Vacation rentals in Kent County
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Top-rated vacation rentals in Kent County
Guests agree: these stays are highly rated for location, cleanliness, and more.
Farm stay in Chestertown
4.94 out of 5 average rating, 106 reviewsOutrange at Blue Heron Farm
Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.
Feb 2 – 9
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 7 – 14
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
Vacation rentals for every style
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Popular amenities for Kent County vacation rentals
Other great vacation rentals in Kent County
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
Guest suite in Chestertown
4.93 out of 5 average rating, 45 reviewsHistoric Downtown Garden Oasis with Private Patio
Oct 7 – 14
Apartment in Rock Hall
4.96 out of 5 average rating, 47 reviewsBayside bungalow cottage by the sea
Aug 21 – 28
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, 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 Rock Hall
5.0 out of 5 average rating, 27 reviewsEastern Neck Water Paradise w/Brick oven & Beach
Jan 28 – Feb 4
Guesthouse in Centreville
4.83 out of 5 average rating, 71 reviewsCentreville Cottage
Sep 12 – 19
Home in Rock Hall
5.0 out of 5 average rating, 11 reviewsChesapeake Bay Retreat w/ Views!
Dec 12 – 19
Home in Chestertown
5.0 out of 5 average rating, 14 reviewsDown by the River
Oct 14 – 21
Home in Chestertown
4.88 out of 5 average rating, 25 reviewsBeautifully remodeled home in Historic Chestertown
Jun 24 – Jul 1
Destinations to explore
- Rentals with a washer and dryer Kent County
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