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Our top choices for Chester hotels

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (436 reviews)
"Beautiful old inn Great Staff"
United States
Elizabeth A
The price is Rp2.500.471
Rp2.725.513 total
includes taxes & fees
16 Jun - 17 Jun
Fullerton Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (118 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is Rp3.730.614
Rp4.066.369 total
includes taxes & fees
17 Jun - 18 Jun
Stone Hearth Inn and Eatery

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (447 reviews)
"The staff was very friendly and helpful."
Canada
Dumitru Florin
The price is Rp1.528.345
Rp1.681.252 total
includes taxes & fees
14 Jun - 15 Jun
Bromley View Inn

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (581 reviews)
"As a dog owner, this was the perfect stay. It is so convenient to have your car right there. The AC worked VERY well and the room was tidy, beautiful, and well kept. Everything worked great and appreciated the coffee in the morning! Just note you may not have great cell service, so knowing your room and code prior to arrival is very helpful to note down. Will definitely consider staying again!"
United States
Christine
The price is Rp1.152.375
Rp2.589.876 total
includes taxes & fees
24 Jun - 25 Jun
Sleep Woodstock Motel

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (991 reviews)
"The staff was very friendly."
United States
Steven
The price is Rp2.152.844
Rp2.368.129 total
includes taxes & fees
21 Jun - 22 Jun
Hampton Inn Brattleboro

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (512 reviews)
"Great stay and good location"
Canada
Alexandre
The price is Rp1.964.600
Rp2.131.591 total
includes taxes & fees
15 Jun - 16 Jun
Claremont Motor Lodge

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (40 reviews)
"The hot tub was so amazing"
United States
Mark
The price is Rp2.330.730
Rp2.540.496 total
includes taxes & fees
21 Jun - 22 Jun
Four Columns Inn

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (364 reviews)
"The bed was very comfortable! We had a great sleep and made our breakfast in the "snack room". It was pleasant and quiet- we sat on chairs out front looking at the mountain in front of us. It was a great place to stay."
United States
Susan
The price is Rp1.750.280
Rp1.925.308 total
includes taxes & fees
14 Jun - 15 Jun
Brittany Motel

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
3.0 star property
West Dover
8.6 out of 10, Excellent, (102 reviews)
"Newly renovated, clean, easy self check in, and great location!"
United States
Dana
The price is Rp1.594.005
Rp1.753.406 total
includes taxes & fees
1 Jul - 2 Jul
Hideaway Inn Mt. Snow

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,003 reviews)
"The staff was friendly, the room was clean and bed comfortable, the breakfast had a variety of options available. I’ll stay here again!"
United States
Dayna
The price is Rp1.946.740
Rp2.112.302 total
includes taxes & fees
14 Jun - 15 Jun
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, (862 reviews)
"Great place to stay"
United States
Daniel
The price is Rp2.700.432
Rp2.970.476 total
includes taxes & fees
16 Jun - 17 Jun
Best Western Springfield Hotel

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (815 reviews)
"Perfectly comfortable and convenient for us, and the complimentary breakfast buffet was better than most!"
United States
Bonnie
The price is Rp2.100.336
Rp2.310.369 total
includes taxes & fees
2 Jul - 3 Jul
Comfort Inn & Suites Brattleboro I-91

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (170 reviews)
"Self check-in and checkout. Room was very clean but a bit too much potpourri for my allergies. Will stay here again when in Keene. "
United States
Charles
The price is Rp2.486.648
Rp2.772.612 total
includes taxes & fees
15 Jun - 16 Jun
The Burrell House

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (118 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is Rp2.482.540
Rp2.730.794 total
includes taxes & fees
15 Jun - 16 Jun
Blue Gentian Lodge at Magic Mountain

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,002 reviews)
"We love staying here. It’s very clean, staff is always friendly,and the breakfast choices are great!!"
United States
Jennifer
The price is Rp2.128.912
Rp2.309.870 total
includes taxes & fees
16 Jun - 17 Jun
Best Western Plus Keene Hotel

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (129 reviews)
"Staff very helpful. Everything was very clean"
United States
Patrick
The price is Rp2.395.026
Rp2.634.528 total
includes taxes & fees
21 Jun - 22 Jun
Chalet 239

