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
Guesthouse in Annapolis
4.9 out of 5 average rating, 208 reviewsCalico Cottage Guest House, king bed, free parking
Mar 16 – 23
Farm stay in Essex
4.95 out of 5 average rating, 140 reviewsPrivate wing at historic water view Walnut Grove
Jul 28 – Aug 4
Apartment in Chestertown
4.92 out of 5 average rating, 97 reviewsDowntown Studio Apartment
Mar 22 – 29
Apartment in Chestertown
5.0 out of 5 average rating, 69 reviewsWaterfront historic district 1BR Apartment
Jul 24 – 31
Guest suite in Chestertown
4.94 out of 5 average rating, 48 reviewsHistoric Downtown Garden Oasis with Private Patio
Nov 16 – 23
Home in Chestertown
4.98 out of 5 average rating, 44 reviews2 Beds, 2.5 Baths, Perfect Downtown Location
Jun 5 – 12
Home in Chestertown
4.89 out of 5 average rating, 27 reviewsBeautifully remodeled home in Historic Chestertown
Jul 27 – Aug 3
Home in Chestertown
4.96 out of 5 average rating, 73 reviewsCozy 3-bedroom home w/ screened in porch & firepit
Dec 5 – 12
Other great vacation rentals in Chestertown
Home in Chestertown
5.0 out of 5 average rating, 13 reviewsNEW Chestertown Retreat
Sep 1 – 8
Home in Chestertown
5.0 out of 5 average rating, 38 reviewsWaterfront house with private dock & kayaks!
Dec 15 – 22
Apartment in Rock Hall
4.96 out of 5 average rating, 47 reviewsBayside bungalow cottage by the sea
Jan 1 – 8
Home in Chestertown
5.0 out of 5 average rating, 24 reviewsMagnolia House ~Historic Downtown w/Private Garden
Feb 5 – 12
Apartment in Chestertown
4.92 out of 5 average rating, 62 reviews1-br apt in downtown Chestertown
Jun 22 – 29
Home in Chestertown
5.0 out of 5 average rating, 21 reviewsIn Town Chestertown Rancher (1 Block to College)
Feb 5 – 12
Home in Chestertown
4.94 out of 5 average rating, 31 reviewsHarbor View Haven | Waterfront w/ HOT TUB + Dock!
Jul 13 – 20
Home in Chestertown
5.0 out of 5 average rating, 16 reviewsDown by the River
Dec 30 – Jan 6
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 self check-in, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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