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Nov 13 - Nov 15
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Nov 20 - Nov 22

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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

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (466 reviews)
"Stayed there 7yrs.ago and had another great experience this time, Cloe our waitress was excellent and made our dining alot of fun."
United States
Tim
The price is ā‚©173,266
ā‚©188,860 total
includes taxes & fees
Nov 12 - Nov 13
Fullerton Inn
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (130 reviews)
"Wonderful staff and restaurant"
United States
John
The price is ā‚©280,559
ā‚©305,809 total
includes taxes & fees
Nov 17 - Nov 18
Stone Hearth Inn and Eatery
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

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (894 reviews)
"Everything was excellent!"
United States
Dominick
The price is ā‚©204,307
ā‚©224,739 total
includes taxes & fees
Nov 17 - Nov 18
Best Western Springfield Hotel
A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

4. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,000 reviews)
"Amazing rooms, sweet staff, great amenities - gorgeous location!"
United States
Cristian
The price is ā‚©182,696
ā‚©208,274 total
includes taxes & fees
Nov 17 - Nov 18
Pointe at Castle Hill Resort
A bay window seating area with a round table, a potted plant, and a garland with pine cones and lights.

5. The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very good, (366 reviews)
"very historic place, beautiful and elegant"
United States
Zhenchun
The price is ā‚©251,169
ā‚©276,286 total
includes taxes & fees
Nov 12 - Nov 13
The Hartness House
A rustic dining area with wooden beams, tables, chairs, and a fireplace.

6. The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (83 reviews)
"Such a nice and kind family of owners. Breakfast was delicious, as well as dinner the previous night in their restaurant. Itā€™s a very rustic Inn, full of history and charm. We would love to return in the near future."
United States
Dorrie
The price is ā‚©277,911
ā‚©352,351 total
includes taxes & fees
Nov 29 - Nov 30
The Inn at Weathersfield
A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

7. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (450 reviews)
"We enjoyed our stay here."
United States
Anna
The price is ā‚©174,072
ā‚©188,874 total
includes taxes & fees
Dec 10 - Dec 11
The Common Man Inn & Restaurant
A two-story building with a patio area featuring outdoor seating and a stone fire pit.

8. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1,000 reviews)
"Great place, great location, super friendly staff and excellent amenities."
United States
Gerald
The price is ā‚©172,393
ā‚©189,632 total
includes taxes & fees
Nov 29 - Nov 30
Hampton Inn and Suites Manchester
A large stone building with a steep roof, surrounded by dense forest and hills.

9. Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (127 reviews)
"I promise, especially if youā€™re staying in the condo buildings you will love it"
United States
Brandon
The price is ā‚©240,558
ā‚©262,208 total
includes taxes & fees
Nov 17 - Nov 18
Castle Hill Resort And Spa
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

10. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (296 reviews)
"Staff was excellent and river views were amazing"
United States
John
The price is ā‚©218,255
ā‚©237,898 total
includes taxes & fees
Nov 27 - Nov 28
Harvest Barn Inn
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.

11. 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, (714 reviews)
"Beds and bedding were super comfy but the room itself was rather small and dated."
United States
Lynne
The price is ā‚©112,889
ā‚©129,258 total
includes taxes & fees
Nov 16 - Nov 17
The Upper Pass Lodge at Magic Mountain
A hotel with a covered entrance, a clear sky, and a tree in the foreground.

12. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,004 reviews)
"Easy check in, clean room and nice location"
United States
Alexander Cassidy
The price is ā‚©193,523
ā‚©212,876 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A large two-story house with a front porch and a well-maintained lawn.

13. The Landgrove

The Landgrove
3.5 star property
Londonderry
9.4 out of 10, Exceptional, (15 reviews)
"Had a great stay, room was set up with a very comfortable Home feel, not a sterile Hotel."
United States
Alan
The price is ā‚©224,749
ā‚©244,977 total
includes taxes & fees
Nov 18 - Nov 19
The Landgrove
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".

14. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
3.5 star property
Ludlow
9.6 out of 10, Exceptional, (235 reviews)
"Comfortable and clean property. Nicely appointed and well maintained. Great shower, comfy bed. Would stay again. And eat breakfast at the nearby Hatchery!"
United States
David
The price is ā‚©351,408
ā‚©386,558 total
includes taxes & fees
Nov 17 - Nov 18
Main and Mountain Bar & Motel
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

15. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (899 reviews)
"Very nice staff and enjoyed my stay."
United States
Charlene
The price is ā‚©154,267
ā‚©169,694 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn & Suites Brattleboro I-91
A hotel room with two beds, a wooden headboard, bedside lamps, and a window with curtains.

16. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (612 reviews)
"Room was clean and parking was right out front."
United States
Cindy
The price is ā‚©161,178
ā‚©174,878 total
includes taxes & fees
Nov 23 - Nov 24
Claremont Motor Lodge
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

17. 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, (973 reviews)
"Excellent place to stay!! The breakfas it good, bed comfortables and the view is nice."
United States
Adriana
The price is ā‚©248,060
ā‚©301,381 total
includes taxes & fees
Nov 18 - Nov 19
Jackson Gore Village, A Vail Resorts Property
A bedroom with a fireplace, two beds, a chair, and a nightstand.

18. The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (969 reviews)
"Great breakfast as well as a lovely property!"
United States
Pauline
The price is ā‚©152,400
ā‚©167,640 total
includes taxes & fees
Nov 16 - Nov 17
The Manchester View
A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

19. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (129 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is ā‚©200,129
ā‚©220,142 total
includes taxes & fees
Nov 15 - Nov 16
Blue Gentian Lodge at Magic Mountain
A two-story house with a red exterior and white trim. There are three large windows on the front and a chimney on the right side.

20. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (80 reviews)
"Quiet and peaceful."
United States
James
The price is ā‚©239,349
ā‚©260,893 total
includes taxes & fees
Dec 3 - Dec 4
COHO Inn & Motor Lodge
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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Where to stay in Chester

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

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.
See properties

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

On The River Inn

On The River Inn

8/10 Good
"My only quibble was that the bar and restaurant were not open during our 2 night stay and only on weekends. The hotel amenities were superb, the overall upkeep of this property and the decor with props etc was exceptional...."
Gail 2-night trip
Posted 5 hours ago
On The River Inn

More cheap stays in Chester

Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
The price is ā‚©116,313 per night from Nov 16 to Nov 17
ā‚©116,313
ā‚©142,705 total
Nov 16 - Nov 17
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.
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 pet-friendly accommodation in Chester?
Motel in the Meadow is a top pet-friendly option for your stay. 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 65Ā°F, while the coldest months are January and February with an average of 25Ā°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.