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,006 reviews)
"Great breakfast, friendly staff and good place to stay."
United States
Michael
The price is Rp1.578.824
Rp1.713.024 total
includes taxes & fees
18 Jun - 19 Jun
Days Inn by Wyndham Keene NH

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (900 reviews)
"Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!"
United States
Sharon
The price is Rp2.350.019
Rp2.585.056 total
includes taxes & fees
14 Jun - 15 Jun
Latchis Hotel

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, (996 reviews)
"Amazing hotel"
United States
Luis
The price is Rp2.661.140
Rp3.219.979 total
includes taxes & fees
21 Jun - 22 Jun
The Black Bear Lodge at Stratton Mountain Resort

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
The price is Rp2.833.268
Rp3.116.774 total
includes taxes & fees
24 Jun - 25 Jun
Colonel Williams Inn
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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

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.

A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

More cheap stays in Chester

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventure: Chester is perfect for ski enthusiasts and offers various outdoor activities amidst stunning natural scenery.
  • Cultural Experiences: Engage with local culture through agricultural exhibits, art galleries, and history museums.
  • Charming Accommodations: Enjoy a range of lodging options, from cosy bed & breakfasts to unique agritourism properties.
  • Picturesque Scenery: Experience the vibrant autumn colours and beautiful landscapes that enhance your visit.
  • Warm Hospitality: Delight in the friendly atmosphere and welcoming locals that make Chester a memorable destination.

Find great hotels near Chester

Discover the charming lodging options in Chester, Vermont, where a variety of accommodations await to suit every traveller's needs. Whether you prefer a cosy bed & breakfast or unique agritourism properties, you'll find affordable stays equipped with air conditioning and family-friendly amenities. Enjoy a delightful American breakfast and consider spacious suites for a comfortable retreat after your adventures in this picturesque locale.

  • The Upper Pass Lodge at Magic Mountain: Embrace the spirit of adventure at The Upper Pass Lodge at Magic Mountain, a pet-friendly motel located a mere 16.1km from Chester. This lodge is perfect for those seeking an action-packed getaway, offering a variety of exciting activities such as snowshoeing, ziplining, and fishing. Guests can enjoy the thrill of adventure sports right on their doorstep, making it an ideal choice for outdoor enthusiasts. The lodge also welcomes pets, providing amenities that ensure a comfortable stay for both you and your furry companions.
  • Main and Mountain Bar & Motel: Situated 17.7km from Chester, Main and Mountain Bar & Motel is a haven for adventure seekers. This motel features a laid-back atmosphere complemented by an array of recreational activities, including mountain biking, kayaking, and swimming. With its proximity to stunning natural landscapes, guests can easily explore the great outdoors and return to a welcoming environment. The combination of adventure and comfort makes this motel a perfect choice for those looking to immerse themselves in Vermont's natural beauty.
  • Castle Hill Resort And Spa: Experience a luxurious retreat at Castle Hill Resort And Spa, located just 14.5km from Chester. This 3.5-star hotel caters to travellers seeking both adventure and opulence. Guests can indulge in a variety of activities such as snowboarding, kayaking, and mountain biking, all while enjoying the resort's upscale amenities. With a focus on providing a high-end experience, Castle Hill combines relaxation and excitement, making it an exceptional choice for those wishing to unwind after a day of exploration.

Where to stay near Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation, making it an ideal destination for travellers seeking both excitement and tranquillity. Surrounded by charming towns and stunning natural scenery, visitors can enjoy outdoor activities like skiing and exploring historical sites. The vibrant autumn colours create a picturesque backdrop, inviting you to celebrate nature's beauty while experiencing the warm hospitality of the locals. Whether you're on a budget or seeking luxury, Chester has something for everyone.

