for all your devices. It’s location in the historic district provides guests easy access to many attractions in town.
Top guest reviews
Amenities & Room:
the beds were very comfortablean absolutely beautiful home super comfortable beds and beddingcomfortable beds and linensthe patio and upstairs porch are well appointed and comfortable; there are thoughtful touches throughoutthe house is very comfortable and the setting was charmingCleanliness:
nice clean and plenty of roolmhouse was clean and perfect environment for our staysoap dishwasher tablets toilet items linens pillows and towels were generous new and cleanbeth and bob's place is amazing beautiful and completely spotlessgreat stay quick easy communication easy check in very nice guidebook extremely clean right in townHost:
they were fabulous hoststhe little caring touches spoke volumes of the hospitality of our host and hostesshosts are awesome and very responsivethe hosts couldn't have been more helpful and attentivejust amazing bob and beth were wonderful hosts and we absolutely loved their homeRead more reviewsLocation:
good location and beautiful homethe location was perfect for a short walk to town for a bite or shoppingit is in the perfect location amazing space and wonderful for childrenit's so close to downtown we walked everywhere and back again without any troubletheir home's backyard and gardens provide an idyllic location to relax
10. Relaxing home with marina view (from USD 285)
Located right by the marina, this home provides guests a panoramic view of the river. The location is also great for visitors as it’s near shopping, dining, and tourist destinations in town. The home has three bedrooms with four comfy beds, a fully equipped kitchen, heating and cooling, and a living area with comfy couches and TV. The second floor balcony has a sitting area if you just want to sit back, relax, and take in the beautiful views.
Top guest reviews
Amenities & Room:
it would fit 4 people comfortably (1 per bed)firm good mattresses decent cable tv selection good lighting plenty of towelsthe stylishly decorated apartment is spacious quiet and comfortable with a lovely view of the marina and riverCleanliness:
it was very clean and comfortableit’s clean and in the perfect locationthe home is clean neat and adorableclean comfortable accommodations friendly hospitable owners in a delightful townhuge bathroom cool little loft high ceilings extremely cleanHost:
the hosts were friendly and helpfulthis airbnb has great hostswalter and marjorie were excellent hoststhe hosts were very kind and friendly and gave great recommendations for the townwalter and marjorie were welcoming hostsRead more reviewsLocation:
best location in chestertownperfect location and extremely comfortablethis is an ideal location on the water in downtown chestertownwalter's airbnb is the perfect location and facility for your trip therethe location on the waterfront and just a few blocks from the center of chestertown is ideal
11. Lovely Victorian home with modern amenities (from USD 356)
Great for family getaways, this charming Victorian home has more than enough space to accommodate up to twelve guests. The classic design is complemented with modern amenities such as Wi-Fi, cable TV, fridge, microwave, and more to provide guests with entertainment and convenience. It’s also centrally located within the Historic District, which means that you’ll enjoy the peaceful setting while providing you easy access to coffee shops, restaurants, retail shops, the river, and other local attractions.
Top guest reviews
Amenities & Room:
smart tv and comfy chairs allowed for good movie watchingcozy stylish and comfortable house with all the amenitiesthe beds were comfortable for sleepingthe house was very clean and the mattresses and furniture were all comfortablethe house was so well-equipped and so comfortable with plenty of space for everyoneCleanliness:
the house is beautiful very clean and well stockedwell kept clean and beautifully decoratedbeautiful home spacious and very cleansparkling clean nice quiet locationthe beds were very comfortable and the house was neat and cleanHost:
very responsive hostryla is a fantastic hostthe hosts were truly special - wonderful incredibly accommodating and graciousi would absolutely recommend a stay with this hostryla was very accommodating and the whole process (from booking to checkin/checkout) was smooth and easyRead more reviewsLocation:
the location is wonderful both in its location and proximity to chestertownperfect vacation house and locationgreat location for a weekend getawayit is wonderfully situated close to everythingamazing property and great location
12. Victorian-style row house near downtown (from USD 208)
Close to restaurants, shops, bars, cafes, river, and other attractions in town, this home rental is the perfect home-base for your next Chestertown trip. Aside from its location, guests will be treated to a peaceful surrounding as it sits in the middle of a safe and quiet side street. The home has a charming Victorian design inside and out. The classic ambience is enhanced with modern amenities like air-conditioning, Wi-Fi, TV, and more to ensure the most relaxing stay.
Top guest reviews
Amenities & Room:
thanks for a comfortable stay and we would definitely rent againthe master bedroom is spacious and comfortable with a wonderful balconythe linens were crisp the bathrooms were updated the carpets and rugs throughout were cleanthe second floor had two very comfortable bedswith beautiful updates in the kitchen particularly but also throughout the rest of the houseCleanliness:
roomy clean and reasonably pricedthe house is beautiful and very cleanthe beds are comfortable and the bathrooms as the whole home is spotlessly cleanclean and comfortable it is a great get-away we hope to re-book for future visitsroland is a great host the house was clean and convenient and we would definitely rent it againHost:
roland is a wonderful host and responded quickly to questionsvery responsive hosthost is very good at communicatingthe host provided great tips for what to do in the areacute home and great hostRead more reviewsLocation:
nice walking distance to townperfect location for a chestertown visitgreat location and beautiful houseeasy walk to towngreat place and great location
13. Chestertown house
This rental is a beautifully renovated house that sits near the famous Chester River. It can accommodate a family of six with it’s three fully appointed bedrooms and two-and-a-half baths. Families can spend time with each other in a number of areas within the property, such as the living room, the kitchen, the den, and the terrace located at the backyard. A long driveway provides parking spaces for a number of vehicles. The best part of this house is the location. The property is situated a few minutes walk away from the historic sites of the town, the farmer’s market, and the finest restaurants and shops that one can find.
