This 19th-century retreat, located in Still Pond, offers an apartment just a 15-minute drive from historic Chestertown and is conveniently situated near Rock Hall, Betterton Beach, Georgetown, and local vineyards. This 42 square meter apartment accommodates up to three guests, featuring a private living room with a pullout sofa, a queen bedroom with a Purple mattress, an en-suite bathroom with a multi-head shower, and an in-suite kitchenette, with shared access to a wraparound porch and farmhouse deck ideal for boaters.
10 13 reviews
Chestertown, MD
20/07 – 23/07
SG$297/nighttotal: SG$891 (3 )
Walk To Historic Chestertown: Dog-friendly Retreat
2 2
apartment , Chestertown
This Chestertown property, a two-bedroom, two-bathroom flat, is located near historic streets and the Chester River, offering convenient access to downtown attractions, including art galleries, and Wilmer Park, all within 1 kilometre of the accommodation. This pet-friendly apartment accommodates up to six guests and features a well-equipped kitchen with a Cuisinart dual coffee maker, air conditioning, a fireplace, a fenced garden with a furnished deck, and off-street parking.
10 16 reviews
Chestertown, MD
03/07 – 08/07
SG$1592/nighttotal: SG$7960 (5 )
Stepne Manor
1 2
apartment , Chestertown
Stepne Manor is a five-bedroom house situated in the historic district of Chestertown, Maryland, a short walk from Fountain Park, the Chestertown Marina, and Wilmer Park on the Chester River. This property has received excellent ratings for its location, cleanliness, and overall user experience. The house comfortably accommodates 15 guests and features a private suite with a Jacuzzi tub. Guests can enjoy a range of amenities including a garden, a terrace, and a spa, as well as modern comforts like air conditioning, satellite TV, and a fully equipped kitchen.
10 4 reviews
Chestertown, MD
20/07 – 23/07
SG$360/nighttotal: SG$1080 (3 )
Walk To Historic Chestertown: Dog-friendly Retreat
2 2
apartment , Chestertown
This Chestertown residence is a 14-minute walk from the Kent County Historical Society and a 15-minute walk to Wilmer Park, offering convenient access to local attractions. This 90 square metre holiday home accommodates up to six guests, featuring two bedrooms, two bathrooms, a private garden, a terrace, barbecue facilities, and on-site parking.
9.9 57 reviews
Chestertown, MD
20/07 – 23/07
SG$285/nighttotal: SG$855 (3 )
Charming Haven On High
1 2
apartment , Chestertown
This Chestertown apartment is centrally located in the downtown area, a short walk (0.8 km) from the Chester River and Washington College. The two-bedroom, one-and-a-half-bathroom property sleeps four, boasting an updated kitchen with fridge, microwave, and dishwasher, air conditioning, parking, and is within easy reach of the Arts & Entertainment District and numerous festivals.
10 11 reviews
Chestertown, MD
20/07 – 23/07
SG$526/nighttotal: SG$1578 (3 )
Heart Of Historic Chestertown - Church Alley
1 2
apartment , Chestertown
This Chestertown townhouse, located on a quiet street in the historic downtown area, is steps from the farmers' market, Chester River, and numerous restaurants. The two-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen with dishwasher, a private patio for al fresco dining, and free on-site parking; enjoy easy access to local festivals and waterfront walks.
9.0 2 reviews
Chestertown, MD
03/07 – 08/07
SG$342/nighttotal: SG$1710 (5 )
3 Mi To Washington College! Updated Home W/ Patio
3 2
apartment , Kingstown
This 3-bedroom flat is located in a quiet Kingstown neighbourhood, offering excellent birdwatching and a short 3-kilometre drive to the central business district. Guests can enjoy a wood-burning fireplace, a private garden, and keyless entry, with amenities including WiFi, air conditioning, and on-site laundry facilities for up to 4 people.
10 30 reviews
Chestertown, MD
03/07 – 08/07
SG$472/nighttotal: SG$2360 (5 )
Peaceful Retreat On The Eastern Shore. Nature Lovers Paradise!
3 2
apartment , Rock Hall
This three-bedroom apartment is located just 0.8 km from the bay in Rock Hall, a quiet location close to Rock Hall Harbour and Rolphs Wharf Marina. The apartment has received excellent ratings from previous guests. This spacious property can accommodate up to eight guests and features a well-equipped kitchen, a terrace, a garden, and parking for three vehicles. Enjoy the peace and quiet of the location while having easy access to the bay for boating, paddle boarding, kayaking, birdwatching, and cycling.
