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Vacation rentals in Chester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chester

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

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
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

Stay near Chester's top sights

Photo of Harris Crab House
Harris Crab House22 locals recommend
Photo of Fisherman's Inn Restaurant
Fisherman's Inn Restaurant27 locals recommend
Photo of Fisherman's Crab Deck
Fisherman's Crab Deck19 locals recommend
Photo of Bridges Restaurant
Bridges Restaurant48 locals recommend
Photo of Dunkin' Donuts
Dunkin' Donuts8 locals recommend
Photo of Annie's Paramount Steak & Seafood House
Annie's Paramount Steak & Seafood House8 locals recommend

Other great vacation rentals in Chester

Guesthouse in Chester
Waterfront Guest Cottage: Sunsets, Pool, Pier
$433 per night
Private room in Grasonville
Bay Bridge Retreat - 8 mins from the Bridge
$85 per night
Home in Chester
Chester Delight- Fireplace/Deck&Patio+fenced yard
$271 per night
Private room in Stevensville
Rustic & Elegant Private Bed & Bath
$118 per night
Private room in Chester
Tony's place
$125 per night
Home in Annapolis
Historic Downtown in-law suite
$120 per night
Bungalow in Chester
Historic Island Home
$250 per night
Rental unit in Grasonville
Halcyon house. Lovely views on MD eastern shore.
$182 per night
Houseboat in Grasonville
Cass-Away A Luxury Houseboat
$328 per night
Home in Stevensville
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
$203 per night
Guest suite in Stevensville
Kent Island Haven - A Waterfront Getaway
$200 per night
Rental unit in Stevensville
Kent Island Apartment W/ Attached Lounge!
$256 per night

Other types of stays on Airbnb

  1. Airbnb
  2. United States
  3. Maryland
  4. Queen Anne's County
  5. Chester