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Vacation rentals in Kent County

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Top-rated holiday rentals in Kent County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Home Farm Retreat
Farm stay · 2 guests · 1 bed · 1.5 baths

Home Farm RetreatIdeally situated well off the road in the middle of a working farm yet close to town for shopping and dining. It is a great retreat for a writer, a painter or a musician space with enough space to create. Private key code for access. Near marinas, parks, and charming Eastern Shore villages. Killer sunset views. Pet friendly. Out the door for wonderful and challenging country road bike rides with little to no traffic. A large fire pit and a private sitting room/gathering space.

Sunview Cottage on Chesapeake Bay
SUPERHOST
Entire cottage · 4 guests · 3 beds · 1 bath

Sunview Cottage on Chesapeake BaySunview is ideal for our times. Beautiful, in a natural setting, and clean. Modern, Cozy 2-Bedroom Cathedral-Ceiling Cottage with Central AC and Heat, Electric Fireplace, & Loft. Views of the Chesapeake Bay and sunsets from the house & wraparound deck. Perfect destination for a getaway with friends and family. Located in the scenic, serene environs of the Eastern Shore of Maryland in Tolchester. 20 mins. from Chestertown and 10 mins. from Rock Hall.

Cottage by the Chesapeake
Entire cottage · 6 guests · 3 beds · 1 bath

Cottage by the ChesapeakeThis updated cottage sits on a spacious private lot with views of mature trees and is a short walk to the beach! A darling front screened-in porch, with lots of space to dust off your beach sand. A side entrance with a quaint deck and a back deck entrance that faces a tranquil setting. The community of Betterton offers tennis courts, covered outside picnic tables with grills, a brand new playground, and of course...THE BEACH!

Holiday rentals for every style

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Popular amenities for Kent County holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Kent County

SUPERHOST
  1. Entire house
  2. Galena
Sweet and "Sassy"-4 Bedroom 2 Bath River Home
$258 AUD per night
$258.00 AUD total
SUPERHOST
  1. Private room
  2. Millington
Guest Suite in a Victorian on the Chester River
$74 AUD per night
$74.00 AUD total
  1. Entire cottage
  2. Galena
Tranquil and relaxing escape at Morton Hall
$170 AUD per night
$170.00 AUD total
SUPERHOST
  1. Entire guest suite
  2. Chestertown
Beautiful Waterfront Chestertown Getaway
$133 AUD per night
$133.00 AUD total
SUPERHOST
  1. Entire apartment
  2. Chestertown
Carriage House Hideaway in Middle of Chestertown
$131 AUD per night
$131.00 AUD total
SUPERHOST
  1. Entire house
  2. Rock Hall
Pirates Perch
$200 AUD per night
$200.00 AUD total
  1. Entire apartment
  2. Chestertown
The Bittersweet
$113 AUD per night
SUPERHOST
  1. Campervan/RV
  2. Chestertown
Cozy Airstream on a beautiful horse farm
$139 AUD per night
  1. Entire apartment
  2. Chestertown
Downtown Studio Apartment
$163 AUD per night
$163.00 AUD total
  1. Entire house
  2. Chestertown
Newly-Renovated Chestertown Charmer
$113 AUD per night
SUPERHOST
  1. Entire house
  2. Chestertown
CHESAPEAKE SUNSETS
$350 AUD per night
$350.00 AUD total
SUPERHOST
  1. Entire house
  2. Chestertown
Wren Retweet- Country Estate in Center of C’Town
$301 AUD per night
$301.00 AUD total