Chester Hotels

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Our top choices for Chester hotels

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is P12,268
P13,372 total
includes taxes & fees
Dec 29 - Dec 30
Stone Hearth Inn and Eatery

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (403)
"Lovely stay"
United States
Christine
The price is P7,576
P8,258 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Fullerton Inn

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 P7,938
P8,731 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hideaway Inn Mt. Snow

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
"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

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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is P8,164
P8,858 total
includes taxes & fees
Dec 28 - Dec 29
Best Western Plus Keene 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)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is P7,198
P7,810 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Keene Elm City Hotel, an Ascend Collection Hotel

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (806)
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is P8,934
P9,827 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Best Western Springfield Hotel

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 P10,572
P11,470 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fairfield Inn & Suites by Marriott Keene Downtown

Brook Bound Inn

Brook Bound Inn
2.0 star property
Wilmington
9.6 out of 10, Exceptional, (11)
"Great property. Amazing views!"
United States
Ryan
Brook Bound Inn

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1001)
"Very comfortable and clean."
United States
Christina
The price is P10,572
P11,470 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Courtyard by Marriott Keene Downtown

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (613)
"Super clean and modern rooms, excellent location, scenic views… "
United States
Fernando
The price is P5,835
P7,064 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Aspen At Manchester

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1002)
"Great time "
United States
Paul
The price is P7,657
P8,423 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn and Suites Manchester

The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very Good, (329)
"nice folks, practical place to stay. "
United States
Mark
The price is P10,911
P12,002 total
includes taxes & fees
Dec 31 - Jan 1, 2026
The Hartness House

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (782)
"Staff and room was clean "
United States
Melissa
The Manchester View

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)
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
United States
Amanda
The price is P5,941
P7,503 total
includes taxes & fees
Jan 15 - Jan 16, 2026
The Palmer House Resort, an Ascend Collection Hotel

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 P13,215
P14,536 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Inn At Quail Run

The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (563)
"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 P10,865
P11,952 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Olympia Lodge

Toll Road Inn

Toll Road Inn
2.0 star property
Manchester Center
9.0 out of 10, Wonderful, (489)
"Clean and convenient room, good experience."
United States
Mingyang
The price is P8,399
P9,239 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Toll Road Inn

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156)
"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

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.

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

Top Chester Hotel Reviews

More cheap stays in Chester

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester offers a plethora of opportunities for skiing and winter sports, making it a prime destination for adventure enthusiasts.
  • Charming Downtown: Explore the quaint downtown area filled with quirky shops, providing a unique shopping experience.
  • Cultural Experiences: Discover local history through museums and state parks, blending cultural enrichment with outdoor activities.
  • Relaxing Getaway: The town's friendly atmosphere and delightful lodging options make it perfect for a weekend retreat.
  • Pet-Friendly Options: Chester caters to all, including pet lovers, ensuring a welcoming experience for every traveller.

Find great hotels near Chester

Explore the delightful lodging options in Chester, Vermont, where you can choose from charming bed and breakfasts to unique agritourism properties. Catering to families, adventurers, and pet lovers alike, this picturesque area offers a variety of hotel services and facilities to ensure a memorable stay. Whether seeking hotel reviews or comfortable rooms, Chester promises an inviting retreat in the heart of New England.

  • Best Western Springfield Hotel: Nestled 12.9km from Chester, Best Western Springfield Hotel is a welcoming retreat ideal for pet lovers. This hotel embraces a pet-friendly ethos, allowing dogs to accompany their owners, making it perfect for those who prefer to travel with their furry friends. Guests appreciate the warm, comfortable atmosphere and the attentive service, which ensures a pleasant stay. Key amenities include a relaxing environment and convenient access to local attractions, making it a great choice for families and couples alike.
  • Pointe at Castle Hill Resort: Situated 14.5km from Chester, this 3.5-star rated hotel offers a blend of business and adventure with a touch of luxury. The Pointe at Castle Hill Resort boasts an extensive range of adventure sports, including skiing, horse riding, hiking, and zip-lining, perfect for thrill-seekers. After an action-packed day, guests can unwind at the full-service spa, offering treatments and an indoor pool. With its focus on relaxation and adventure, this resort is a fantastic choice for those looking to balance work and play.
  • Jackson Gore Village: Located 20.9km from Chester, Jackson Gore Village is a family-friendly haven designed for both adventure and relaxation. This 3-star rated property features ample activities for children, including a playground, mini-golf, and arcade game room, ensuring a delightful experience for younger guests. Adventure enthusiasts can enjoy onsite zip-lining and ski lessons, along with nearby hiking and snow tubing. Families will appreciate the welcoming atmosphere and spacious accommodations, making it an excellent choice for creating lasting holiday memories.

Where to stay near Chester

Chester, Vermont, is a charming destination perfect for a weekend getaway, offering a delightful blend of relaxation and adventure. Visitors can explore the quaint downtown area, indulge in recreational opportunities, and soak in the friendly atmosphere. Nearby regions provide a taste of luxury and historical charm, making it an ideal spot for travellers seeking both budget-friendly experiences and thrilling outdoor activities. Whether skiing or unwinding, Chester promises an unforgettable escape.

