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

Tonight
Jan 16 - Jan 17
Tomorrow
Jan 17 - Jan 18
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

Where to stay in Chester?

Garden
Fullerton Inn
Fullerton Inn
2.5 star property
Chester Depot
8.0 out of 10, Very Good, (409 reviews)
  • cleanliness
    Soak in small-town Vermont charm with free breakfast and staff that wins rave reviews.
The price is $129
$141 total
includes taxes & fees
Jan 20 - Jan 21
Fullerton Inn
Front of property
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (109 reviews)
  • cleanliness
    Cozy Chester retreat with historic charm and outdoor adventures await you.
The price is $282
$307 total
includes taxes & fees
Jan 29 - Jan 30
Stone Hearth Inn and Eatery
Lobby sitting area
The Hartness House
The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very Good, (331 reviews)
  • cleanliness
    Historic Vermont inn near train station with trails nearby for adventurers.
The price is $196
$215 total
includes taxes & fees
Feb 12 - Feb 13
The Hartness House
Exterior
Best Western Springfield Hotel
Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (813 reviews)
  • cleanliness
    Experience a tranquil retreat with easy access to outdoor attractions and amenities.
The price is $152
$167 total
includes taxes & fees
Jan 22 - Jan 23
Best Western Springfield Hotel
Interior
The Inn at Weathersfield
The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70 reviews)
  • cleanliness
    Just steps from Vermont's North Springfield Lake, this charming inn offers breakfast and dining.
The price is $197
$251 total
includes taxes & fees
Jan 19 - Jan 20
The Inn at Weathersfield
Front of property
Castle Hill Resort And Spa
Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (105 reviews)
The price is $219
$239 total
includes taxes & fees
Jan 25 - Jan 26
Castle Hill Resort And Spa
Sauna, aromatherapy, hot stone massages, deep-tissue massages
Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (955 reviews)
The price is $189
$215 total
includes taxes & fees
Jan 19 - Jan 20
Pointe at Castle Hill Resort
Restaurant
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, (689 reviews)
The price is $124
$137 total
includes taxes & fees
Jan 19 - Jan 20
The Upper Pass Lodge at Magic Mountain
Kayaking
Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (113 reviews)
  • cleanliness
    Ski lodge retreat at Magic Mountain with spa services and seasonal outdoor pool.
The price is $179
$197 total
includes taxes & fees
Jan 21 - Jan 22
Blue Gentian Lodge at Magic Mountain
Front of property
COHO Inn & Motor Lodge
COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (51 reviews)
  • cleanliness
    Experience Weston's charm at a motel with hiking trails and kayaking nearby.
The price is $160
$175 total
includes taxes & fees
Jan 20 - Jan 21
COHO Inn & Motor Lodge
Breakfast area
Rodeway Inn Bellows Falls
Rodeway Inn Bellows Falls
2.0 star property
Bellows Falls
6.2 out of 10, (288 reviews)
  • cleanliness
    Wake up to cozy Vermont charm minutes away from Bellows Falls Station.
The price is $110
$120 total
includes taxes & fees
Feb 15 - Feb 16
Rodeway Inn Bellows Falls
Porch
Harvest Barn Inn
Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (245 reviews)
The price is $169
$184 total
includes taxes & fees
Jan 26 - Jan 27
Harvest Barn Inn
Front of property
The Weston
The Weston
5.0 star property
Weston
10.0 out of 10, Exceptional, (9 reviews)
  • cleanliness
    Unwind at this Vermont guesthouse with a spa, garden, and nearby attractions.
The price is $405
$441 total
includes taxes & fees
Jan 29 - Jan 30
The Weston
Front of property - evening/night
Main and Mountain Bar & Motel
Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (214 reviews)
  • cleanliness
    Downtown Ludlow charm with mountain resort minutes away and free shuttle service.
The price is $308
$339 total
includes taxes & fees
Jan 26 - Jan 27
Main and Mountain Bar & Motel
Room, 1 Queen Bed, Garden View | Mountain view
Windham Hill Inn
Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very Good, (38 reviews)
  • cleanliness
    Relax in a charming Vermont B&B with seasonal outdoor pool and snowy adventures.
The price is $210
$229 total
includes taxes & fees
Jan 19 - Jan 20
Windham Hill Inn
Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Premium bedding, in-room safe, individually decorated
Claremont Motor Lodge
Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (458 reviews)
  • cleanliness
    Welcoming motel for New Hampshire explorers with attentive staff service.
The price is $110
$119 total
includes taxes & fees
Jan 19 - Jan 20
Claremont Motor Lodge
Property entrance
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, (844 reviews)
  • cleanliness
    Stay close to Okemo Mountain Resort with ski-in/ski-out access and two pools.
The price is $393
$478 total
includes taxes & fees
Jan 22 - Jan 23
Jackson Gore Village, A Vail Resorts Property
Standard Room, 2 Double Beds | Desk, blackout drapes, iron/ironing board, free WiFi
Royal Inn Claremont
Royal Inn Claremont
2.0 star property
Claremont
6.6 out of 10, (318 reviews)
  • cleanliness
    Unwind along Claremont's scenic trails with free parking and WiFi at this cozy motel.
The price is $99
$107 total
includes taxes & fees
Jan 18 - Jan 19
Royal Inn Claremont
Exterior
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (782 reviews)
  • cleanliness
    Mountain escape offering serene atmosphere and seasonal outdoor pools in Brownsville.
The price is $149
$179 total
includes taxes & fees
Jan 26 - Jan 27
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Exterior
Echo Lake Inn
Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98 reviews)
  • cleanliness
    Vermont countryside B&B close to Okemo Mountain Resort and Echo Lake.
The price is $291
$318 total
includes taxes & fees
Jan 20 - Jan 21
Echo Lake Inn
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.
View all properties

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
View properties in January
Currently viewing crowd sizes and weather for January.
Typical weather for Chester
January
High -2°C / low -11°C. Snow likely.
View properties in January
-2°
ac_unit
January, no crowd data, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
-11°
0°
ac_unit
February, no crowd data, average high temperature 0 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
-10°
4°
ac_unit
March, no crowd data, average high temperature 4 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
12°
weather_cloudy
April, no crowd data, average high temperature 12 degrees Celsius, average low temperature 1 degrees Celsius. Cloudy most days.
1°
19°
weather_sun
May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
23°
weather_sun
June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
27°
weather_sun
July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
26°
weather_sun
August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
22°
weather_sun
September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
15°
weather_partly_sunny
October, no crowd data, average high temperature 15 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
5°
7°
weather_partly_sunny
November, no crowd data, average high temperature 7 degrees Celsius, average low temperature -2 degrees Celsius. Partly sunny.
-2°
1°
ac_unit
December, no crowd data, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
Monthly weather averages (˚C)

Top neighborhoods in Chester

Chester Depot

The Chester Depot neighborhood has lots to see including Bonnie's Bundles Dolls and DaVallia Art & Accents.

Top landmarks in Chester

Bonnie's Bundles Dolls

Chester Depot is home to Bonnie's Bundles Dolls, so why not stop by during your stay in Chester. If you have fun at Bonnie's Bundles Dolls, you'll love DaVallia Art & Accents, located nearby.
See properties

DaVallia Art & Accents

Chester Depot is home to DaVallia Art & Accents, so why not stop by during your stay in Chester. If you have fun at DaVallia Art & Accents, you'll love Bonnie's Bundles Dolls, located nearby.
See properties

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.

See all hotels in Chester
aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Check out reviews of Chester hotels guests love

The Manchester View

The Manchester View

10/10 Excellent
"Excellent "
Rebecca 2-night trip
Posted 2 days ago
The Manchester View

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 35 vacation homes. You also might want to book one of 7 cottages or 10 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.