Find hotels in Chester, VT from ฿2,840

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24 Dec - 25 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Chester hotels

Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
This charming B&B offers free WiFi and parking with a daily buffet breakfast. Outdoor enthusiasts will love the nearby hiking trails and mountain biking, while popular attractions like Bonnie's Bundles Dolls are just minutes away.
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is ฿6,497
฿7,082 total
includes taxes & fees
29 Dec - 30 Dec
Stone Hearth Inn and Eatery
Garden
Fullerton Inn

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (403)
Experience small-town allure at this Chester inn with free breakfast, WiFi, and parking. Grab a drink at the bar, dine at the restaurant, and explore nearby DaVallia Art and Bonnie's Bundles Dolls. Guests rave about the clean rooms and helpful staff.
"Lovely stay"
United States
Christine
The price is ฿4,013
฿4,374 total
includes taxes & fees
7 Jan - 8 Jan 2026
Fullerton Inn
Property amenity
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (4)
"Really happy with our stay and the way we felt at this hideaway "
United States
Edwin
The price is ฿4,204
฿4,624 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hideaway Inn Mt. Snow
Interior
The Inn at Weathersfield

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
This inviting Perkinsville inn offers free Wi-Fi, breakfast and parking. Unwind with drinks at the bar/lounge or savour a meal at the restaurant. North Springfield Lake and Stoughton Pond Recreation Areas await nearby.
"The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. "
United States
Joshua
The Inn at Weathersfield
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1001)
"The room was okay for a quick stop to rest. "
United States
Janice
The Putney Inn
Restaurant
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1001)
This hotel offers quiet rooms and a peaceful environment near the Ashuelot River. Enjoy complimentary breakfast, WiFi, and parking. Guests love the helpful staff and convenient location. Visit the 24-hour fitness centre or unwind with a drink at the bar after exploring nearby attractions.
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ฿4,324
฿4,691 total
includes taxes & fees
29 Dec - 30 Dec
Best Western Plus Keene Hotel
Lobby
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (967)
Escape to this quiet retreat with an indoor pool and fitness centre near Ashuelot River. Just minutes from local shops and eateries, this hotel offers free breakfast, WiFi, and parking. The helpful staff ensures a comfortable stay for business or leisure travellers.
"The room was perfect, and the food was great "
United States
Paul
The price is ฿3,664
฿3,976 total
includes taxes & fees
28 Dec - 29 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior
Best Western Springfield Hotel

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (806)
Tucked away in Springfield, this tranquil hotel offers a refreshing indoor swimming experience and fitness centre. Guests can explore nearby Baltimore Covered Bridge while enjoying free breakfast, WiFi, and parking throughout their stay.
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is ฿4,732
฿5,205 total
includes taxes & fees
7 Jan - 8 Jan 2026
Best Western Springfield Hotel
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
The price is ฿5,599
฿6,075 total
includes taxes & fees
7 Jan - 8 Jan 2026
Fairfield Inn & Suites by Marriott Keene Downtown
Family Cabin | Living area | 30-inch LCD TV with cable channels
Brook Bound Inn

Brook Bound Inn

Brook Bound Inn
2.0 star property
Wilmington
9.6 out of 10, Exceptional, (11)
Brook Bound Inn offers a charming Vermont retreat just minutes from Mount Snow. Enjoy snowmobiling on-site, then relax in the seasonal outdoor pool. With free WiFi and parking, this golf hotel puts North Branch Deerfield River adventures within easy reach.
"Great property. Amazing views!"
United States
Ryan
Brook Bound Inn
Pub
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1002)
Stylish accommodation in Keene City centre, close to Colonial Theatre and Central Square. Enjoy a refreshing swim in the indoor pool, grab a bite at the coffee shop, then unwind at the bar. Free WiFi and parking make exploring the area convenient.
"Very comfortable and clean."
United States
Christina
The price is ฿5,599
฿6,075 total
includes taxes & fees
31 Dec - 1 Jan 2026
Courtyard by Marriott Keene Downtown
Reception
Aspen At Manchester

