Top 10 Airbnb Vacation Rentals In Chestertown, Maryland - Updated 2021

airbnb Chestertown Md, Usa

Chestertown is located on the eastern side of Maryland. The historic town is known for two types of residents - the ‘from-here’ and the ‘come-here’. The former are those who have been living in the town for more than three generations. The latter is made up of those who just recently settled in. Its etymology comes from the river it was named after - 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 cost-friendly and accommodating board and lodging facilities for all types of visitors. Read on, and check out our top ten Airbnb vacation rentals in Chestertown, Maryland and choose the one that best suits your needs.

1. Historic Chestertown (from USD 279)

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 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.

Historic Chestertown
Chestertown, Maryland, United States
124 reviews
Entire house 3 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
carey made our stay very comfortable
the kitchen is very open with excellent appliances with an adjacent beautiful outdoor deck space
the master bed was like sleeping on a cloud
everything was easy - communications check-in check-out wifi roku
we loved spending time in the open kitchen/living room area as well as the covered patio
meticulously clean
sparkling clean beautifully decorated and unique
everything was clean accessible and comfortable
the house is always very clean and extremely well appointed
up stairs bed were very comfortable and bathrooms clean and well equipped
the host is very responsive
gorgeous home and gracious host
the host made us feel very welcome
our host was easy to communicate with and available for any questions we had
he was quick to respond to our questions and most helpful with local restaurants
great location in chestertown
great location - walking distance to all the spots downtown
the location is perfect
great house great location
this house is a perfect location to downtown chestertown
Read more reviews

2. Townhouse in the heart of Chestertown (from USD 200)

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.

Town House in the Heart of Chestertown
Chestertown, Maryland, United States
127 reviews
Entire house 3 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
lots of comfortable chairs in the bright and cheerful back living room
the sitting rooms and lovely patio and gardens are great places to settle in after sightseeing
we were completely comfortable during our entire visit
the house was neat and clean
the house was clean and phyllis and pere were there to great us and walk us through everything
this is a very clean beautiful well located home
their home is beautiful clean filled with everything you need and in a great walkable location
their home is so clean and organized and the location is just great
our hosts were amazing
phillis and pere were excellent hosts
hosts were lovely and gracious
they are great hosts
thank you for being such welcoming hosts
the location is ideal
great location for anytime
this location is charming and within walking distance to everything in town
not to mention the location is perfect
close to the water walking distance to great little shops and the farmer’s market on saturday is wonderful
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3. Merry manor (from USD 125)

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.

Merry Manor Pet Friendly Home
Chestertown, Maryland, United States
121 reviews
Entire house 4 Beds 3 Bedrooms 1 Bathrooms
Top guest reviews
Amenities & Room:
plenty of room in merry manor nice to have a fenced yard for our dogs
merry manor was everything we had hoped - clean comfortable and quiet with all the amenities we needed
the house was house was equipped with everything we needed for a more than comfortable stay
very clean convenient check in
place was clean and comfortable
extremely clean and comfortable
everything was clean and sparkling
it was very clean and comfortable
she is an excellent host
the owners are great
the owners were kind and flexible
thank you to sharon and susan for being such welcoming hosts
susan is a wonderful host very communicative
great location - very conveniently located to stores restaurants and downtown
location is great if you’re needing to be close to the college or downtown
the location couldn’t be better
perfect location to washington college and downtown chestertown businesses
great location very close to chestertown and rock hall
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4. Waterfront with pier and walking distance to Chestertown (from USD 532)

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.

Waterfront w/Pier &Walking Distance to Chestertown
Chestertown, Maryland, United States
58 reviews
Entire house 5 Beds 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
very comfortable furniture and beds
the beds were super comfy with luxury linens
beautiful house great kitchen facilities outstanding screen porch huge backyard and the dock with paddle boards and canoe
the home is as comfortable as they come and the location and view cannot be beat
super comfortable beds fancy showers plenty of space to spread out and lounge both indoors and outdoors
it was very clean comfortable and spacious
the house itself was clean and had everything we needed
the inside area was clean spacious and well appointed
beth was so responsive and the house was immaculately clean can't recommend enough
it’s extremely comfortable clean and up to date
host is very helpful
lovely home and fantastic response from owner - 5 star
beth the host is extremely accommodating and truly wants you to enjoy her home
very communicative and easy host
beth is a wonderful host with a mystical sense of detail
the location is perfect with access to the river and proximity to town
absolutely beautiful home in a fabulous location
lovely home in a convenient location short drive to downtown chestertown
it is in a prime location with amazing river views
a great place for a family getaway
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5. 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.

Chestertown House
18 reviews
Entire house 4 Beds

6. 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.

Private rooms above businesses
15 reviews
Entire house 1 Bed

7. 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.

EAST OF THE MOON Historic Victorian on Water St.
8 reviews
Entire house 3 Beds

8. 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.

Charming & Cozy Victorian Cottage
Chestertown, Maryland, United States
79 reviews
Entire cottage 2 Beds 2 Bedrooms 1 Bathrooms

9. 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.

Cozy 1st Floor Apartment in Chestertown
Chestertown, Maryland, United States
67 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom

10. 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.

Charming 2nd Floor Apartment in Chestertown
Chestertown, Maryland, United States
107 reviews
Entire apartment 1 Bed 1 Bedroom 1 Bathroom

Visit Chestertown!

These warm and cozy Airbnb vacation rentals located in Chestertown 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!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Hi! I'm Gabby. Writing, travel, and food are my passion. These three bring me to new highs. What better way to enjoy life than to experience all my passion at this stage of my life. I've been...Read more

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