Vacation rentals in Chestertown
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Top-rated vacation rentals in Chestertown
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Home in Chestertown
4.94 out of 5 average rating, 127 reviewsCHESAPEAKE SUNSETS
Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.
Aug 6 – 13
Home in Chestertown
5.0 out of 5 average rating, 151 reviewsHistoric house, near town center, pet friendly
Renovated 19th century home with all modern conveniences. First floor bedroom with private bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from both Washington College and the C'town waterfront. 2 primary bedroom suites (one on the second floor has a king bed) 2 more bedrooms with queen beds. 1 loft which is connected to the a 2nd story bedroom has 2 twins. Fenced yard and over an acre of totally private gardens. Fire pit.
Dec 10 – 17
Cabin in Chestertown
4.98 out of 5 average rating, 215 reviewsRivershore Retreat
Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.
Apr 4 – 11
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
Apartment in Pasadena
4.99 out of 5 average rating, 542 reviewsSea Dreamer aka Phenomenal Hospitality
Nov 16 – 23
Guesthouse in Annapolis
4.9 out of 5 average rating, 202 reviewsCalico Cottage Guest House, king bed, free parking
Nov 14 – 21
Home in Grasonville
4.94 out of 5 average rating, 221 reviewsRiver Front, Private Single Family Home
Dec 22 – 29
Home in Annapolis
4.96 out of 5 average rating, 103 reviewsHistoric Downtown in-law suite
Jan 9 – 16
Apartment in Chestertown
5.0 out of 5 average rating, 64 reviewsWaterfront historic district 1BR Apartment
Feb 3 – 10
Apartment in Chestertown
4.92 out of 5 average rating, 95 reviewsDowntown Studio Apartment
Jan 4 – 11
Guest suite in Chestertown
4.93 out of 5 average rating, 45 reviewsHistoric Downtown Garden Oasis with Private Patio
Sep 10 – 17
Casa particular in Chestertown
4.93 out of 5 average rating, 99 reviewsRed, White & Waterview Studio Apt with pool
Nov 26 – Dec 3
Home in Chestertown
4.96 out of 5 average rating, 69 reviewsCozy 3-bedroom home w/ screened in porch & firepit
Jan 14 – 21
Home in Chestertown
4.98 out of 5 average rating, 40 reviews2 Beds, 2.5 Baths, Perfect Downtown Location
May 8 – 15
Apartment in Chestertown
5.0 out of 5 average rating, 44 reviewsBright, new apartment in the heart of Chestertown
Dec 2 – 9
Home in Chestertown
4.88 out of 5 average rating, 25 reviewsBeautifully remodeled home in Historic Chestertown
Jun 27 – Jul 4
Other great vacation rentals in Chestertown
Home in Chestertown
5.0 out of 5 average rating, 14 reviewsDown by the River
Oct 13 – 20
Home in Chestertown
5.0 out of 5 average rating, 50 reviewsLovely, Recently-Renovated Home in Chestertown
Oct 22 – 29
Apartment in Chestertown
4.92 out of 5 average rating, 62 reviews1-br apt in downtown Chestertown
Apr 10 – 17
Home in Chestertown
5.0 out of 5 average rating, 23 reviewsMagnolia House ~Historic Downtown w/Private Garden
Oct 24 – 31
Home in Chestertown
5.0 out of 5 average rating, 19 reviewsIn Town Chestertown Rancher (1 Block to College)
Jun 4 – 11
Home in Chestertown
5.0 out of 5 average rating, 16 reviewsGoose Haven, new waterfront house on Fairlee Creek
Jun 21 – 28
Apartment in Chestertown
4.98 out of 5 average rating, 87 reviewsRIVER WATCH
Aug 16 – 23
Apartment in Rock Hall
4.96 out of 5 average rating, 47 reviewsBayside bungalow cottage by the sea
Aug 20 – 27
Home in Rock Hall
5.0 out of 5 average rating, 11 reviewsChesapeake Bay Retreat w/ Views!
Aug 13 – 20
Cottage in Betterton
4.8 out of 5 average rating, 51 reviewsCottage By the Chesapeake
May 13 – 20
Home in Chestertown
5.0 out of 5 average rating, 23 reviewsPrivate Cottage, Chestertown - "Cliff Pines"
Jul 23 – 30
Home in Greensboro
4.95 out of 5 average rating, 44 reviewsCozy 2 bedroom home on wooded private lane
Feb 5 – 12
Quick stats about vacation rentals in Chestertown
Total rentals | 50 properties |
---|---|
Wifi availability | 50 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 | 2.4K 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 30 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 30 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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