9.9 83 reviews
Chestertown, MD
20/07 – 23/07
SG$394/nighttotal: SG$1182 (3 )
Loft At Fountain Park - Prime Downtown Location
1 2
apartment , Chestertown
This apartment is situated in the heart of Chestertown, just a short walk from Washington College, the Chester River and the town's historic district, with easy access to shops and restaurants on High Street. The apartment has received excellent ratings for location, cleanliness and overall experience. This spacious property spans two levels and offers four bedrooms, comfortably accommodating up to eight guests. The apartment boasts a fully equipped kitchen, air conditioning, a garden and parking, ensuring a comfortable and enjoyable stay.
10 13 reviews
Chestertown, MD
20/07 – 23/07
SG$689/nighttotal: SG$2067 (3 )
114 High - Upper Floors Apt Chestertown Sleeps 7
1 2
apartment , Chestertown
This three-bedroom apartment in Downtown Chestertown is just a short walk from the town's shops, cafes, and restaurants. The apartment, spread over two floors, comfortably accommodates seven guests and features a fully equipped kitchen, two bathrooms, and free on-street parking.
10 27 reviews
Chestertown, MD
20/07 – 23/07
SG$283/nighttotal: SG$849 (3 )
Last-minute Retreat Center Of C’town -1 Night Stay
1 2
apartment , Chestertown
This studio flat is a secluded retreat in Chestertown, offering over 0.4 hectares of private gardens and convenient access to local attractions. This romantic hideaway accommodates two guests and features a king-size bed, a well-equipped kitchenette with a two-burner hot plate and microwave, a fireplace, and an in-unit washer and dryer, with pets welcome and private parking provided.
9.8 168 reviews
Chestertown, MD
03/07 – 08/07
SG$648/nighttotal: SG$3240 (5 )
Historic Chestertown
1 2
apartment , Chestertown
This charming apartment is situated in the heart of Chestertown's historic district, just a short walk from the town's bustling restaurants, shops, and the picturesque Chester River waterfront. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment has three bedrooms and two bathrooms, comfortably accommodating up to five guests. It features a well-equipped kitchen with modern appliances, a spacious living area, and a private outdoor space with a covered porch and a pergola, perfect for relaxing and enjoying the beautiful surroundings.
Best family friendly Chestertown, MD Holiday Apartments and Self Catering Accommodations
Among the 34 accommodations in Chestertown, MD, here are the 4 best family friendly holiday apartments
10 40 reviews
Chestertown, MD
20/07 – 23/07
SG$748/nighttotal: SG$2244 (3 )
Waterfront Escape & Walk To Historic Chestertown
1 2
apartment , Chestertown
This waterfront house is located just 1 kilometre from the historic downtown area of Chestertown, offering easy access to shops, restaurants, and attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The spacious house has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Enjoy a range of amenities including a fully equipped kitchen, a private garden, a fitness centre, and direct access to the river for kayaking, paddleboarding, and canoeing.
Chestertown, MD
03/07 – 08/07
SG$1684/nighttotal: SG$8420 (5 )
350-acre Waterfront Estate On The Chester River
1 2
apartment , Kingstown
This waterfront estate in historic Chestertown, Maryland, offers direct access to the Chester River and is just minutes from the town's historic district, providing a secluded retreat with extensive natural beauty. This spacious apartment accommodates up to eight guests, featuring a private garden, swimming pool, and parking, with air conditioning, internet, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, ideal for family holidays or group getaways.
10 3 reviews
Chestertown, MD
20/07 – 23/07
SG$435/nighttotal: SG$1305 (3 )
Primrose Cottage~walk To Downtown Chestertown
1 2
apartment , Chestertown
This property is located in Chestertown, within 500 meters of its dining, shopping, and waterfront attractions, and close to the Saturday Farmers Market. This three-bedroom, one-bathroom flat accommodates up to six guests and features a well-equipped kitchen, air conditioning, a garden, and a screened-in porch.
10 1 review
Chestertown, MD
03/07 – 08/07
SG$522/nighttotal: SG$2610 (5 )
Newly Renovated Single Family Home With Attached Guest Suite
5 2
apartment , Betterton
This five-bedroom guesthouse in Worton, a short drive from Betterton Beach, offers convenient access to the Kent Museum and Historical Society of Kent County Maryland and Hidden Lake. The 139 square metre (approximately 1496 square feet) property sleeps ten guests and includes a full kitchen, microwave, fridge, two bathrooms, air conditioning, parking, and Wi-Fi; hunting and birdwatching opportunities are also nearby.
