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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.

Newly-Renovated Chestertown Charmer
SUPERHOST
Entire residential home · 4 guests · 1 bed · 1 bath
Newly-Renovated Chestertown CharmerWelcome to charming Chestertown. This newly-renovated one-bedroom home is located in downtown Chestertown and is walkable to many restaurants, shops, and the water. Relax in this cozy space with all-new furniture and kitchen amenities. Enjoy the deck in the back with gas fireplace and grill. This home is perfect to enjoy all the spectacular aspects of small town living.
Beautiful Waterfront Chestertown Getaway
SUPERHOST
Entire guest suite · 2 guests · 2 beds · 1 bath
Beautiful Waterfront Chestertown GetawayLovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.
The Tree House in Chestertown
SUPERHOST
Entire rental unit · 1 guest · 1 bed · 1 bath
The Tree House in ChestertownLight-filled 1-bedroom for 2 guests is located near downtown historic Chestertown, Washington College, the Hospital & Heron Point. Three blocks to Fountain Park. Available as a monthly rental for one person. Kitchen, Dining, Living Room combo. Full Bath with Shower & Tub. Queen-size MacyBed by Serta Resort. Ideal for enjoying this historic, artistic town on Maryland's Eastern Shore. Located on the 2nd Floor of a historic Victorian.

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Other great vacation rentals in Kingstown

SUPERHOST
  1. Entire rental unit
Downtown Studio Apartment
SUPERHOST
  1. Entire cabin
Rivershore Retreat
SUPERHOST
  1. Entire rental unit
1-br apt in downtown Chestertown
SUPERHOST
  1. Entire guesthouse
Cozy Carriage House
SUPERHOST
  1. Private room
Chestertown - Eastern Shore Getaway
SUPERHOST
  1. Entire residential home
Merry Manor Pet Friendly Home
SUPERHOST
  1. Entire cottage
Quiet Cottage on Heron Pond
SUPERHOST
  1. Entire residential home
Wren Retweet- Country Estate in Center of C’Town
SUPERHOST
  1. Entire rental unit
RIVER WATCH
SUPERHOST
  1. Entire residential home
Waterfront w/Pier &Walking Distance to Chestertown
SUPERHOST
  1. Private room
Private Room w/bath: Walk to Washington College
SUPERHOST
  1. Entire residential home
River front cottage with private dock & water fun