  • Ludlow: Nestled 17.7km from Chester, Ludlow is a vibrant city renowned for its outdoor adventures, especially in the winter months when skiing takes centre stage. The travel experience here is characterised by a mix of seasonal excitement, with visitor numbers peaking from December to February. Ludlow's picturesque landscape features stunning lakes, majestic mountains, and serene valleys, making it a perfect backdrop for skiing and sports enthusiasts. Popular venues include ski resorts that cater to both novices and experts alike, offering thrilling slopes and breathtaking views.
  • Springfield: Located a mere 9.7km from Chester, Springfield is a charming city that attracts visitors year-round with its diverse offerings. Known for its skiing and adventure sports, it sees a surge of tourists in February, July, and September. The city is surrounded by natural beauty, including lakes, mountains, and the nearby national state park, providing ample opportunities for exploration and outdoor activities. Whether you're seeking adrenaline-pumping experiences or tranquil moments in nature, Springfield has something for everyone.
  • Grafton: Just 9.7km from Chester, Grafton is a delightful city that combines outdoor adventure with serene landscapes. With a steady stream of visitors, particularly in July and the autumn months, Grafton is a prime destination for those looking to ski and enjoy the great outdoors. The area is dotted with enchanting lakes, valleys, and mountains, perfect for hiking or simply soaking in the stunning scenery. Grafton’s welcoming atmosphere and access to ski resorts make it an ideal spot for adventure seekers looking for both excitement and relaxation.

Things to do near Chester

Chester, Vermont, is a delightful destination for those seeking outdoor adventures and winter sports. Visitors can indulge in skiing at nearby resorts and explore various ski fields. Additionally, the town boasts quirky shops that offer a unique shopping experience, making it an ideal spot for a memorable holiday filled with both excitement and charm.

Shopping

For a delightful shopping experience in Chester, visit the Vermont Country Store and My Minds Design, both located 9.7km away. If you're up for a drive, head to the West River Farmers Market, situated 17.7km from Chester, offering a vibrant local atmosphere and unique finds.

Recreation

The Ice House Ice Skating, located 20.9km from Chester, offers a refreshing experience with its wellness and relaxation vibes, perfect for a leisurely day. Crown Point Golf Course, 12.9km away, invites you to enjoy outdoor sports in a picturesque setting, while Fox Run Golf Course, 19.3km distant, promises a delightful round amidst nature.

Adventure

Experience the thrill of skiing at Okemo Mountain Resort, located 17.7km from Chester, where you can enjoy a variety of slopes. For a unique ride, the Skywalker Carpet ski lift, also 17.7km away, offers easy access to the slopes. Don't miss the Tubing Park, 20.9km away, for exhilarating outdoor fun.

Nightlife

Experience the charm of the Weston Playhouse, a theatre 16.1km from Chester, offering delightful performances. For family fun, visit Maple Lanes, an arcade adventure zone 22.5km away. For thrill-seekers, try the Timber Ripper Mountain Coaster, an exhilarating ride located 20.9km from Chester.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chester

For a budget-friendly trip to Chester, Vermont, consider visiting during the cheaper months of April to May and November, avoiding the peak seasons of January to February and October. Book your stay on a Tuesday for the best rates and use Expedia's search tool to filter by budget and eco-friendly accommodations. Combine hotel, flight, and activity bookings for additional savings through package deals. Explore free local attractions and utilise public transport options to minimise travel expenses while enjoying the scenic beauty of Chester.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are April to May and November, where the prices are slightly lower. This is in comparison to January to February and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Friday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Chester with your flights and activities through an Expedia package deal.

Find the best attractions near Chester

Chester, Vermont, is an ideal destination for skiing and adventure sports enthusiasts. Visitors can explore a variety of points of interest, including parks, state parks, and history museums, offering a rich blend of outdoor activities and cultural experiences. Whether you're seeking family-friendly adventures or a taste of local history, Chester provides a delightful array of attractions to suit every traveller's needs.

  • Hunter Gallery of Fine Art: Located 9.7km from Chester, this gallery showcases a diverse array of artworks, embodying a rich cultural atmosphere. Visitors can immerse themselves in the local art scene and engage with talented artists, making it a perfect spot for art enthusiasts.
  • The Nature Museum: Also situated 9.7km away, this eco-friendly centre offers an interactive experience focusing on environmental conservation. It features exhibits that highlight the region's natural history, making it ideal for those keen on sustainability and nature education.
  • General Parking: Though 17.7km from Chester, this landmark is vital for visitors, providing convenient access to various attractions in the area, ensuring a hassle-free exploration.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.7°F (-6.3°C)Light RainMostly CloudySlightly LowSlightly High
February22.6°F (-5.2°C)Light RainMostly CloudySlightly LowSlightly High
March30.7°F (-0.7°C)Light RainMostly CloudySlightly LowAverage
April42.8°F (6.0°C)Light RainMostly CloudyAverageSlightly Low
May55.8°F (13.2°C)Light RainMostly SunnyAverageSlightly Low
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnySlightly HighAverage
August67.3°F (19.6°C)Light RainMostly SunnySlightly HighAverage
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
October48.6°F (9.2°C)Light RainMostly SunnyAverageSlightly High
November36.1°F (2.3°C)Light RainMostly SunnyAverageSlightly Low
December27.3°F (-2.6°C)Light RainMostly CloudyAverageAverage

The nearest major airports for your trip to Chester

When visiting Chester, Vermont, you have several airport options. Rutland Southern Vermont Regional Airport (RUT) is located 40.2km away, with nearby hotels like the 3-star Cortina Inn and Days Inn by Wyndham, both offering free 24-hour airport shuttle services. Glens Falls Airport (GFL) is 82.1km from Chester, with lodgings such as the 4-star Lodges At Cresthaven and the 3.5-star Six Flags Great Escape Lodge, providing accessible shuttle services for a fee. Additionally, Lebanon Municipal Airport (LEB) is 46.7km away, and options like the Windsor Mansion Inn and Courtyard by Marriott Hanover Lebanon are conveniently located nearby, offering easy access to the airport.

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.
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.
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. 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 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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