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Holiday 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
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bathroom
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.
Guest Suite in a Victorian on the Chester River
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bathroom
Guest Suite in a Victorian on the Chester RiverOur lovingly-restored Millington Manor is the original home of the local doctor, built in 1868. Our small town has a pizza/sub shop, liquor store as well as a restaurant that serves delicious lunch, dinner and has a nice wine selection. The two restaurants and liquor store are within a few minute's walking distance. We are a 15-minute ride to Chestertown, home of Washington College and host to wonderful restaurants, lovely shops, galleries and a theatre. Crumpton's auction is minutes away.
CHESAPEAKE SUNSETS
SUPERHOST
Entire residential home · 5 guests · 2 beds · 1 bathroom
CHESAPEAKE SUNSETSEscape 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 Tollchester Marina featuring live music, dining and its own beach or a private community boat ramp to launch your water toys. This 800 sq ft 2 bedroom 1 bath house is located on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.

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Popular amenities for Kent County holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Kent County

SUPERHOST
  1. Entire rental unit
  2. Chestertown
Carriage House Hideaway in Middle of Chestertown
$161 SGD per night
SUPERHOST
  1. Entire guest house
  2. Chestertown
Cozy Carriage House
$128 SGD per night
SUPERHOST
  1. Entire guest suite
  2. Chestertown
Beautiful Waterfront Chestertown Getaway
$133 SGD per night
SUPERHOST
  1. Entire residential home
  2. Rock Hall
Pirates Perch
$203 SGD per night
  1. Farm stay
  2. Chestertown
Blue Heron Farm Waterfront Chalet
$384 SGD per night
No reviews yet
  1. Entire residential home
  2. Earleville
Sassy on the Sassafras River
$135 SGD per night
SUPERHOST
  1. Entire cabin
  2. Chestertown
Rivershore Retreat
$390 SGD per night
SUPERHOST
  1. Entire residential home
  2. Chestertown
Wren Retweet- Country Estate in Center of C’Town
$311 SGD per night
SUPERHOST
  1. Entire residential home
  2. Kennedyville
Comfy and Cozy
$202 SGD per night
SUPERHOST
  1. Entire residential home
  2. Galena
Sweet and "Sassy"-4 Bedroom 2 Bath River Home
$269 SGD per night
  1. Entire residential home
  2. Rock Hall
Bayside Beach House
$269 SGD per night
  1. Entire cottage
  2. Galena
Tranquil and relaxing escape at Morton Hall
$173 SGD per night