Hotels in Chester
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Where to stay in Chester?
Fullerton Inn
Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (403)
8.2/10
Very Good
(403)
- Soak in small-town Vermont charm with free breakfast and staff that wins rave reviews.
The price is $129
$129
$141 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
9.2/10
Wonderful
(107)
- Cozy Chester retreat with historic charm and outdoor adventures await you.
The price is $232
$232
$253 total
includes taxes & fees
Dec 29 - Dec 30
The Hartness House
The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very Good, (329)
8.2/10
Very Good
(329)
- Historic Vermont inn near train station with trails nearby for adventurers.
The price is $183
$183
$202 total
includes taxes & fees
Dec 30 - Dec 31
Best Western Springfield Hotel
Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (806)
8.8/10
Excellent
(806)
- Experience a tranquil retreat with easy access to outdoor attractions and amenities.
The price is $152
$152
$167 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Inn at Weathersfield
The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
9.8/10
Exceptional
(70)
- Just steps from Vermont's North Springfield Lake, this charming inn offers breakfast and dining.
The price is $197
$197
$251 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (935)
8.8/10
Excellent
(935)
The price is $169
$169
$193 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Castle Hill Resort And Spa
Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (104)
9.0/10
Wonderful
(104)
The price is $299
$299
$326 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic Mountain
2.5 star property
Londonderry
8.2 out of 10, Very Good, (688)
8.2/10
Very Good
(688)
The price is $106
$106
$118 total
includes taxes & fees
Jan 25 - Jan 26, 2026
COHO Inn & Motor Lodge
COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (47)
9.4/10
Exceptional
(47)
- Experience Weston's charm at a motel with hiking trails and kayaking nearby.
The price is $163
$163
$178 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Rodeway Inn Bellows Falls
Rodeway Inn Bellows Falls
2.0 star property
Bellows Falls
6.2 out of 10, (288)
6.2/10
(288)
- Wake up to cozy Vermont charm minutes away from Bellows Falls Station.
The price is $116
$116
$127 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (113)
9.2/10
Wonderful
(113)
- Ski lodge retreat at Magic Mountain with spa services and seasonal outdoor pool.
The price is $179
$179
$197 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Harvest Barn Inn
Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
9.8/10
Exceptional
(244)
The price is $169
$169
$184 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Weston
The Weston
5.0 star property
Weston
10.0 out of 10, Exceptional, (9)
10/10
Exceptional
(9)
- Unwind at this Vermont guesthouse with a spa, garden, and nearby attractions.
The price is $450
$450
$491 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Main and Mountain Bar & Motel
Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (212)
9.6/10
Exceptional
(212)
- Downtown Ludlow charm with mountain resort minutes away and free shuttle service.
The price is $308
$308
$339 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Windham Hill Inn
Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very Good, (38)
8.4/10
Very Good
(38)
- Relax in a charming Vermont B&B with seasonal outdoor pool and snowy adventures.
The price is $189
$189
$206 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts Property
3.0 star property
Jackson Gore Base Area
8.6 out of 10, Excellent, (840)
8.6/10
Excellent
(840)
- Stay close to Okemo Mountain Resort with ski-in/ski-out access and two pools.
The price is $390
$390
$474 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Claremont Motor Lodge
Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (453)
8.8/10
Excellent
(453)
- Welcoming motel for New Hampshire explorers with attentive staff service.
The price is $105
$105
$114 total
includes taxes & fees
Dec 28 - Dec 29
Royal Inn Claremont
Royal Inn Claremont
2.0 star property
Claremont
6.6 out of 10, (318)
6.6/10
(318)
- Unwind along Claremont's scenic trails with free parking and WiFi at this cozy motel.
The price is $110
$110
$119 total
includes taxes & fees
Dec 28 - Dec 29
The Common Man Inn & Restaurant
The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (370)
9.6/10
Exceptional
(370)
- Unwind in a historic New Hampshire inn near the train station with a hot tub and dining.
The price is $151
$151
$164 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Echo Lake Inn
Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
8.6/10
Excellent
(98)
- Vermont countryside B&B close to Okemo Mountain Resort and Echo Lake.
The price is $291
$291
$318 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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.
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.
