Find hotels in Chester, VT from ￥14,237

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Dec 26 - Dec 27
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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 ￥32,573
￥35,505 total
includes taxes & fees
Dec 29 - Dec 30
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 ￥20,116
￥21,926 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Fullerton Inn
Interior
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 ￥20,548
￥22,603 total
includes taxes & fees
Jan 4 - Jan 5, 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 savor 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
Premium bedding, individually decorated, individually furnished, desk
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 center or unwind with a drink at the bar after exploring nearby attractions.
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ￥21,676
￥23,519 total
includes taxes & fees
Dec 28 - Dec 29
Best Western Plus Keene Hotel
Indoor pool
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, (968)
Escape to this quiet retreat with an indoor pool and fitness center 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 travelers.
"The room was perfect, and the food was great "
United States
Paul
The price is ￥18,370
￥19,932 total
includes taxes & fees
Dec 28 - Dec 29
Keene Elm City Hotel, an Ascend Collection Hotel
Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed) | Laptop workspace, iron/ironing board, rollaway beds, free WiFi
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 center. 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 ￥23,720
￥26,093 total
includes taxes & fees
Jan 5 - Jan 6, 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 ￥28,069
￥30,455 total
includes taxes & fees
Jan 1 - Jan 2, 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
Reception
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, (1001)
Stylish accommodations in Keene Downtown, 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 ￥28,069
￥30,455 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Courtyard by Marriott Keene Downtown
Meeting facility
Aspen At Manchester

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (613)
This Manchester Center 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 ￥15,493
￥18,756 total
includes taxes & fees
Jan 4 - Jan 5, 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, (1002)
Step into comfort at this Manchester Center 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 ￥20,331
￥22,365 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn and Suites Manchester
Interior
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 transportation, 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 ￥26,462
￥29,108 total
includes taxes & fees
Dec 30 - Dec 31
The Hartness House
Property grounds
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 Center 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.
"Staff and room was clean "
United States
Melissa
The Manchester View
Exterior
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 Center 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 ￥15,773
￥19,920 total
includes taxes & fees
Jan 15 - Jan 16, 2026
The Palmer House Resort, an Ascend Collection Hotel
Seasonal outdoor pool
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 ￥35,087
￥38,596 total
includes taxes & fees
Jan 2 - Jan 3, 2026
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 Center 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 ￥28,849
￥31,734 total
includes taxes & fees
Jan 4 - Jan 5, 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 Center 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 ￥22,299
￥24,529 total
includes taxes & fees
Jan 4 - Jan 5, 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, (156)
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 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

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

The Jackson

The Jackson

10/10 Excellent
"The staff was absolutely lovely. The Inn has a complimentary wine and cheese spread from 1730-1830. The hotel staff is on hand and its a great way to get to know fellow travelers and the staff themselves. My friend and I went both nights we were there and talked with Dave, one of the owners and the second night we spoke with Shawn (spelling?) We talked of books and going to Connecticut, to Yale and Mystic for Pizza. "
Nicole 2-night trip
Posted 1 day ago
The Jackson

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 ￥13,122 per night from Dec 31 to Jan 1
￥13,122
￥14,237 total
Dec 31 - Jan 1, 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 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?
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: Visitors like this Chester vacation home rental. It is located on the waterfront and has a balcony, a garden, 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. Kick off your shoes and enjoy yourself with a selection of games and a hot tub. 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 Bonnie's Bundles Dolls and DaVallia Art & Accents 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. Pointe at Castle Hill Resort and Grand Summit Resort, A Vail Resorts Property 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. A top sight in the area is Stratton Mountain Resort. 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. Additionally, you'll find Stratton Mountain Resort 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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