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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.

Home in Chester
Chester Delight- Fireplace/Deck&Patio+fenced yard
Welcome to Chester Delight! Recently remodeled, with a refined appearance and all new furniture our Airbnb offers a home-like experience. Relax at the fireplace, watch TV with a high-quality sound, cook a meal in the fully equipped kitchen and dine. Spend quality time at our outdoor retreat. The house is close to popular restaurants, marinas, wedding venues, golf courses, wineries, and parks. It’s a perfect base to explore Kent Island. Enjoy this stylish house at the centrally located place.
$236 per night
Private room in Chester
Kent Island Waterfront Suite 2
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, Jacuzzi 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 reservation.
$190 per night
Rental unit in Chester
Cozy Waterfront Apartment Kent Island
*We live on the property* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy this clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. Plus an easy to assemble blow up air mattress to sleep an additional two. WiFi included. Private porch to sit & enjoy beautiful water views!
$110 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 Annie's Paramount Steak & Seafood House
Annie's Paramount Steak & Seafood House8 locals recommend
Photo of Dunkin' Donuts
Dunkin' Donuts8 locals recommend

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❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
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Home in Kent Narrows
Chester Riverfront At Kent Narrows
$288 per night
Home in Chester
Waterfront Farmhouse Meets Modern Luxury
$556 per night
Rental unit in Stevensville
Kent Island Apartment W/ Attached Lounge!
$191 per night
Bungalow in Chester
Historic Island Home
$230 per night
Private room in Chester
Tony's place
$125 per night
Home in Stevensville
Relax on Kent Island in 3 Bedroom Home w/Waterview
$143 per night
Private room in Annapolis
Chesapeake Mornings
$50 per night
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
$152 per night
Home in Annapolis
Historic Downtown in-law suite
$117 per night
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