Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Private room in Chester

Kent Island Waterfront Suite I

One of 2 private suites available on second floor with sweeping views of Crab Alley Bay on Kent Island. Wake up to an amazing sunrise, relax and watch the boats and wildlife from your room featuring a wall of windows. The bath features, Oversized tub and steam shower. Located just minutes to the Kent Narrows area. WIFI for each room. Shared common areas that include sitting room at entrance of upper level and kitchenette with laundry. ID's must be verified through AIRBNB prior to booking.

$190 per night

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Home in Chester

Waterfront Paradise to Work or Rest

Retreat with family, friends or team member to an idyllic waterfront house that faces west. That means, you will see the most beautiful sunsets of the Chesapeake Bay from the living area, the deck or the pier while relaxing. Open concept kitchen connected to the social area of a fully renovated home. Very well, equipped kitchen with fancy details. The huge backyard offer plenty of room for having fun outside doing, a fire pit or playing outdoor games. Two TV rooms. This is a paradise!

$477 per night

Home in Chester

Waterfront Farmhouse Meets Modern Luxury

Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

$716 per night

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