Best Chestertown, MD holiday apartments with a kitchen
10 50 reviews
Chestertown, MD
20/07 – 23/07
SG$332/nighttotal: SG$996 (3 )
Historic Downtown Garden Oasis With Private Patio
1 2
apartment , Chestertown
This Chestertown apartment, centrally located within a 0.6km radius of River Arts Chestertown, the Garfield Center for the Arts, and the Historical Society of Kent County, Maryland, offers easy walking access to cultural attractions and Wilmer Park. The 48 square metre flat features one bedroom, one bathroom, sleeps two guests, and includes a kitchenette with fridge, freezer, and microwave, plus a private fenced yard, balcony, and free Wi-Fi.
9.8 92 reviews
Chestertown, MD
20/07 – 23/07
SG$312/nighttotal: SG$936 (3 )
1-br Apt In Downtown Chestertown (Unit 1)
1 2
apartment , Chestertown
This studio apartment is located just 0.8 kilometres from High Street in Chestertown, Maryland, a short walk from shops, restaurants, and the Chester River. It has consistently received excellent ratings for location, cleanliness, and overall experience. The self-catering apartment is ideal for a couple or solo traveller, featuring a bedroom with a queen-size bed and a private bathroom. Amenities include a fully equipped kitchen, access to streaming services, and a shared garden, making it a comfortable and convenient base for exploring the area.
10 54 reviews
Chestertown, MD
03/07 – 08/07
SG$441/nighttotal: SG$2205 (5 )
In Town Chestertown Rancher (1 Block To College)
1 2
apartment , Chestertown
This Chestertown house, a five-year-old rancher, is conveniently located within walking distance of Washington College and Chestertown's town centre. Sleeping up to 10 guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen with dishwasher, a garden with Weber grill and Solo Stove fire pit, four televisions, central air conditioning and heating, and ample parking; numerous consumables are provided.
9.9 117 reviews
Chestertown, MD
20/07 – 23/07
SG$355/nighttotal: SG$1065 (3 )
2 Beds, 2.5 Baths - Perfect Downtown Location
1 2
apartment , Chestertown
This charming apartment is situated in the heart of historic Chestertown, just a short walk from the town's shops, restaurants and Washington College. It has received excellent ratings for its location, cleanliness and overall user experience. The apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It is well-equipped with modern amenities, including a fully fitted kitchen, high-speed internet, air conditioning, a private garden and parking.
Frequently asked questions about apartment rentals in Chestertown, MD
What are some interesting places to visit in or near Chestertown, MD?
Chestertown is a charming town with plenty to see and do. You could visit the historic Washington College, founded in 1783, and the beautiful Chestertown Riverwalk along the Chester River. A short drive away, you could also explore the Eastern Neck National Wildlife Refuge, a haven for migratory birds.
What are the most popular outdoor activities in Chestertown, MD?
Chestertown is perfect for outdoor lovers. You can go kayaking or canoeing on the Chester River, hike the trails at Millington or Fairlee Park, or enjoy a picnic at Wilmer Park. In the warmer months, you can also go swimming at the Chestertown Beach.
What are the best apartments with a pool in Chestertown, MD?
Chestertown is known for its historic charm, beautiful waterfront, and thriving arts scene. It's also home to Washington College, one of the oldest colleges in the United States. The town is also famous for its annual Chestertown Tea Party Festival, a lively celebration of the American Revolution.
What are the best apartments with a jacuzzi in Chestertown, MD?
What are the top cultural spots to visit in and around Chestertown, MD?
Chestertown has a vibrant cultural scene. You can visit the Academy Art Museum, which showcases contemporary and traditional art, or the Garrison Theatre, a historic venue that hosts a variety of performances. You could also explore the Chestertown RiverArts, a community arts center with galleries and studios.
What are the best apartments for families and kids in Chestertown, MD?
What are the closest cities to visit near Chestertown, MD?
The closest cities to Chestertown are Annapolis, the state capital of Maryland, and Baltimore, a bustling city with a rich history and culture. Both are within a 100 km drive of Chestertown.
What are the best pet friendly apartments in Chestertown, MD?
What are the best ways to relax in Chestertown, MD?
Chestertown is a great place to unwind. You can take a leisurely stroll along the Chestertown Riverwalk, have a picnic in Wilmer Park, or enjoy a glass of wine at one of the many local wineries. You could also rent a bike and explore the town's scenic backroads.
What are the best apartments with parking in Chestertown, MD?
What are the advantages of choosing an apartment for your stay in Chestertown, MD?
