Vacation rentals in Kingstown
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Top-rated vacation rentals in Kingstown
Guests agree: these stays are highly rated for location, cleanliness, and more.
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.
Aug 2 – 9
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.
Sep 28 – Oct 5
Guest suite in Chestertown
4.99 out of 5 average rating, 126 reviewsChestertown - Eastern Shore Getaway
"A little slice of Americana" (commented one of our guests) This century-old three-story home is in the beautiful historic district of Chestertown, which sits on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue.
Aug 19 – 26
Vacation rentals for every style
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Popular amenities for Kingstown vacation rentals
Other great vacation rentals in Kingstown
Guest suite in Chestertown
4.93 out of 5 average rating, 45 reviewsHistoric Downtown Garden Oasis with Private Patio
Oct 7 – 14
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
4.96 out of 5 average rating, 69 reviewsCozy 3-bedroom home w/ screened in porch & firepit
Jan 15 – 22
Home in Chestertown
4.98 out of 5 average rating, 40 reviews2 Beds, 2.5 Baths, Perfect Downtown Location
May 8 – 15
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, 23 reviews125 High - Luxury Historical Brick Victorian
Feb 5 – 12
Home in Chestertown
5.0 out of 5 average rating, 14 reviewsDown by the River
Oct 14 – 21
Apartment in Chestertown
5.0 out of 5 average rating, 44 reviewsBright, new apartment in the heart of Chestertown
Jun 17 – 24
Home in Chestertown
4.88 out of 5 average rating, 25 reviewsBeautifully remodeled home in Historic Chestertown
Jun 24 – Jul 1
Home in Chestertown
5.0 out of 5 average rating, 23 reviewsMagnolia House ~Historic Downtown w/Private Garden
Dec 18 – 25
Home in Chestertown
5.0 out of 5 average rating, 19 reviewsIn Town Chestertown Rancher (1 Block to College)
Jun 5 – 12
Apartment in Chestertown
4.92 out of 5 average rating, 62 reviews1-br apt in downtown Chestertown
Jun 10 – 17
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