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.

Guest favorite

Farm stay in Chestertown

4.94 out of 5 average rating, 106 reviews

Outrange 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

$202 per night
Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 127 reviews

CHESAPEAKE 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

$170 per night
Guest favorite

Apartment in Chestertown

4.97 out of 5 average rating, 188 reviews

Quiet 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

$177 per night

Popular amenities for Kent County vacation rentals

Other great vacation rentals in Kent County

Guest favorite

Home in Chestertown

4.96 out of 5 average rating, 69 reviews

Cozy 3-bedroom home w/ screened in porch & firepit

Jan 15 – 22

$172 per night
Guest favorite

Home in Chestertown

4.98 out of 5 average rating, 40 reviews

2 Beds, 2.5 Baths, Perfect Downtown Location

May 8 – 15

$160 per night
Guest favorite

Guest suite in Chestertown

4.93 out of 5 average rating, 45 reviews

Historic Downtown Garden Oasis with Private Patio

Oct 7 – 14

$144 per night
Guest favorite

Apartment in Rock Hall

4.96 out of 5 average rating, 47 reviews

Bayside bungalow cottage by the sea

Aug 21 – 28

$125 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 35 reviews

Waterfront house with private dock & kayaks!

Dec 4 – 11

$215 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Apr 5 – 12

$450 per night
Guest favorite

Home in Chestertown

4.93 out of 5 average rating, 28 reviews

Harbor View Haven | Waterfront w/ HOT TUB + Dock!

Oct 7 – 14

$546 per night
Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 27 reviews

Eastern Neck Water Paradise w/Brick oven & Beach

Jan 28 – Feb 4

$709 per night
Superhost

Guesthouse in Centreville

4.83 out of 5 average rating, 71 reviews

Centreville Cottage

Sep 12 – 19

$133 per night
Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 11 reviews

Chesapeake Bay Retreat w/ Views!

Dec 12 – 19

$228 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 14 reviews

Down by the River

Oct 14 – 21

$700 per night
Guest favorite

Home in Chestertown

4.88 out of 5 average rating, 25 reviews

Beautifully remodeled home in Historic Chestertown

Jun 24 – Jul 1

$155 per night

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