Book 2 Star Hotels in Chester
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Chester 2 Stars Hotels

Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
8.76 mi from city center
$144 nightly
The price is $157 total per night
$157 total
Dec 15 - Dec 16
Total with taxes and fees
At Pointe at Castle Hill Resort, guests enjoy a full-service spa, an indoor pool, and a gym. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with luggage storage and concierge services. Other amenities at this spa hotel include free WiFi in public areas, a hot tub, and meeting rooms.
Pool
Hot Tub

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road Brownsville VT
15.35 mi from city center
$134 nightly
The price is $146 total per night
$146 total
Dec 18 - Dec 19
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG features an indoor pool, an outdoor tennis court, and meeting rooms. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include conference space, a business center, and a seasonal outdoor pool.

The Palmer House Resort, an Ascend Collection Hotel
5383 Main St Manchester Center VT
Free Cancellation
23.5 mi from city center
$122 nightly
The price is $134 total per night
$134 total
Dec 21 - Dec 22
Total with taxes and fees
Guests staying at The Palmer House Resort, an Ascend Collection Hotel enjoy access to a golf course, an indoor pool, and outdoor tennis courts. A stay here includes free parking. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Other amenities at this golf hotel include free WiFi in public areas, a hot tub, and a seasonal outdoor pool.

Hampton Inn and Suites Manchester
4519 Main St Manchester Center VT
Free Cancellation
Reserve now, pay when you stay
24.29 mi from city center
$130 nightly
The price is $143 total per night
$143 total
Dec 14 - Dec 15
Total with taxes and fees
At Hampton Inn and Suites Manchester, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. If you drive, take advantage of free parking. The front desk is staffed 24 hours a day to help with securing valuables and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a hot tub, a business center, and coffee/tea in a common area.

Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Free Cancellation
24.85 mi from city center
$204 nightly
The price is $225 total per night
$225 total
Dec 14 - Dec 15
Total with taxes and fees
Kimpton Taconic Hotel by IHG offers a 24-hour gym, meeting rooms, and conference space. The 24-hour front desk has staff standing by to help with tours or tickets, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this golf hotel include a seasonal outdoor pool, coffee/tea in a common area, and free use of bicycles.
Pool
Pet friendly

Woodstock Inn & Resort
Fourteen The Green Woodstock VT
25.17 mi from city center
$379 nightly
The price is $417 total per night
$417 total
Dec 15 - Dec 16
Total with taxes and fees
Guests of Woodstock Inn & Resort have access to a golf course, a full-service spa, and an indoor pool. Free valet parking is included with your stay. The front desk is staffed 24/7 to help with concierge services, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury resort include a gym, 2 hot tubs, and a sauna.
Pool
Hot Tub

The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Free Cancellation
Reserve now, pay when you stay
25 mi from city center
$223 nightly
The price is $245 total per night
$245 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Guests of The Equinox Golf Resort & Spa have access to a golf course, a full-service spa, and an indoor pool. Free parking is included with your stay. Front-desk staff can answer questions 24/7, and assist with concierge services, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a 24-hour gym, a sauna, and outdoor tennis courts.
Pool
Hot Tub

The Shire Woodstock
46 Pleasant St. Woodstock VT
Free Cancellation
Reserve now, pay when you stay
25.48 mi from city center
$158 nightly
The price is $174 total per night
$174 total
Dec 18 - Dec 19
Total with taxes and fees
The Shire Woodstock features free WiFi in public areas, coffee in a common area, and free use of bicycles. You can take advantage of free parking if you drive. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include a garden and a picnic area.
Pet friendly
Parking included

Mount Snow Grand Summit Resort
89 Grand Summit Way West Dover VT
25.45 mi from city center
$243 nightly
The price is $268 total per night
$268 total
Dec 15 - Dec 16
Total with taxes and fees
Guests of Mount Snow Grand Summit Resort have access to ski-in/ski-out access, a full-service spa, and an outdoor pool. If you drive, self parking is USD 5.00 per night, and there's also a free area shuttle. Front-desk staff can answer questions 24/7, and assist with luggage storage, tours or tickets, and securing valuables. Other amenities at this ski resort include a gym, 2 hot tubs, and a sauna.
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 hotels essential information
Accommodation | 3,061 hotels |
|---|---|
Lowest Price | $134 |
Highest Price | $417 |
Popular hotels | Woodstock Inn & Resort, The Shire Woodstock, The Equinox Golf Resort & Spa, Kimpton Taconic Hotel by IHG, Pointe at Castle Hill Resort, Hampton Inn and Suites Manchester, The Palmer House Resort, an Ascend Collection Hotel, Holiday Inn Club Vacations Mount Ascutney Resort by IHG, Mount Snow Grand Summit Resort |
Recent Reviews

Hampton Inn and Suites Manchester
5/5 Excellent
"all is well"
A verified traveler stayed at Hampton Inn and Suites Manchester
Posted 4 days ago


