Find hotels in Chester, VT from ฿3,504

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4 Nov - 5 Nov
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5 Nov - 6 Nov
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7 Nov - 9 Nov
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Top 10 Chester hotels and places to stay

Garden
Fullerton Inn
Fullerton Inn
2.5 star property
8.2 out of 10, Very good, (399)
"What an absolutely charming Inn. The room was very clean and comfortable, the food in the restaurant was outstanding, and the staff was wonderful. Overall, it was a great experience and I will definitely be back!"
United States
AJ
The price is ฿4,171
฿4,546 total
includes taxes & fees
11 Nov - 12 Nov
Fullerton Inn
Front of property
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (105)
"Room was super quiet and clean. "
United States
Ernest
The price is ฿6,753
฿7,361 total
includes taxes & fees
19 Nov - 20 Nov
Stone Hearth Inn and Eatery
Lobby
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 star property
9.2 out of 10, Wonderful, (546)
"This was our ideal hotel! Charmingly decorated, functional, and a walking distance to the town. We appreciated the complimentary champagne on our arrival, it was a wonderful place to spend our honeymoon."
United States
Evan and Nicole
The price is ฿10,368
฿12,834 total
includes taxes & fees
30 Nov - 1 Dec
Woodstock Inn & Resort
Property grounds
The Shire Woodstock
The Shire Woodstock
3.0 star property
8.8 out of 10, Excellent, (875)
"Everything was awesome! Great view and very clean. Just what we were looking for. Very easy check in and out"
United States
Ahmed
The Shire Woodstock
Meeting facility
Aspen At Manchester
Aspen At Manchester
2.5 star property
8.8 out of 10, Excellent, (598)
"Very nice hotel. Clean and looked recently remodeled. It was very quiet, allowing me to relax. Will stay here again when in the area."
United States
Grant
The price is ฿3,481
฿4,186 total
includes taxes & fees
30 Nov - 1 Dec
Aspen At Manchester
Deluxe Suite | 2 bedrooms, individually decorated, desk, blackout curtains
Sleep Woodstock Motel
Sleep Woodstock Motel
2.0 star property
9.6 out of 10, Exceptional, (540)
"Great motel with complete amenities.. beautiful surrounding especially in this fall"
United States
Giana
The price is ฿3,346
฿5,104 total
includes taxes & fees
11 Nov - 12 Nov
Sleep Woodstock Motel
Exterior
The Palmer House Resort, an Ascend Collection Hotel
The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
8.4 out of 10, Very good, (853)
"The area around the Palmer House is so beautiful. Mountains everywhere!! "
United States
Mark
The price is ฿3,270
฿4,130 total
includes taxes & fees
16 Nov - 17 Nov
The Palmer House Resort, an Ascend Collection Hotel
Front of property – evening/night
Hampton Inn and Suites Manchester
Hampton Inn and Suites Manchester
2.5 star property
9.6 out of 10, Exceptional, (1005)
"Very dog friendly."
United States
Gene
The price is ฿4,215
฿4,637 total
includes taxes & fees
16 Nov - 17 Nov
Hampton Inn and Suites Manchester
Indoor spa tub
The Black Bear Lodge at Stratton Mountain Resort
The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
7.6 out of 10, Good, (931)
"Great place for the price "
United States
Karen
The price is ฿4,817
฿5,829 total
includes taxes & fees
10 Nov - 11 Nov
The Black Bear Lodge at Stratton Mountain Resort
Exterior detail
The Covered Bridge Inn
The Covered Bridge Inn
2.5 star property
7.6 out of 10, Good, (1004)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is ฿3,270
฿3,597 total
includes taxes & fees
6 Nov - 7 Nov
The Covered Bridge Inn
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3.0 star property
8.4 out of 10, Very good, (1008)
"Hotel was great."
United States
Heidi
The price is ฿4,817
฿5,227 total
includes taxes & fees
5 Nov - 6 Nov
Best Western Plus Keene Hotel
In-room safe, desk, blackout curtains, iron/ironing board
Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NH
2.0 star property
7.0 out of 10, Good, (1005)
"Great stay"
United States
Michael
The price is ฿3,270
฿3,548 total
includes taxes & fees
9 Nov - 10 Nov
Days Inn by Wyndham Keene NH
Exterior
Kimpton Taconic Hotel by IHG
Kimpton Taconic Hotel by IHG
4.0 star property
9.4 out of 10, Exceptional, (812)
"Very nice, beautiful inn"
United States
Susan
The price is ฿5,140
฿6,899 total
includes taxes & fees
1 Dec - 2 Dec
Kimpton Taconic Hotel by IHG
Indoor pool
Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 star property
8.8 out of 10, Excellent, (910)
"Love this place and we will be back again, the bed is awesome and I like all the pillows and the comfort as u feel when u walk in "
United States
Jennie
The price is ฿5,140
฿5,860 total
includes taxes & fees
6 Nov - 7 Nov
Pointe at Castle Hill Resort
Exterior
The Equinox Golf Resort & Spa
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (563)
"Beautiful hotel! "
United States
sarah
The price is ฿3,557
฿5,634 total
includes taxes & fees
17 Nov - 18 Nov
The Equinox Golf Resort & Spa
Property grounds
The Manchester View
The Manchester View
2.5 star property
9.4 out of 10, Exceptional, (771)
"The setting is quiet peaceful and the accommodation is like home "
United States
diane
The price is ฿3,185
฿3,504 total
includes taxes & fees
5 Nov - 6 Nov
The Manchester View
Sun deck
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel
2.5 star property
9.6 out of 10, Exceptional, (621)
"Loved my stay"
United States
Christine
The price is ฿4,919
฿5,337 total
includes taxes & fees
30 Nov - 1 Dec
Riverside Hotel, an Ascend Collection Hotel
Free daily on-the-go breakfast
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
8.8 out of 10, Excellent, (1007)
"The nicest Holiday Inn Express I have ever stayed at. Lovely place and super clean."
United States
WOODROW
The price is ฿4,914
฿5,406 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Outdoor dining
Vantage Point Villas at Stratton Mountain Resort
Vantage Point Villas at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (70)
"Great place to stay! We went on a last minute Father’s Day weekend trip and had the best time! Great location close to the shops and restaurants. "
United States
Roberta
The price is ฿8,050
฿10,006 total
includes taxes & fees
10 Nov - 11 Nov
Vantage Point Villas at Stratton Mountain Resort
Property entrance
Jackson Gore Village
Jackson Gore Village
3.0 star property
8.6 out of 10, Excellent, (828)
"The hotel was peaceful and clean, perfect for the weekend getaway."
United States
Terrence
The price is ฿6,013
฿7,306 total
includes taxes & fees
6 Nov - 7 Nov
Jackson Gore Village
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 for the activities you enjoy most.

