Hotels in Chester

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Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,000 reviews)
The price is $169
$193 total
includes taxes & fees
Apr 27 - Apr 28
Pointe at Castle Hill Resort
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 $209
$228 total
includes taxes & fees
Apr 27 - Apr 28
Stone Hearth Inn and Eatery
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, (1,006 reviews)
The price is $147
$161 total
includes taxes & fees
Apr 30 - May 1
Killington Mountain Lodge, Tapestry Collection by Hilton
Best Western Springfield Hotel
Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (853 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 3 - May 4
Best Western Springfield Hotel
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 5 - May 6
The Inn at Weathersfield
Fullerton Inn
Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (432 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
Apr 28 - Apr 29
Fullerton Inn
Align Inn Vermont
Align Inn Vermont
2.5 star property
Quechee
9.4 out of 10, Exceptional, (1,177 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
Apr 27 - Apr 28
Align Inn Vermont
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, (828 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 $139
$168 total
includes taxes & fees
May 4 - May 5
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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
Fireside Inn & Suites West Lebanon
Fireside Inn & Suites West Lebanon
2.5 star property
West Lebanon
8.2 out of 10, Very Good, (1,002 reviews)
The price is $140
$152 total
includes taxes & fees
May 10 - May 11
Fireside Inn & Suites West Lebanon
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 26 - May 27
Jackson Gore Village, A Vail Resorts Property
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (572 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 $309
$384 total
includes taxes & fees
Apr 27 - Apr 28
Woodstock Inn & Resort
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 $197
$215 total
includes taxes & fees
May 8 - May 9
Castle Hill Resort And Spa
The Mountain Inn at Killington
The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,000 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
Apr 27 - Apr 28
The Mountain Inn at Killington
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
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, (699 reviews)
The price is $107
$119 total
includes taxes & fees
May 25 - May 26
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.

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 April
Currently viewing crowd sizes and weather for April.
Typical weather for Chester
April
High 12°C / low 1°C. Cloudy most days.
View properties in April
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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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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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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 DaVallia Art & Accents and Bonnie's Bundles Dolls. Visitors speak highly of this relaxing city's coffeehouses and small-town setting.

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Check out reviews of Chester hotels guests love

Frequently asked questions

What accommodations do travelers recommend in Chester?
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.