Hotels in Chester

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Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 conference room with a long wooden table, multiple chairs, and a large window providing natural light.
A bedroom with a bed, a fireplace, a window, a dresser, and a clock on the wall.

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
$282
$307 total
includes taxes & fees
Oct 22 - Oct 23
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 hotel with a pool, multiple balconies, and a snow-covered ground.
A stone fireplace with a modern seating area, including a sofa and chairs, a coffee table, and a decorative bowl.

3. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
Killington
$144
$158 total
includes taxes & fees
Nov 2 - Nov 3
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 sofa, a coffee table, a desk, and a TV.
An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.
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 living room with a sofa, ottoman, armchair, and a television on a stand.
An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.
A bedroom with a large bed, a bedside table, a lamp, and a view of the outdoors through a sliding door.

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 bedroom with a bed, a bedside table, a lamp, a mirror, a dresser, a window, and a ceiling fan.

6. Fullerton Inn

Fullerton Inn
Chester Depot
$149
$162 total
includes taxes & fees
Nov 1 - Nov 2
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 patio with two wicker chairs and a table, surrounded by greenery and a white structure.
A hotel bathroom with a granite countertop, a sink, a mirror, and a wicker basket with towels.

7. Align Inn Vermont

Align Inn Vermont
Quechee
$124
$137 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 group of people gathered around a fire pit in a snowy outdoor setting with a large building in the background.
A living room with a fireplace, a sofa, a coffee table, and a television.
A spacious living area with a staircase, patterned sofas, a coffee table, and a decorative wall piece.

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 bunk beds, a desk with a lamp, and a chair.
A room with a bed, a chair, a lamp, and a wall with wooden paneling.
A room with two beds, a wooden nightstand, and a television.

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.
A cozy lobby with a stone fireplace, leather sofas, and a coffee table.
A spacious indoor dining area with multiple wooden tables and chairs, surrounded by various plants and trees.
An indoor swimming pool with a curved design, surrounded by seating areas and plants.

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 balcony with a stone wall and wooden railing overlooking a grassy area with a building in the background.
A golf course with rolling hills, trees, and a distant mountain range.
A hot tub with a tiled interior and a window in the background.

11. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
$180
$219 total
includes taxes & fees
Oct 26 - Oct 27
Jackson Gore Village, A Vail Resorts Property
A room with a checkered floor, a bench, and a fireplace.
A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.
A rustic dining area with wooden beams, a chandelier, and a kitchen in the background.
A spacious living room with a grand chandelier, large windows, and a comfortable seating area.

12. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
$439
$527 total
includes taxes & fees
Nov 2 - Nov 3
Woodstock Inn & Resort
A large stone building with a steep roof, surrounded by dense forest and hills.
A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.
A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.
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 swimming pool surrounded by snow, with a building in the background.

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.
A park with a paved walkway, a small pond, and various trees.
Two people in a swimming pool with inflatable rings.
A snowy outdoor area with a railing and four wine glasses filled with red wine.

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
$106
$122 total
includes taxes & fees
Nov 8 - Nov 9
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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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

Fullerton Inn

Fullerton Inn

10/10 Excellent
"Room was small but clean. Staff very helpful and welcoming. Parking available right outside the hotel. There was a fridge close to reception for guest use. Lovely location in a typical New England town with lots of interesting shops. Bar offered a good selection of draft beers. Continental breakfast had very little left at 9.00am - probably our own fault for leaving it so late. Would definitely return."
Anita 1-night trip
Posted less than an hour ago
Fullerton Inn
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good
"Nice hotel. Dated, but nice. Internet speed and connectivity is terrible. Good launching point for the Stowe area attractions to allow access off of back routes to avoid traffic. No breakfast."
Steven 1-night trip
Posted 5 hours ago
The Black Bear Lodge at Stratton Mountain Resort
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

8/10 Good
"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 nights because of the difficulty of the stairs… It was however nice if no handicaps"
Dorothy 2-night trip
Posted 15 hours ago
Stone Hearth Inn and Eatery
The Manchester View

The Manchester View

8/10 Good
"The lodge was in a picturesque location with lots of amenities. The rooms were clean apart from bugs in the window seals and in the main community areas. Lots of spider webs in lamp shades and around window areas. Just seemed to be overlooked for a long time. Unfortunately, we did not have a window screen on our room window in order to cool the room off due to the AC unit not functioning properly. We did find a fan which helped some. The breakfast was delicious and it was overall a comfortable place to stay and relax. I would definitely return for the views and location. Hopefully with the new staff in place, the lodge will improve in other areas needing attention."
Amanda 1-night trip
Posted 20 hours ago
The Manchester View
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Lovely feel to the hotel with friendly staff. Room was comfortable and location is excellent. Love Woodstock as a destination. I am never the biggest fan of breakfast, but really enjoyed it for once"
patrick 3-night trip
Posted 20 hours ago
Woodstock Inn & Resort
Latchis Hotel

Latchis Hotel

8/10 Good
"We enjoyed our stay at the historic Latchis Hotel. You really get the feeling of stepping back in time. The staff were very helpful and provided recommendations on places to eat besides just checking us in. The room was fine and the working record player with records was a nice touch. Parking is about a half block away behind the hotel. Make sure you see the historic Latchis Theater’s main room. It is really amazing and will definitely take you back in time."
Jaren 1-night trip
Posted 1 day ago
Latchis Hotel
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

8/10 Good
"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received our check-in information, we were given a room on the 2nd floor. If we only had to carry backpacks, it might have been fine. However, we had large cases, so it was difficult to drag them up the stairs. Also, if you are an above average size person, know that these rooms are small spaces. The bathroom is barely big enough to turn around in and the shower is tiny."
KERRY 1-night trip
Posted 2 days ago
Hideaway Inn Mt. Snow
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"Allen in the restaurant is great."
Bettina 1-night trip
Posted 2 days ago
Grand Summit Resort, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

8/10 Good
"Everything about this property was exceptional, EXCEPT the bed. We had an amazing time, enjoyed the lift to view fall colors & mountain coaster. But we had a miserable experience sleeping. The beds are like rock. I know it's the granite state, but get some toppers!"
Pamela 4-night trip
Posted 2 days ago
Jackson Gore Village, A Vail Resorts Property

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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