969 meters (0.7 ft) from Wilmer Park
14. Cozy house located a level above businesses
This house imbibes a welcoming feeling that makes it so relaxing and comfortable. Guests can occupy and use the upstairs bedroom and bathroom. The vacation rental can accommodate a maximum of three individuals. Common spaces such as the kitchen and porch, located downstairs, is shared with the salon employees who work on the ground floor. The salon is open until 6 PM on Mondays to Fridays, and 2:30 PM Saturdays. The location of the place is so attractive because it lies just a few minutes away from the downtown area. Guests can opt to bike or walk to the downtown area through a safe pathway.
2.11 km (1.4 mi) from Wilmer Park
15. Victorian home for six
This rental is situated inside a historic home that was built in1890. All three bedrooms offer a fantastic view of the majestic waters of the Chester River. These bedrooms have their own bathrooms. A comfortable porch welcomes guests by the entrance. Aside from that, the place is also fitted with a fancy kitchen, a library, a dining room, and a huge living area. Throughout the home, natural lighting that filters in from wide windows. Out in the backyard, guests can have access to the barbecue grill. The property sits very near some of Chestertown’s top places of interest like the Marina, Fountain Park, and its famous dining and shopping venues in the downtown district.
716 meters (0.5 ft) from Wilmer Park
16. Charming and cozy Victorian cottage
The consensus amongst previous guests of this rental is that the check-in process is a breeze. This perk surely is an added convenience for everyone who wants to stay in this recently refurbished home. The rental has concrete counters that adds to form and functionality in the kitchen. It can easily accommodate four guests distributed across two well-appointed bedrooms. The indoor area has a wine bar where guests can enjoy a relaxing bottle and some friendly conversation. The backyard is built for entertaining as well. With a table set for all the guests, the backyard patio and garden can become a place where everyone can share stories and fun moments.
Chestertown, Maryland, United States
868 meters (0.6 ft) from Wilmer Park
17. Cozy apartment in Chestertown
This vacation rental is situated in a locality that is ideal for couples who want to immerse themselves in the town’s rich history and artistic nature. Fitted with a bedroom and a living/dining/ kitchen area, guests can settle in comfortably and be residing near the city’s main attractions. Fountain Park is just a few blocks away and so is the illustrious Chester River. Furthermore, there are so many places located within proximity of the vacation rental where guests can enjoy the works of local painters, musicians, writers, and sculptors. Parking is available for one vehicle. The place is not suitable for pets and children under two years of age. Visitors can rent this place for short or long term stay.
Chestertown, Maryland, United States
806 meters (0.6 ft) from Wilmer Park
18. Charming apartment in Chestertown
The rental is good for two guests, perfect for honeymooners and couples who want to spend some quality time in Chestertown. It is fitted with a full kitchen, a dining area for two, and an artistic living room designed with reclaimed wood from Chora Studio and a customized carpet by artist, Faith Wilson. Travelers can relax by taking a cool bath or shower in its elegant bathroom. An open deck with a table and chairs welcome every guest as they walk through the rentals’ entrance. The downtown area and Washington College are both situated a short distance away. The rental provides parking for one vehicle.
Chestertown, Maryland, United States
732 meters (0.5 ft) from Wilmer ParkAccommodates: 2
Top guest reviews
Amenities & Room:
the hosts francesca and leslie were great and available including stocking coffee and breakfast itemsexcellent communicator complimentary items in the fridge nice bed and pillows window ac unit does the jobwhat a great place comfortable bed coffee creamer ofrancesca’s apartment is easy to get to with parking availablethey left breakfast items like coffee bread milk and oj as wellCleanliness:
everything was clean and operationalextremely clean and very cozypeaceful clean had everything we neededgreat and homey spot it was clean and comfortableHost:
host was very easy to reach and super helpfula wonderful host who is quick to respondthe cozy apartment was great and the hosts wonderfulthe owner is a very good communicator and bends over backwards to accommodate her guestsRead more reviewsLocation:
very cute apartment close to everythinga charming apartment close to towncute place and great locationa nice safe location close to townthe property’s location is excellent & everything is within walking distance
Visit Chestertown!
These warm and cozy places to stay in Chestertown, Maryland, are all situated close to the Chester River and are managed by some of the friendliest hosts one will ever find. All these are just minutes away from the most famous landmarks the town has to offer. What are you waiting for? Book your dream Airbnb vacation rental today!
Frequently asked questions about Airbnb vacation rentals in Chestertown
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