Vacation rentals in Chestertown
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Top-rated vacation rentals in Chestertown
Guests agree: these stays 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, 150 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
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Popular amenities for Chestertown vacation rentals
Other great vacation rentals in Chestertown
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
Home in Chestertown
5.0 out of 5 average rating, 23 reviews125 High - Luxury Historical Brick Victorian
Aug. 6 – 13
Home in Chestertown
5.0 out of 5 average rating, 75 reviewsRiver front cottage with private dock & water fun
Apr. 5 – 12
Home in Chestertown
4.93 out of 5 average rating, 28 reviewsHarbor View Haven | Waterfront w/ HOT TUB + Dock!
Oct. 7 – 14
Home in Chestertown
5.0 out of 5 average rating, 35 reviewsWaterfront house with private dock & kayaks!
Dec. 4 – 11
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
Home in Chestertown
5.0 out of 5 average rating, 23 reviewsMagnolia House ~Historic Downtown w/Private Garden
Dec. 18 – 25
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 |
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