Top 10 Hotels in Chester, VT from ￥14,083 - Competitive Prices

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Our top choices for Chester hotels

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

1. Fullerton Inn

Chester Depot

Tim

￥22,284 total

includes taxes & fees

Nov 10 - Nov 11

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

2. Stone Hearth Inn and Eatery

Chester

John

￥32,836 total

includes taxes & fees

Nov 16 - Nov 17

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

3. Best Western Springfield Hotel

Springfield

Dominick

￥26,516 total

includes taxes & fees

Nov 15 - Nov 16

A bay window seating area with a round table, a potted plant, and a garland with pine cones and lights.

4. The Hartness House

Springfield

Zhenchun

￥32,812 total

includes taxes & fees

Nov 10 - Nov 11

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

5. Pointe at Castle Hill Resort

Cavendish

Cristian

￥26,326 total

includes taxes & fees

Nov 15 - Nov 16

A rustic dining area with wooden beams, tables, chairs, and a fireplace.

6. The Inn at Weathersfield

Perkinsville

Dorrie

￥40,503 total

includes taxes & fees

Dec 9 - Dec 10

A two-story building with a patio area featuring outdoor seating and a stone fire pit.

7. Hampton Inn and Suites Manchester

Manchester Center

Rosemary

￥22,375 total

includes taxes & fees

Nov 15 - Nov 16

A large stone building with a steep roof, surrounded by dense forest and hills.

8. Castle Hill Resort And Spa

Cavendish

Brandon

￥26,917 total

includes taxes & fees

Nov 15 - Nov 16

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.

9. The Upper Pass Lodge at Magic Mountain

Londonderry

Lynne

￥15,242 total

includes taxes & fees

Nov 16 - Nov 17

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

10. The Common Man Inn & Restaurant

Claremont

Anna

￥22,285 total

includes taxes & fees

Nov 12 - Nov 13

A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

11. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

￥19,575 total

includes taxes & fees

Nov 15 - Nov 16

A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

12. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

￥25,977 total

includes taxes & fees

Nov 9 - Nov 10

A hotel room with two beds, a wooden headboard, bedside lamps, and a window with curtains.

13. Claremont Motor Lodge

Claremont

Katie

￥19,397 total

includes taxes & fees

Nov 10 - Nov 11

A hotel with a covered entrance, a clear sky, and a tree in the foreground.

14. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

￥24,231 total

includes taxes & fees

Dec 6 - Dec 7

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

15. Harvest Barn Inn

Bellows Falls

John

￥27,229 total

includes taxes & fees

Nov 28 - Nov 29

A large two-story house with a front porch and a well-maintained lawn.

16. The Landgrove

Londonderry

Alan

￥28,904 total

includes taxes & fees

Nov 16 - Nov 17

A stone fire pit with chairs around it, set in a grassy area with trees and a large building in the background.

17. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Richard

￥24,876 total

includes taxes & fees

Nov 9 - Nov 10

A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

18. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Adriana

￥35,561 total

includes taxes & fees

Nov 18 - Nov 19

A hotel room with two beds, a desk, and a TV.

19. The Putney Inn

Putney

Kristen

￥14,083 total

includes taxes & fees

Dec 8 - Dec 9

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

20. Main and Mountain Bar & Motel

Ludlow

David

￥45,610 total

includes taxes & fees

Nov 16 - Nov 17

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Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most.

Chester Depot

A forest with autumn foliage in various colors.

Chester Depot

If you're spending some time in Chester Depot, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.

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Stay near popular Chester attractions

Bonnie's Bundles Dolls

7.6/10 (4 reviews)

This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.

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Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester

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

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Lovely location. Happy, attentive staff, quiet, lots of parking. Definitely go back again. Only problem was the hotel and room was very warm. The staff gladly provided a fan."

Woodstock Inn & Resort

10/10 Excellent

"Fantastic stay at Woodstock Inn this week! The room and property were spotless, and the staff was incredibly kind and welcoming. The spa was beautiful, the food at Red Rooster was excellent, and the athletic center, pool, and hot tub were all great. The entire property has a quiet, peaceful atmosphere that makes it easy to relax and unwind. Would absolutely recommend!"

Hideaway Inn Mt. Snow

10/10 Excellent

"The room was small and simple, but nicely decorated, including a record player with a vinyl album (cover, at least; didn't check for actual vinyl). The room was warm and the place was quiet when I stayed, which was off-season. I've been pulling into the parking lot of this place for five years now (MOOver), so staying there was interesting for me. I stayed there during a HAZMAT spill that closed Woodford Mtn for a couple days. Of special note, this is the ONLY hotel I've ever stayed at that had a sleep/sound machine in the room. I ALWAYS take one with me when traveling, but this was a last minute decision, so I would've had to pull up something on my phone, but there was a nice sound machine on the nightstand and I used it. Those are so helpful when staying in hotels/inns."

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"

More cheap stays in Chester

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

￥14,548

￥15,785 total

Nov 10 - Nov 11

includes taxes & fees

Frequently asked questions

Where is the best place to stay in Chester?

Based on our traveler data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. Stone Hearth Inn and Eatery is another good choice for your stay. See all available top hotels, or vacation rentals in Chester.

What's the top vacation rental that Chester has to offer?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: Visitors like this Chester vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

For additional details about rescheduling or cancelling your trip to Chester, head over to our customer service page.

What's the best hotel for a family vacation to Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a guesthouse with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families. Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are also fun for kids of all ages. Find more child-friendly accommodations in Chester.

What's the best accommodation for a romantic vacation in Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favorite guesthouse for couples, and features free WiFi and a garden. See all romantic hotels in Chester.

What's the best pet-friendly accommodation in Chester?

Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains is a top pet-friendly option for your stay. Motel in the Meadow is another good choice for you and your pet. See more pet-friendly hotel accommodations in Chester.

What are some accommodations with pools in Chester?

Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. Aspen At Manchester and The Manchester View are two additional hotels with an onsite pool. View all hotels with pools in Chester.

What's the best accommodation near Hartness State Airport (VSF)?

The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.

What is staying in Chester like?

Visitors to Chester are sure to enjoy the ski areas, coffeehouses, and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 67 hotels and other accommodations to choose from. Find out more about Chester.

What should I see while I'm in Chester?

A couple of favorite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. You'll also find Vermont Country Store and Lowell Lake State Park in the area. Check out what more to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.

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Find hotels in Chester, VT from ￥14,083

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Our top choices for Chester hotels

1. Fullerton Inn

2. Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

4. The Hartness House

5. Pointe at Castle Hill Resort

6. The Inn at Weathersfield

7. Hampton Inn and Suites Manchester

8. Castle Hill Resort And Spa

9. The Upper Pass Lodge at Magic Mountain

10. The Common Man Inn & Restaurant

11. Comfort Inn & Suites Brattleboro I-91

12. Blue Gentian Lodge at Magic Mountain

13. Claremont Motor Lodge

14. Holiday Inn Express Hotel & Suites Brattleboro by IHG

15. Harvest Barn Inn

16. The Landgrove

17. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

18. Jackson Gore Village, A Vail Resorts Property

19. The Putney Inn

20. Main and Mountain Bar & Motel

Where to stay in Chester

Chester Depot

Stay near popular Chester attractions

Bonnie's Bundles Dolls

Learn more about Chester

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Frequently asked questions

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