
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
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

Home in Chester
5 out of 5 average rating, 6 reviewsBright and spacious 3 bed/3 bath
Top guest favourite

Apartment in Springfield
5 out of 5 average rating, 5 reviewsSunny, serene, second floor
Guest favourite

Home in Chester
5 out of 5 average rating, 24 reviewsSerenity Awaits Peaceful Getaway on 6 acres + view
Top guest favourite

Home in Chester
5 out of 5 average rating, 91 reviewsHistoric Grist Mill in Scenic Chester, VT!
Top guest favourite

Private room in Bellows Falls
4.97 out of 5 average rating, 63 reviewsOld Victorian Charms and comfort
Guest favourite

Home in Baltimore
5 out of 5 average rating, 6 reviewsTarbell Farm on the hill top

Apartment in Chester
4.72 out of 5 average rating, 57 reviewsCharming 2 Bdrm near Skiing and Village Green

Home in Chester
4.8 out of 5 average rating, 5 reviewsCharming Victorian Farmhouse
Quick stats about vacation rentals in Chester
Total rentals
90 properties
Nightly prices starting at
$82 CAD before taxes and fees
Total number of reviews
3.6K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
- Boston Vacation rentals
- Hudson Valley Vacation rentals
- Montreal Vacation rentals
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Pocono Mountains Vacation rentals
- Jersey Shore Vacation rentals
- Québec City Vacation rentals
- Philadelphia 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
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- The Shattuck Golf Club
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Bromley Mountain Ski Resort
- Clarksburg State Park
- Bretwood Golf Course
- Baker Hill Golf Club
- Fox Run Golf Club
- Brattleboro Ski Hill
- Hooper Golf Course
- Crotched Mountain Ski and Ride
- Lucky Bugger Vineyard & Winery
- Cozy Cottages & Otter Valley Winery