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Vacation rentals in Chestertown
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Chestertown
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chestertown vacation rentals
Other great vacation rentals in Chestertown
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Home in Chestertown
4.92 out of 5 average rating, 166 reviewsHistoric Chestertown
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Apartment in Essex
4.97 out of 5 average rating, 226 reviewsA place unique on sue creek
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Apartment in Greenwood
4.97 out of 5 average rating, 487 reviewsBeach Highway Hobby Farm
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Cottage in North East
4.97 out of 5 average rating, 451 reviewsPersimmon Pastures
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Apartment in Chestertown
5.0 out of 5 average rating, 70 reviewsWaterfront historic district 1BR Apartment
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Apartment in Chestertown
4.92 out of 5 average rating, 97 reviewsDowntown Studio Apartment
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Home in Chestertown
4.98 out of 5 average rating, 46 reviews2 Beds, 2.5 Baths, Perfect Downtown Location
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Guest suite in Chestertown
4.94 out of 5 average rating, 50 reviewsHistoric Downtown Garden Oasis with Private Patio
Other great vacation rentals in Chestertown
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Home in Chestertown
4.94 out of 5 average rating, 33 reviewsHarbor View Haven | Waterfront w/ HOT TUB + Dock!
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Home in Chestertown
5.0 out of 5 average rating, 77 reviewsRiver front cottage with private dock & water fun
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Home in Chestertown
5.0 out of 5 average rating, 18 reviewsDown by the River
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Home in Chestertown
4.87 out of 5 average rating, 31 reviewsBeautifully remodeled home in Historic Chestertown
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Home in Chestertown
5.0 out of 5 average rating, 25 reviewsMagnolia House ~ Historic Downtown, Private Garden
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Home in Greensboro
4.96 out of 5 average rating, 50 reviewsCozy 2 bedroom home on wooded private lane
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Home in Chestertown
5.0 out of 5 average rating, 54 reviewsLovely Home in Chestertown With Free EV Charging
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Home in Chestertown
5.0 out of 5 average rating, 15 reviewsNEW Chestertown Retreat
Quick stats about vacation rentals in Chestertown
Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
2.5K reviews
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Chestertown?
Yes! Work meets play with ease at over 20 vacation rentals in Chestertown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chestertown?
Four-legged friends are welcome in Chestertown. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Chestertown have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Chestertown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chestertown have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Chestertown. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chestertown have wifi?
Absolutely! We offer over 20 house rentals with wifi in Chestertown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Chestertown?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with a bbq area, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
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