Find hotels in Chester, VT from ￥14,345

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 10 - Nov 11
Tomorrow
Nov 11 - Nov 12
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Filter by

Guest rating
Guest rating
Star rating

Compare 3,014 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Garden
Fullerton Inn

Fullerton Inn

2.5 star property
Chester Depot
8.2 out of 10, Very Good, (401)
"A unique inn in a charming town. Breakfast falls short, but staff is friendly and helpful "
United States
Dominique
The price is ￥19,791
￥21,572 total
includes taxes & fees
Nov 11 - Nov 12
Fullerton Inn
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Room was super quiet and clean. "
United States
Ernest
The price is ￥28,522
￥31,089 total
includes taxes & fees
Nov 24 - Nov 25
Stone Hearth Inn and Eatery
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (547)
"I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn"
United States
Kevin
The price is ￥50,475
￥62,273 total
includes taxes & fees
Nov 30 - Dec 1
Woodstock Inn & Resort
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (880)
"Upon entering the hotel, the lobby is gorgeous with 2 fireplaces. Staff was super friendly and the free breakfast was a bonus. The room was spotless and has a fireplace in the room. My wife and I loved this place and will definitely go back. "
United States
Vincent
The price is ￥18,042
￥21,037 total
includes taxes & fees
Nov 18 - Nov 19
The Shire Woodstock
Meeting facility
Aspen At Manchester

Aspen At Manchester

2.5 star property
Manchester Center
8.8 out of 10, Excellent, (599)
"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 ￥15,155
￥18,356 total
includes taxes & fees
Dec 11 - Dec 12
Aspen At Manchester
Deluxe Suite | 2 bedrooms, individually decorated, desk, blackout drapes
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (540)
"Great motel with complete amenities.. beautiful surrounding especially in this fall"
United States
Giana
The price is ￥15,879
￥24,219 total
includes taxes & fees
Nov 11 - Nov 12
Sleep Woodstock Motel
Exterior
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3.0 star property
Manchester Center
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 ￥15,518
￥19,600 total
includes taxes & fees
Dec 1 - Dec 2
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
Manchester Center
9.6 out of 10, Exceptional, (1002)
"The hotel was clean, the staff was friendly, and was a great location. The new Brewery on the property was great as well!"
United States
Jake
The price is ￥19,515
￥21,466 total
includes taxes & fees
Nov 30 - Dec 1
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
Stratton
7.6 out of 10, Good, (932)
"Great place for the price "
United States
Karen
The price is ￥19,661
￥23,790 total
includes taxes & fees
Nov 18 - Nov 19
The Black Bear Lodge at Stratton Mountain Resort
Exterior detail
The Covered Bridge Inn

The Covered Bridge Inn

2.5 star property
Brattleboro
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 ￥13,041
￥14,345 total
includes taxes & fees
Nov 11 - Nov 12
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
Keene
8.4 out of 10, Very Good, (1004)
"Hotel was great."
United States
Heidi
The price is ￥22,860
￥24,804 total
includes taxes & fees
Nov 11 - Nov 12
Best Western Plus Keene Hotel
Exterior
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4.0 star property
Manchester
9.4 out of 10, Exceptional, (812)
"Very nice, beautiful inn"
United States
Susan
The price is ￥24,394
￥32,740 total
includes taxes & fees
Dec 1 - Dec 2
Kimpton Taconic Hotel by IHG
Exterior
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (566)
"Nice old Inn!"
United States
Daniel
The price is ￥16,247
￥26,014 total
includes taxes & fees
Nov 17 - Nov 18
The Equinox Golf Resort & Spa
Indoor pool
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 star property
Cavendish
8.8 out of 10, Excellent, (916)
"Clean room, great staff, wonderful suggestions for area restaurants and attractions."
United States
Margie
The price is ￥19,759
￥22,526 total
includes taxes & fees
Nov 11 - Nov 12
Pointe at Castle Hill Resort
In-room safe, desk, blackout drapes, iron/ironing board
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2.0 star property
Keene
7.0 out of 10, Good, (1000)
"Very professional people good service good staff "
United States
George
The price is ￥15,518
￥16,837 total
includes taxes & fees
Nov 13 - Nov 14
Days Inn by Wyndham Keene NH
Property grounds
The Manchester View

The Manchester View

2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (771)
"The setting is quiet peaceful and the accommodation is like home "
United States
diane
The Manchester View
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
Brattleboro
8.8 out of 10, Excellent, (1003)
"Friendly, efficient staff and a very clean and nice room"
United States
Margaret
The price is ￥21,786
￥23,964 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Sundeck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (622)
"Loved my stay"
United States
Christine
The price is ￥23,343
￥25,327 total
includes taxes & fees
Dec 9 - Dec 10
Riverside Hotel, an Ascend Collection Hotel
Outdoor dining
Vantage Point Villas at Stratton Mountain Resort

Vantage Point Villas at Stratton Mountain Resort

3.0 star property
Stratton
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 ￥32,855
￥40,840 total
includes taxes & fees
Nov 18 - Nov 19
Vantage Point Villas at Stratton Mountain Resort
Front of property
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3.0 star property
West Dover
8.8 out of 10, Excellent, (242)
"Free shuttle service to Dover is wonderful! Staff were friendly and helpful."
United States
Chris
The price is ￥22,692
￥27,158 total
includes taxes & fees
Nov 12 - Nov 13
Mount Snow Grand Summit Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Where to stay in Chester

Find the best Chester areas and neighborhoods 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.
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
aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Staff were fantastic "
Laurie 2-night trip
Posted 3 days ago
On The River Inn

More cheap stays in Chester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT
The price is ￥13,041 per night from Nov 11 to Nov 12
￥13,041
￥14,345 total
Nov 11 - Nov 12
includes taxes & fees
7.6/10 Good! (1,002 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 visit based on reviews is Fullerton Inn. 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?
Motel in the Meadow is a top pet-friendly option for your stay. Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub is another good option for a stay with 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. Jackson Gore Village and Kimpton Taconic Hotel by IHG 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 68 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 Grafton Historical Society and Vermont Country Store 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.

Explore a world of travel with Expedia