Apartments in Chestertown offer more space and privacy than a hotel room. They are also often more affordable, especially for longer stays. Many apartments have kitchens, which allow you to cook your own meals and save money.
Destinations nearby
Best Chestertown, MD holiday apartments with air conditioning
9.9 24 reviews
Chestertown, MD
20/07 – 23/07
SG$483/nighttotal: SG$1449 (3 )
Quiet, Shabby-chic Home In Downtown Chestertown
1 2
apartment , Chestertown
This charming house is situated in the heart of Chestertown, just 0.4 kilometres from Washington College and 0.6 kilometres from the waterfront, offering easy access to the town's attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience. The house provides guests with access to the entire property, comfortably accommodating up to four guests. This spacious home features a fully equipped kitchen, a private garden, a fitness centre, and parking, ensuring a comfortable and enjoyable stay.
Chestertown, MD
20/07 – 23/07
SG$307/nighttotal: SG$921 (3 )
1-br Apt In Downtown Chestertown (Unit 2)
1 2
apartment , Chestertown
This newly furnished one-bedroom flat in Chestertown, available from mid-April 2026, offers guests the chance to be among its first visitors following its conversion to short-term rental, with specific district and landmark proximity to be confirmed post-renovation. This pet-friendly apartment includes a kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, a garden, and accommodates up to two guests, providing a fresh base for exploring the town.
10 5 reviews
Chestertown, MD
20/07 – 23/07
SG$801/nighttotal: SG$2403 (3 )
Stunning Historic Downtown Home!! Within 2 Blocks Of Fountain Park!!
3 2
apartment , Chestertown
This three-bedroom, three-bathroom apartment in Chestertown is situated within 0.32 kilometres of the town centre, offering easy access to shops, restaurants, and the farmers' market. The self-catering property sleeps eight guests and boasts a spacious kitchen/family room, a private patio, and is close to Rolph's Wharf Marina, Cassinelli Winery and Vineyards, Crumpton Auction, and the Hazel Miner Monument.
9.9 123 reviews
Chestertown, MD
20/07 – 23/07
SG$609/nighttotal: SG$1827 (3 )
The Patriot House-chestertown, Md
6 2
apartment , Chestertown
This charming flat in Chestertown is ideally located within walking distance of the town's main attractions, offering easy access to shops, restaurants, and historical landmarks. The apartment has received excellent ratings for cleanliness, location, and overall user experience. The flat is spacious and well-equipped, featuring a large living room, two dining areas, and a laundry room. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking.
Best pet-friendly Chestertown, MD holiday apartments
Among the 34 accommodations in Chestertown, MD, here are the 4 best pet friendly holiday apartments
10 11 reviews
Chestertown, MD
20/07 – 23/07
SG$526/nighttotal: SG$1578 (3 )
Heart Of Historic Chestertown - Church Alley
1 2
apartment , Chestertown
This Chestertown townhouse, located on a quiet street in the historic downtown area, is steps from the farmers' market, Chester River, and numerous restaurants. The two-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen with dishwasher, a private patio for al fresco dining, and free on-site parking; enjoy easy access to local festivals and waterfront walks.
Chestertown, MD
20/07 – 23/07
SG$307/nighttotal: SG$921 (3 )
1-br Apt In Downtown Chestertown (Unit 2)
1 2
apartment , Chestertown
This newly furnished one-bedroom flat in Chestertown, available from mid-April 2026, offers guests the chance to be among its first visitors following its conversion to short-term rental, with specific district and landmark proximity to be confirmed post-renovation. This pet-friendly apartment includes a kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, a garden, and accommodates up to two guests, providing a fresh base for exploring the town.
10 13 reviews
Chestertown, MD
20/07 – 23/07
SG$689/nighttotal: SG$2067 (3 )
114 High - Upper Floors Apt Chestertown Sleeps 7
1 2
apartment , Chestertown
This three-bedroom apartment in Downtown Chestertown is just a short walk from the town's shops, cafes, and restaurants. The apartment, spread over two floors, comfortably accommodates seven guests and features a fully equipped kitchen, two bathrooms, and free on-street parking.
10 27 reviews
Chestertown, MD
20/07 – 23/07
SG$283/nighttotal: SG$849 (3 )
Last-minute Retreat Center Of C’town -1 Night Stay
1 2
apartment , Chestertown
This studio flat is a secluded retreat in Chestertown, offering over 0.4 hectares of private gardens and convenient access to local attractions. This romantic hideaway accommodates two guests and features a king-size bed, a well-equipped kitchenette with a two-burner hot plate and microwave, a fireplace, and an in-unit washer and dryer, with pets welcome and private parking provided.