Hotels in Chester

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Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Where to stay in Chester?

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.
A spacious lobby with a fireplace, leather seating, and a chandelier.
An indoor swimming pool with four chairs and a hot tub.
A sign for Castle Hill Spa surrounded by lush greenery and a well-maintained lawn.

1. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
$152
$174 total
includes taxes & fees
Oct 28 - Oct 29
Pointe at Castle Hill Resort
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.
A white house with a porch, wooden chairs, and an American flag.
A living room with two sofas, a fireplace, and a wooden floor.
A conference room with a long wooden table, multiple chairs, and a large window providing natural light.

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
$209
$228 total
includes taxes & fees
Nov 17 - Nov 18
Stone Hearth Inn and Eatery
A large, multi-story hotel with a prominent entrance and a staircase leading to the upper levels.
A spacious loft-style living area with high ceilings, exposed wooden beams, and a mezzanine level.
A stone fireplace with a modern seating area, including a sofa and chairs, a coffee table, and a decorative bowl.
A patio area with a fire pit, outdoor seating, and a swimming pool.

3. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
Killington
$137
$151 total
includes taxes & fees
Nov 1 - Nov 2
Killington Mountain Lodge, Tapestry Collection by Hilton
A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.
A hotel room with a bed, a sitting area, a bathroom with a bathtub, and a large mirror.
A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.
A spacious, well-lit kitchen area with modern appliances, a central island with bar stools, and a chandelier.

4. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
$152
$167 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Springfield Hotel
A rustic dining area with wooden beams, tables, chairs, and a fireplace.
A bedroom with a large bed, a bedside table, a lamp, and a view of the outdoors through a sliding door.
An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.
A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.

5. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
$227
$284 total
includes taxes & fees
Nov 5 - Nov 6
The Inn at Weathersfield
A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.
A two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.
A cozy living room with a stone fireplace, a leather sofa set, a wooden coffee table, and a patterned rug.
A variety of dishes including a steak, muffins, and a dessert with fruit.

6. Fullerton Inn

Fullerton Inn
Chester Depot
$129
$141 total
includes taxes & fees
Nov 10 - Nov 11
Fullerton Inn
A spacious living room with a stone fireplace, leather sofas, a coffee table, and large arched windows offering views of the outdoors.
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.
A hotel bathroom with a granite countertop, a sink, a mirror, and a wicker basket with towels.
A patio with two wicker chairs and a table, surrounded by greenery and a white structure.

7. Align Inn Vermont

Align Inn Vermont
Quechee
$123
$135 total
includes taxes & fees
Nov 1 - Nov 2
Align Inn Vermont
A multi-story hotel with a central courtyard and a reflective water feature.
A bar area with stools, a counter, and a large window offering a view of a snowy landscape.
A living room with a fireplace, a sofa, a coffee table, and a television.
A group of people gathered around a fire pit in a snowy outdoor setting with a large building in the background.

8. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
$139
$168 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
A motel sign with a gift shop and a Visa sign in the background.
A room with two beds, a wooden nightstand, and a television.
A room with bunk beds, a desk with a lamp, and a chair.
A compact room with a kitchenette, two beds with floral bedding, a chair, and a lamp.

9. Motel in the Meadow

Motel in the Meadow
Chester
Motel in the Meadow
An indoor dining area with multiple wooden tables and chairs, surrounded by lush greenery and a stone water feature.
An indoor swimming pool with a curved design, surrounded by seating areas and plants.
A spacious indoor dining area with multiple wooden tables and chairs, surrounded by various plants and trees.
A cozy lobby with a stone fireplace, leather sofas, and a coffee table.

10. Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon
West Lebanon
$140
$152 total
includes taxes & fees
Nov 1 - Nov 2
Fireside Inn & Suites West Lebanon
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.
A hot tub with a tiled interior and a window in the background.
A hotel with a swimming pool area, including two hot tubs and lounge chairs.
A golf course with rolling hills, trees, and a distant mountain range.

11. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
$186
$227 total
includes taxes & fees
Nov 18 - Nov 19
Jackson Gore Village, A Vail Resorts Property
A room with a checkered floor, a bench, and a fireplace.
A spacious living room with a grand chandelier, large windows, and a comfortable seating area.
A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.
A spacious room with large windows, a fireplace, and comfortable seating areas.

12. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
$369
$450 total
includes taxes & fees
Nov 16 - Nov 17
Woodstock Inn & Resort
A large stone building with a steep roof, surrounded by dense forest and hills.
A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.
A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.
A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.

13. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
$269
$293 total
includes taxes & fees
Oct 19 - Oct 20
Castle Hill Resort And Spa
A building with a modern design, featuring large windows and a covered outdoor seating area.
A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs, a piano, and a view of the outside.
A hotel room with two beds, a wooden headboard, a desk, and a window with a view of greenery.
A lobby with a stone wall, wooden staircase, and a reception desk.

14. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
$149
$172 total
includes taxes & fees
Oct 19 - Oct 20
The Mountain Inn at Killington
A two-story house with a snow-covered yard and a well-lit front porch.
Two people in a swimming pool with inflatable rings.
A room with two patterned chairs, a table with a lamp, a mirror, and a framed picture on the wall.
A park with a paved walkway, a small pond, and various trees.

15. Golden Stage Inn B&B

Golden Stage Inn B&B
Cavendish
Golden Stage Inn B&B
A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.
A hotel room with a large bathtub, a bed with a colorful quilt, two bedside lamps, and a framed picture on the wall.
A Christmas tree decorated with lights, ornaments, and a bow.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".

16. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
$99
$113 total
includes taxes & fees
Nov 18 - Nov 19
The Upper Pass Lodge at Magic Mountain
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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 October
Typical weather for Chester
October
High 15°C / low 5°C. Partly sunny.
View properties in October
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27°
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Monthly weather averages (˚C)

Top neighborhoods in Chester

A forest with autumn foliage in various colors.

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

7.6/10 (4 reviews)
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.
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DaVallia Art & Accents

10.0/10 (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
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Check out reviews of Chester hotels guests love

Colonial Motel

Colonial Motel

10/10 Excellent
"Room wasn’t the cleanest but can tell they’re in the process of renovating. Pet friendly which was amazing and a reasonable price"
Tracy 2-night trip
Posted 1 hour ago
Colonial Motel
Latchis Hotel

Latchis Hotel

10/10 Excellent
"Had a wonderful stay. Great room with a beautiful view of the mountains. And we absolutely loved that every room had a record player with historic records to play and enjoy - what a cool feature!"
Brent 1-night trip
Posted 2 hours ago
Latchis Hotel
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Everything was good; but continental breakfast was poor; there was no eggs"
MUSTAFA 2-night trip
Posted 3 hours ago
The Black Bear Lodge at Stratton Mountain Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Beautiful resort with amazing beds! Very comfortable."
Sara 4-night trip
Posted 4 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"I would suggest get there before it gets dark. The roads are very dark. No fault to the hotel at all just dark country roads."
Rebecca 1-night trip
Posted 21 hours ago
Jackson Gore Village, A Vail Resorts Property
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"Hot tub wasn’t up and running, was looking forward to utilizing that amenity. Food was basically just freezer food, even the salads were below average. Service was great though."
John 2-night trip
Posted 1 day ago
Grand Summit Resort, A Vail Resorts Property
Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"It was very modern looking well renovated properties a hole, and we were very well taken care of throughout our one night there."
Nathan 1-night trip
Posted 1 day ago
Aspen At Manchester
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Staff very friendly. Location was a plus. Room clean with comfortable bed."
Kevin 1-night trip
Posted 2 days ago
Hampton Inn and Suites Manchester
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

10/10 Excellent
"This was a nice place. The staff was great as there were prompt responses to my inquiries. The property is a little dated but clean. We were not there long enough to enjoy the amenities. I would stay again."
Kelly 1-night trip
Posted 3 days ago
Hideaway Inn Mt. Snow

Frequently asked questions

What accommodations do travelers recommend in Chester?
Guests like Fullerton Inn, Stone Hearth Inn and Eatery 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 31 vacation homes. You also might want to book one of 6 cottages or 13 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.

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