Holiday houses in Chestertown
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Top-rated accommodation in Chestertown
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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.
7–14 Aug
Apartment in Chestertown
4.97 out of 5 average rating, 188 reviewsQuiet escape in center of town
Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.
2–9 Aug
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.
28 Sep – 5 Oct
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Popular amenities for Chestertown accommodation
Other great accommodation in Chestertown
Casa particular in Chestertown
4.93 out of 5 average rating, 99 reviewsRed, White & Waterview Studio Apt with pool
27 Nov – 4 Dec
Home in Chestertown
4.96 out of 5 average rating, 69 reviewsCozy 3-bedroom home w/ screened in porch & firepit
15–22 Jan
Home in Chestertown
4.98 out of 5 average rating, 40 reviews2 Beds, 2.5 Baths, Perfect Downtown Location
8–15 May
Home in Chestertown
4.88 out of 5 average rating, 25 reviewsBeautifully remodeled home in Historic Chestertown
24 Jun – 1 Jul
Apartment in Chestertown
5.0 out of 5 average rating, 44 reviewsBright, new apartment in the heart of Chestertown
17–24 Jun
Home in Chestertown
5.0 out of 5 average rating, 23 reviews125 High - Luxury Historical Brick Victorian
5–12 Feb
Home in Chestertown
5.0 out of 5 average rating, 75 reviewsRiver front cottage with private dock & water fun
5–12 Apr
Home in Chestertown
4.93 out of 5 average rating, 28 reviewsHarbor View Haven | Waterfront w/ HOT TUB + Dock!
7–14 Oct
Home in Chestertown
5.0 out of 5 average rating, 35 reviewsWaterfront house with private dock & kayaks!
4–11 Dec
Home in Chestertown
5.0 out of 5 average rating, 14 reviewsDown by the River
14–21 Oct
Home in Chestertown
5.0 out of 5 average rating, 50 reviewsLovely, Recently-Renovated Home in Chestertown
22–29 Oct
Home in Chestertown
5.0 out of 5 average rating, 23 reviewsMagnolia House ~Historic Downtown w/Private Garden
18–25 Dec
Quick stats about accommodation in Chestertown
Total rentals | 50 properties |
---|---|
Wi-Fi availability | 50 properties include access to Wi-Fi |
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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