Budget hotels in Chester and vicinity
8.4 out of 10, Very Good, (1001)
8.4/10
Very Good
(1001)
The price is $94
$94
$103 total
includes taxes & fees
Dec 30 - Dec 31
9.4 out of 10, Exceptional, (327)
9.4/10
Exceptional
(327)
The price is $77
$77
$113 total
includes taxes & fees
Jan 4 - Jan 5, 2026
7.6 out of 10, Good, (1001)
7.6/10
Good
(1001)
The price is $78
$78
$86 total
includes taxes & fees
Dec 28 - Dec 29
9.6 out of 10, Exceptional, (549)
9.6/10
Exceptional
(549)
The price is $78
$78
$149 total
includes taxes & fees
Jan 6 - Jan 7, 2026
7.0 out of 10, Good, (1000)
7.0/10
Good
(1000)
The price is $84
$84
$91 total
includes taxes & fees
Dec 31 - Jan 1, 2026
8.8 out of 10, Excellent, (613)
8.8/10
Excellent
(613)
The price is $99
$99
$120 total
includes taxes & fees
Jan 13 - Jan 14, 2026
The Palmer House Resort, an Ascend Collection Hotel
The Palmer House Resort, an Ascend Collection Hotel3.0 star property
Manchester Center
8.4 out of 10, Very Good, (866)
8.4/10
Very Good
(866)
The price is $101
$101
$128 total
includes taxes & fees
Jan 19 - Jan 20, 2026
8.8 out of 10, Excellent, (453)
8.8/10
Excellent
(453)
The price is $105
$105
$114 total
includes taxes & fees
Dec 28 - Dec 29
9.0 out of 10, Wonderful, (406)
9.0/10
Wonderful
(406)
The price is $131
$131
$144 total
includes taxes & fees
Jan 27 - Jan 28, 2026
The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic Mountain2.5 star property
Londonderry
8.2 out of 10, Very Good, (688)
8.2/10
Very Good
(688)
The price is $106
$106
$118 total
includes taxes & fees
Jan 25 - Jan 26, 2026
7.4 out of 10, Good, (475)
7.4/10
Good
(475)
The price is $110
$110
$121 total
includes taxes & fees
Dec 29 - Dec 30
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-912.5 star property
Brattleboro
8.6 out of 10, Excellent, (746)
8.6/10
Excellent
(746)
The price is $120
$120
$132 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection Hotel2.5 star property
Keene
8.4 out of 10, Very Good, (968)
8.4/10
Very Good
(968)
The price is $124
$124
$135 total
includes taxes & fees
Dec 28 - Dec 29
8.4 out of 10, Very Good, (839)
8.4/10
Very Good
(839)
The price is $117
$117
$129 total
includes taxes & fees
Dec 28 - Dec 29
9.6 out of 10, Exceptional, (156)
9.6/10
Exceptional
(156)
The price is $161
$161
$179 total
includes taxes & fees
Dec 30 - Dec 31
8.2 out of 10, Very Good, (403)
8.2/10
Very Good
(403)
The price is $129
$129
$141 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHG3.0 star property
Brownsville
9.0 out of 10, Wonderful, (780)
9.0/10
Wonderful
(780)
The price is $129
$129
$157 total
includes taxes & fees
Jan 5 - Jan 6, 2026
9.8 out of 10, Exceptional, (15)
9.8/10
Exceptional
(15)
The price is $129
$129
$141 total
includes taxes & fees
Dec 30 - Dec 31
Hampton Inn and Suites Manchester
Hampton Inn and Suites Manchester2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1003)
9.6/10
Exceptional
(1003)
The price is $130
$130
$143 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.6 out of 10, Exceptional, (165)
9.6/10
Exceptional
(165)
The price is $142
$142
$154 total
includes taxes & fees
Dec 29 - Dec 30
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.
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.
Go beyond your typical stay in Chester
Pet friendly
Family friendly
Cottage
When is the best time to visit Chester?
When is the best time to visit Chester?Our prices for hotels in Chester are cheapest in December
When is the best time to visit Chester?
When is the best time to visit Chester?
Our prices for hotels in Chester are cheapest in December
Price trends for hotels in Chester
Pricing is based on two traveler single night rates
Currently viewing crowd sizes and weather for December.
Typical weather for Chester
December
High crowds
High 1°C / low -6°C. Snow likely.
View properties in December 1°
December, High crowds, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
-2°
January, High crowds, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
-11°
0°
February, High crowds, average high temperature 0 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
-10°
4°
March, Moderate crowds, average high temperature 4 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
12°
April, Low crowds, average high temperature 12 degrees Celsius, average low temperature 1 degrees Celsius. Cloudy most days.
1°
19°
May, Low crowds, average high temperature 19 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
23°
June, Low crowds, average high temperature 23 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
27°
July, Moderate crowds, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
26°
August, Moderate crowds, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
22°
September, Moderate crowds, average high temperature 22 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
15°
October, High crowds, average high temperature 15 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
5°
7°
November, Low crowds, average high temperature 7 degrees Celsius, average low temperature -2 degrees Celsius. Partly sunny.
-2°
Monthly weather averages (˚C)
Top neighborhoods in Chester
Chester Depot
The Chester Depot neighborhood has lots to see including DaVallia Art & Accents and Bonnie's Bundles Dolls.
Top landmarks in Chester
Learn more about Chester
Notable for its skiing, Chester features attractions such as Bonnie's Bundles Dolls and DaVallia Art & Accents. Visitors speak highly of this relaxing city's coffeehouses and small-town setting.
Check out reviews of Chester hotels guests love
Comfort Inn & Suites Brattleboro I-91
10/10 Excellent
"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
Kimpton Taconic Hotel by IHG
10/10 Excellent
"10/10 Perfect Stay.
So accommodating and kind staff. "
On The River Inn
10/10 Excellent
"Rearaurant staff was top notch. "
The Covered Bridge Inn
10/10 Excellent
"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
Woodstock Inn & Resort
10/10 Excellent
"Luxurious and friendly resort! Loved it"
The Black Bear Lodge at Stratton Mountain Resort
10/10 Excellent
"Place definitely needs some updating but it was clean and the staff was great!"
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
10/10 Excellent
"Super responsive staff, great accomodations "
Hampton Inn and Suites Manchester
10/10 Excellent
"Room was spotless. Staff was friendly."
The Jackson
10/10 Excellent
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
Frequently asked questions
What accommodations do travelers recommend in Chester?
Stone Hearth Inn and Eatery and Fullerton Inn are a couple of accommodations that are popular with guests.
Can I book a refundable hotel in Chester?
If you want the flexibility to change your plans to Chester, most properties provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Chester if I want a vacation home instead of a hotel?
If you want a good alternative to a hotel, browse our selection of 34 vacation homes. You also might want to book one of 7 cottages or 9 cabins.
What will the weather in Chester be like during my vacation?
The warmest months in Chester are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 25°F. The rainiest months are October and July.
Why should I book my Chester accommodation with Hotels.com?
There are plenty of reasons to book your Chester travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.