Chester Resorts

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Resorts in Chester

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$409 nightly
The price is $450 total per night
$450 total
Nov 16 - Nov 17
Total with taxes and fees
A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski Area.
Pool
Hot Tub
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
$172 nightly
The price is $189 total per night
$189 total
Oct 21 - Oct 22
Total with taxes and fees
Free Cancellation
Located in West Dover, Grand Summit Resort, A Vail Resorts Property is a 1-minute drive from Mount Snow and 7 minutes from Mount Snow Golf Course.
Spa
Free WiFi
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3 out of 5
5 Village Lodge Road Stratton VT
$164 nightly
The price is $180 total per night
$180 total
Oct 22 - Oct 23
Total with taxes and fees
When you stay at The Black Bear Lodge at Stratton Mountain Resort in Stratton, you'll be next to a golf course, just steps from Stratton Mountain Resort and Green Mountain National Forest.
Hot Tub
Breakfast included
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road Brownsville VT
$154 nightly
The price is $168 total per night
$168 total
Oct 26 - Oct 27
Total with taxes and fees
Free Cancellation
Located in Brownsville, Holiday Inn Club Vacations Mount Ascutney Resort by IHG is in a national park, within a 15-minute drive of American Precision Museum and Paradise Park.
Restaurant
Air conditioning
King with Bunk Bed- 2nd floor in Historic Inn

King with Bunk Bed- 2nd floor in Historic Inn

West Dover VT
$345 nightly
The price is $376 total per night
$376 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at this resort in West Dover, you'll be in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Mount Snow.
Pool
Air conditioning
Deluxe King Room w/pull-out love seat and fireplace

Deluxe King Room w/pull-out love seat and fireplace

Dover VT
$370 nightly
The price is $403 total per night
$403 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at this resort in West Dover, you'll be in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Mount Snow.
Pool
Hot Tub
Deluxe King Room w/fireplace and separate entrance

Deluxe King Room w/fireplace and separate entrance

West Dover VT
$372 nightly
The price is $405 total per night
$405 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at this resort in West Dover, you'll be in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Mount Snow.
Pool
Air conditioning
Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn

West Dover VT
$345 nightly
The price is $376 total per night
$376 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at this resort in West Dover, you'll be in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Mount Snow.
Pool
Air conditioning
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub

West Dover VT
$357 nightly
The price is $389 total per night
$389 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at this resort in West Dover, you'll be in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Mount Snow.
Pool
Air conditioning
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Dover VT
$396 nightly
The price is $432 total per night
$432 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at this resort in West Dover, you'll be in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Mount Snow.
Pool
Air conditioning
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance

Dover VT
$435 nightly
The price is $475 total per night
$475 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at this resort in West Dover, you'll be in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Mount Snow.
Pool
Air conditioning
Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn

West Dover VT
$344 nightly
The price is $375 total per night
$375 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at this resort in West Dover, you'll be in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Mount Snow.
Pool
Air conditioning
Don't see what you're looking for?
See all available properties in Chester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chester Resorts essential information

Accommodation
28 Resorts
Lowest Price
$168
Highest Price
$475
Popular accommodation
Woodstock Inn & Resort, Grand Summit Resort, A Vail Resorts Property, The Black Bear Lodge at Stratton Mountain Resort, Holiday Inn Club Vacations Mount Ascutney Resort by IHG, King with Bunk Bed- 2nd floor in Historic Inn, Deluxe King Room w/pull-out love seat and fireplace, Deluxe King Room w/fireplace and separate entrance, Deluxe 2xQueen- 2nd floor in Historic Inn, Luxury King Suite, Living Room w/sofa bed and jacuzzi tub, Deluxe King, Living Room w/sofa bed, bunk bed & fireplace, Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance, Deluxe 2xQueen in Historic Inn

Top Picks