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Cheap Chester Hotels
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$419 nightly
The price is $461 total per night
$461 total
Dec 18 - Dec 19
Total with taxes and fees
25.17 mi from city center
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
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$177 nightly
The price is $193 total per night
$193 total
Dec 18 - Dec 19
Total with taxes and fees
8.76 mi from city center
With a stay at Pointe at Castle Hill Resort in Cavendish, you'll be near ski lifts, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School for the Arts and Crafts.
Pool
Hot Tub
The Shire Woodstock
46 Pleasant St. Woodstock VT
$156 nightly
The price is $172 total per night
$172 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
25.48 mi from city center
Located in Woodstock, The Shire Woodstock is on a river, within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee Health Center.
Pet friendly
Parking included
Mount Snow Grand Summit Resort
89 Grand Summit Way West Dover VT
$251 nightly
The price is $276 total per night
$276 total
Dec 18 - Dec 19
Total with taxes and fees
25.44 mi from city center
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.
Pool
Hot Tub
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
$229 nightly
The price is $252 total per night
$252 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
25 mi from city center
With a stay at The Equinox Golf Resort & Spa in Manchester (Manchester Village Historic District), you'll be steps from Green Mountain National Forest and Golf Club at Equinox.
Pool
Hot Tub
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
$196 nightly
The price is $216 total per night
$216 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
24.85 mi from city center
With a stay at Kimpton Taconic Hotel by IHG in Manchester (Manchester Village Historic District), you'll be steps from Green Mountain National Forest and 5 minutes by foot from American Museum of Fly Fishing.
Pool
Pet friendly
Hampton Inn and Suites Manchester
4519 Main St Manchester Center VT
$147 nightly
The price is $161 total per night
$161 total
Dec 23 - Dec 24
Total with taxes and fees
24.29 mi from city center
A stay at Hampton Inn and Suites Manchester places you in the heart of Manchester Center, steps from Green Mountain National Forest and 8 minutes by foot from Manchester Designer Outlets.
Pool
Hot Tub
The Palmer House Resort, an Ascend Collection Hotel
5383 Main St Manchester Center VT
$116 nightly
The price is $128 total per night
$128 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Free Cancellation
23.5 mi from city center
Centrally located in Manchester Center, The Palmer House Resort, an Ascend Collection Hotel is within a 15-minute walk of Lye Brook Falls and Manchester Designer Outlets.
Pool
Hot Tub
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road Brownsville VT
$139 nightly
The price is $152 total per night
$152 total
Dec 18 - Dec 19
Total with taxes and fees
Free Cancellation
15.35 mi from city center
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.
Pool
Restaurant
The Covered Bridge Inn
1043 Putney Road Brattleboro VT
$90 nightly
The price is $99 total per night
$99 total
Dec 18 - Dec 19
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
26.33 mi from city center
With a stay at The Covered Bridge Inn in Brattleboro, you'll be within a 10-minute walk of Brattleboro Bowl and United States Navy Seabee Bridge.
Parking included
Free WiFi
The Black Bear Lodge at Stratton Mountain Resort
5 Village Lodge Road Stratton VT
$204 nightly
The price is $224 total per night
$224 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
18.67 mi from city center
When you stay at The Black Bear Lodge at Stratton Mountain Resort in Stratton, you'll be next to a golf course, within a 5-minute walk of Stratton Mountain Resort and Green Mountain National Forest.
Hot Tub
Breakfast included
Jackson Gore Village
111 Jackson Gore Road Ludlow VT
$395 nightly
The price is $434 total per night
$434 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
12.62 mi from city center
With a stay at Jackson Gore Village, A Vail Resorts Property in Ludlow (Jackson Gore Base Area), you'll be within a 5-minute drive of Okemo Mountain Resort and Jackson Gore Parking.
Pool
Hot Tub
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.
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Chester hotels essential information
Accommodation | 3,055 hotels |
|---|---|
Lowest Price | $99 |
Highest Price | $461 |
Popular hotels | Woodstock Inn & Resort, Pointe at Castle Hill Resort, The Shire Woodstock, Mount Snow Grand Summit Resort, The Equinox Golf Resort & Spa, Kimpton Taconic Hotel by IHG, Hampton Inn and Suites Manchester, The Palmer House Resort, an Ascend Collection Hotel, Holiday Inn Club Vacations Mount Ascutney Resort by IHG, The Covered Bridge Inn, The Black Bear Lodge at Stratton Mountain Resort, Jackson Gore Village |
Most Recent Chester Hotel Reviews
Kimpton Taconic Hotel by IHG
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Experience was flawless from Check-In to Checking Out 👌🥰 The Staff was absolutely delightful - attentive , professional, so helpful and the Grouse Staff was equally outstanding - Bartender, and special mention for Chef Jeffery, and Servers Aria and Bean. We definitely plan to stay here again on our next visit to Manchester 👌❣️"
A verified traveler stayed at Kimpton Taconic Hotel by IHG
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