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (613)
This Manchester Centre hotel offers a seasonal outdoor pool and free bike rentals to explore nearby hiking trails. Just minutes from Bromley Mountain for skiing enthusiasts, with complimentary WiFi and parking. Guests praise the helpful staff and clean, comfortable rooms.
"Super clean and modern rooms, excellent location, scenic views… "
United States
Fernando
The price is ฿3,091
฿3,741 total
includes taxes & fees
5 Jan - 6 Jan 2026
Aspen At Manchester
Front of property – evening/night
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1000)
Step into comfort at this Manchester Centre hotel, just minutes from shopping destinations. The indoor pool and hot tub offer year-round relaxation, while rooms include convenient refrigerators and microwaves. Enjoy complimentary breakfast, WiFi, and parking before exploring nearby attractions.
"Great time "
United States
Paul
The price is ฿4,056
฿4,461 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn and Suites Manchester
Lobby sitting area
The Hartness House

The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very good, (329)
Beautifully situated with easy access to transport, this charming hotel offers free WiFi and parking. Outdoor enthusiasts will appreciate nearby hiking trails, kayaking, and mountain biking opportunities, with Muckross State Park just a short drive away.
"nice folks, practical place to stay. "
United States
Mark
The price is ฿5,706
฿6,277 total
includes taxes & fees
25 Dec - 26 Dec
The Hartness House
Porch
The Manchester View

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (782)
Surrounded by Green Mountains, this Manchester Centre hotel offers a seasonal outdoor pool and free breakfast. Hike nearby trails or enjoy skiing at Bromley Mountain. Spacious rooms provide comfort after exploring Dana L. Thompson Memorial Park.
"Room very clean comfortable and quiet "
United States
Patty
The Manchester View
Property amenity
The Palmer House Resort, an Ascend Collection Hotel

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, (866)
Surrounded by Vermont's natural beauty, this Manchester Centre hotel offers a golf course minutes from Bromley Mountain Ski Resort. Guests enjoy the hot tub, American dining at Clove + Maple, and complimentary breakfast while exploring nearby Lye Brook Falls.
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
United States
Amanda
The price is ฿3,146
฿3,974 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Palmer House Resort, an Ascend Collection Hotel
Exterior
The Inn At Quail Run

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (71)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is ฿5,447
฿5,991 total
includes taxes & fees
25 Dec - 26 Dec
The Inn At Quail Run
Interior
The Olympia Lodge

The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (563)
Surrounded by Vermont's beauty, this Manchester Centre lodge offers a refreshing seasonal pool and outdoor tennis court. Enjoy free breakfast, parking, and WiFi while being close to Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park.
"Great little inn. Has a wonderful home feeling. The owners are super friendly and made the stay a great experience."
United States
Holly
The price is ฿5,755
฿6,330 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Olympia Lodge
Lobby sitting area
Toll Road Inn

Toll Road Inn

Toll Road Inn
2.0 star property
Manchester Center
9.0 out of 10, Wonderful, (489)
This charming hotel offers a seasonal outdoor pool and relaxing hot tub after mountain adventures. Located in Manchester Centre with free WiFi and parking, it's just a short drive to Bromley Mountain and Gander Gallery.
"Clean and convenient room, good experience."
United States
Mingyang
The price is ฿4,448
฿4,893 total
includes taxes & fees
5 Jan - 6 Jan 2026
Toll Road Inn
Exterior
The Burrell House

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
Walking distance to Central Square, this inviting guesthouse offers complimentary WiFi and self parking. Enjoy the outdoor picnic area after exploring nearby attractions like CC&H Framing and Pepper Pete's Hot Shop.
"Very helpful, kind staff"
United States
Paitris
The Burrell House
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

Bonnie's Bundles Dolls

Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views or seek out its ski slopes.
See properties

DaVallia Art & Accents

Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"I arrived far before published check-in time and only had to wait a reasonable amount of time to get into my room. Desk clerks were efficient and friendly. Clean, comfortable room. "
Wick 1-night trip
Posted 6 days ago
Comfort Inn & Suites Brattleboro I-91

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is ฿2,618 per night from 31 Dec to 1 Jan
฿2,618
฿2,840 total
31 Dec - 1 Jan 2026
includes taxes & fees
7/10 Good! (999 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 Grand Summit Resort, A Vail Resorts Property 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. A top sight in the area is Stratton Mountain Resort. 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. Additionally, you'll find Stratton Mountain Resort 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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