Chester Depot

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

Stay near popular Chester attractions

DaVallia Art & Accents

This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.
See properties

Bonnie's Bundles Dolls

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

Top Chester Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Everything was awesome! Great view and very clean. Just what we were looking for. Very easy check in and out"
Ahmed 3-night trip
Posted 2 days ago
The Shire Woodstock

More cheap stays in Chester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT
The price is ฿3,270 per night from 6 Nov to 7 Nov
฿3,270
฿3,597 total
6 Nov - 7 Nov
includes taxes & fees
7.6/10 Good! (1,001 reviews)

Frequently asked questions

Where is the best place to stay in Chester?
Stone Hearth Inn and Eatery is ranked highly by Expedia customers. This B&B offers free breakfast and free parking. Another top choice for your trip based on reviews is Fullerton Inn. 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 if cancelled prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What's the best dog-friendly accommodation option in Chester?
Motel in the Meadow is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Chester.
What are some accommodation options with pools in Chester?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Pointe at Castle Hill Resort and The Equinox Golf Resort & Spa are two additional hotels that feature an on-site pool. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors to Chester will definitely enjoy the skiing, cafes and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 67 hotels and other accommodation options to choose from. Find out more about Chester.
What should I do while I'm visiting Chester?
A couple of favourite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. You'll also find Grafton Historical Society and Vermont Country Store in the area. Take a look at what more there is 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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.

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