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.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester
Guest favourite
Cottage in Saint Michaels
4.99 out of 5 average rating, 137 reviewsLa Casita on Harris Creek, St. Michaels
Aug. 12 – 19
$812 CAD per night
Guest favourite
Guesthouse in Easton
4.99 out of 5 average rating, 547 reviewsChill in The Crib! Easton, Maryland
Dec. 17 – 22
$219 CAD per night
Superhost
Apartment in Chester
4.93 out of 5 average rating, 15 reviewsCoastal Kent Narrows Home on Bay
Jul. 16 – 23
$454 CAD per night
Guest favourite
Home in Chester
5.0 out of 5 average rating, 15 reviews*Waterfront Sunset Bayview* sleeps 6
Oct. 13 – 20
$606 CAD per night
Guest favourite
Home in Stevensville
4.86 out of 5 average rating, 50 reviewsCheerful & Spacious Shore Life Beauty!
Mar. 6 – 13
$359 CAD per night
Guest favourite
Guesthouse in Stevensville
5.0 out of 5 average rating, 25 reviewsChesapeake Cottage
Aug. 6 – 13
$329 CAD per night
Guest favourite
Home in Chester
5.0 out of 5 average rating, 40 reviewsChester Delight- Fireplace/Deck&Patio+fenced yard
Sep. 20 – 27
$704 CAD per night
Guest favourite
Home in Stevensville
5.0 out of 5 average rating, 80 reviewsKent Island Waterfront Home with Amazing Sunsets
Jun. 4 – 11
$814 CAD per night
Destinations to explore
- Baltimore Vacation rentals
- Ocean City Vacation rentals
- Cape May Vacation rentals
- Wildwood Vacation rentals
- Rehoboth Beach Vacation rentals
- Arlington Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom