Hotels in Chester

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Tonight
May 10 - May 11
Tomorrow
May 11 - May 12
Next weekend
May 15 - May 17
In two weeks
May 22 - May 24

Where to stay in Chester?

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, (1,002 reviews)
The price is $169
$193 total
includes taxes & fees
May 11 - May 12
Pointe at Castle Hill Resort
Front of property
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (118 reviews)
Discover outdoor thrills with hiking, biking, and skiing nearby this charming B&B. Enjoy daily buffet breakfast and unwind after adventures. Bonnie's Bundles Dolls and DaVallia Art are just minutes away, with free WiFi and parking completing your Vermont getaway.
The price is $232
$253 total
includes taxes & fees
May 11 - May 12
Stone Hearth Inn and Eatery
Exterior
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1,005 reviews)
The price is $122
$134 total
includes taxes & fees
May 25 - May 26
Killington Mountain Lodge, Tapestry Collection by Hilton
Exterior
Best Western Springfield Hotel
Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (856 reviews)
Peaceful atmosphere awaits at this Springfield hotel, near State Fish and Wildlife Management Area and Baltimore Covered Bridge. Enjoy morning swims in the indoor pool, workout at the fitness center, and fuel up with free breakfast. Staff earns praise for helpfulness.
The price is $161
$177 total
includes taxes & fees
May 17 - May 18
Best Western Springfield Hotel
Interior
The Inn at Weathersfield
The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (79 reviews)
Discover a tranquil escape at this Perkinsville inn featuring a restaurant, bar, and beautiful garden terrace. With free breakfast, WiFi, and parking, you'll enjoy easy access to nearby North Springfield Lake and Stoughton Pond Recreation Area.
The price is $177
$230 total
includes taxes & fees
May 11 - May 12
The Inn at Weathersfield
Garden
Fullerton Inn
Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (433 reviews)
A cozy retreat in Chester offering complimentary breakfast, WiFi, and parking. The restaurant serves delicious meals, while the bar provides relaxing drinks after exploring nearby DaVallia Art & Accents or Bonnie's Bundles Dolls.
The price is $129
$141 total
includes taxes & fees
May 12 - May 13
Fullerton Inn
Lobby
Align Inn Vermont
Align Inn Vermont
2.5 star property
Quechee
9.4 out of 10, Exceptional, (1,188 reviews)
Peaceful sanctuary with an indoor pool and complimentary breakfast near Dartmouth College. Guests love the serene atmosphere, scenic surroundings, and 24/7 coffee service. Free WiFi and parking complete your Vermont retreat.
The price is $113
$124 total
includes taxes & fees
May 17 - May 18
Align Inn Vermont
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, (831 reviews)
This tranquil resort near Mount Ascutney features indoor and outdoor pools, tennis courts, and The Maple Kitchen serving American cuisine. Peaceful surroundings create the perfect setting for relaxation while maintaining easy access to local attractions.
The price is $149
$179 total
includes taxes & fees
May 11 - May 12
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Exterior
Motel in the Meadow
Motel in the Meadow
2.5 star property
Chester
8.4 out of 10, Very Good, (71 reviews)
Motel in the Meadow
Interior
Fireside Inn & Suites West Lebanon
Fireside Inn & Suites West Lebanon
2.5 star property
West Lebanon
8.2 out of 10, Very Good, (1,009 reviews)
The price is $146
$158 total
includes taxes & fees
May 31 - Jun 1
Fireside Inn & Suites West Lebanon
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, (852 reviews)
Experience the outdoor lifestyle at this ski resort hotel, just a 15-minute walk from Okemo Mountain Resort. Enjoy ski-in/ski-out access, indoor and outdoor pools, and a full-service spa. After adventures on the slopes, unwind at Coleman Brook Tavern or relax with a massage.
The price is $181
$220 total
includes taxes & fees
May 11 - May 12
Jackson Gore Village, A Vail Resorts Property
Lobby
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (576 reviews)
Unwind at this elegant Vermont resort with golf course, spa, and indoor pool near Middle Covered Bridge. Four restaurants serve American cuisine, while two bars offer evening relaxation. Travelers praise the attentive staff and central location.
The price is $319
$395 total
includes taxes & fees
May 25 - May 26
Woodstock Inn & Resort
Front of property
Castle Hill Resort And Spa
Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (118 reviews)
The price is $224
$244 total
includes taxes & fees
May 11 - May 12
Castle Hill Resort And Spa
Breakfast and dinner served
The Mountain Inn at Killington
The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,004 reviews)
Experience the ultimate ski vacation with slopeside convenience. This mountain retreat offers free breakfast and parking, plus an outdoor pool to relax after hitting the slopes. Near both Killington and Pico Mountain resorts, you'll appreciate the helpful staff and cozy bar/lounge.
The price is $149
$172 total
includes taxes & fees
May 11 - May 12
The Mountain Inn at Killington
Front of property - evening/night
Golden Stage Inn B&B
Golden Stage Inn B&B
3.5 star property
Cavendish
10.0 out of 10, Exceptional, (44 reviews)
Golden Stage Inn B&B
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, (700 reviews)
The price is $121
$134 total
includes taxes & fees
Jun 8 - Jun 9
The Upper Pass Lodge at Magic Mountain
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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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 May
Currently viewing crowd sizes and weather for May.
Typical weather for Chester
May
High 19°C / low 7°C. Sunny most days.
View properties in May
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May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 15 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
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November, no crowd data, average high temperature 7 degrees Celsius, average low temperature -2 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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January, no crowd data, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 0 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 4 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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April, no crowd data, average high temperature 12 degrees Celsius, average low temperature 1 degrees Celsius. Cloudy most days.
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Monthly weather averages (˚C)

Top neighborhoods in Chester

panoramic view of colorful foliage in White mountain national forest in New Hampshire along Kancamagus highway

Chester Depot

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

Top landmarks in Chester

DaVallia Art & Accents

5.0/5 (2 reviews)
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.
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Learn more about Chester

Notable for its skiing, Chester features attractions such as DaVallia Art & Accents and Bonnie's Bundles Dolls. 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 Shire Woodstock

The Shire Woodstock

2/10 Terrible
"The hotel is under renovations and it was not mentioned. The lock on our door broke and we were locked in. They sent two workers thru a window to get us out. Then when we took a shower there was no hot water. I would like a refund this was not acceptable ever."
Michael 1-night trip
Posted 9 hours ago
The Shire Woodstock

Frequently asked questions

What accommodations do travelers recommend in Chester?
Guests like Fullerton Inn and Pointe at Castle Hill Resort.
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 32 vacation homes. You also might want to book one of 7 cottages or 11 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.