  • Ludlow: Located approximately 17.7km from Chester, Ludlow is a vibrant city that attracts visitors year-round, peaking during the winter months from December to February. Renowned for its exceptional skiing and adventurous sports, Ludlow is a haven for outdoor enthusiasts. The nearby ski resorts and fields provide thrilling experiences, while the stunning landscapes of lakes, mountains, and valleys create a picturesque backdrop for exploration. Whether you're hitting the slopes or enjoying a quiet moment by the lake, Ludlow promises an exhilarating travel experience.
  • Springfield: Just 9.7km from Chester, Springfield is a charming city with a diverse array of attractions that draw visitors throughout the year. Peak seasons occur in February, July, and September, making it an appealing destination for adventure seekers. Springfield is known for its excellent skiing facilities and access to national state parks, offering a perfect blend of outdoor activities. The scenic beauty of the surrounding lakes and mountains adds to its allure, making Springfield a delightful spot for those seeking a mix of excitement and natural beauty.
  • Grafton: Situated a mere 9.7km from Chester, Grafton is a quaint city that offers a unique blend of outdoor adventure and serene landscapes. With peak visitor numbers in July and September to October, Grafton is ideal for those looking to enjoy skiing and outdoor activities amidst its stunning valleys and mountains. The welcoming atmosphere and beautiful surroundings make Grafton a fantastic choice for a peaceful retreat, where you can savour the beauty of nature while indulging in thrilling sports experiences.

Things to do near Chester

Chester, Vermont, offers a delightful blend of outdoor adventure and cultural attractions. Visitors can enjoy skiing at local resorts and engaging in various sports activities. Additionally, the town features agricultural exhibits, art galleries, and animal shows, making it perfect for day trips. Whether you're seeking adrenaline or a taste of local culture, Chester promises a memorable experience for all.

Shopping

In Chester, visit the Vermont Country Store and My Minds Design, both located 9.7km away, for charming gifts and souvenirs. If you're up for a drive, the West River Farmers Market, 17.7km away, offers a delightful selection of local produce and crafts in a vibrant atmosphere.

Recreation

At Crown Point Golf Course, enjoy a leisurely round of golf amidst picturesque landscapes, just 12.9km from Chester. Fox Run Golf Course, located 19.3km away, offers a vibrant sports atmosphere. For relaxation, visit The Ice House Ice Skating, 20.9km from Chester, where wellness and serenity await.

Adventure

Morningside Flight Park offers a breathtaking scenic flight experience, 19.3km from Chester, where you'll enjoy stunning views and a rush of adventure in the skies. For winter sports enthusiasts, Okemo Mountain Resort, located 17.7km away, provides excellent skiing opportunities amidst exhilarating snow-covered landscapes.

Nightlife

In Chester, the Weston Playhouse offers a charming theatre experience just 16.1km away, perfect for romance and culture. For an adventurous night, head to Maple Lanes, an arcadeAdventureZone 22.5km away, or try the Timber Ripper Mountain Coaster, located 20.9km from Chester for an exhilarating ride.

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

Booking tips and Expedia advantages for Chester

When planning your visit to Chester, Vermont, consider travelling in the cheaper months of April to May and November, with Tuesdays being the most affordable days to stay. Use Expedia’s search tool to filter for your budget and preferred accommodation, and sort by price to find the best deals. Look for package options that combine flights and hotels for additional savings. To explore the area on a budget, seek out free local activities and utilise public transport whenever possible to keep costs down.

  • 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. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save money by combining your hotel reservation in Chester with your flights and activities through an Expedia package.

Find the best attractions near Chester

Chester, Vermont, is perfect for ski enthusiasts and adventure seekers, offering a variety of outdoor activities and cultural experiences. Visitors can explore local parks, national and state parks, and history museums, making it an ideal destination for families and those interested in the region's heritage. Whether you're keen on sports or simply wish to enjoy the natural beauty, Chester has something for everyone.

  • Vermont Museum of Mining and Minerals: Located 9.7km from Chester, this museum offers a fascinating glimpse into the region's mining history. Visitors can explore various exhibits showcasing minerals and mining artefacts, making it an enriching experience for families and culture enthusiasts alike.
  • Lowell Lake State Park: Situated 14.5km away, this national park is a haven for outdoor lovers. With its stunning scenery and numerous trails, visitors can enjoy hiking, kayaking, and picnicking amidst breathtaking natural beauty, perfect for adventure seekers.
  • Grafton Historical Society: Just 9.7km from Chester, this history museum presents the rich cultural heritage of the area. Through engaging exhibits and local artefacts, visitors can delve into the history of Grafton and its significance in Vermont.

Best time to go to Chester

The best time to visit Chester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

For your visit to Chester, Vermont, you have several nearby airports to consider. Lebanon Municipal Airport (LEB) is 46.7km away, with hotels like the Windsor Mansion Inn, Residence Inn by Marriott Hanover Lebanon, and Sunset Motor Inn, all offering convenient access. Rutland Southern Vermont Regional Airport (RUT) is 40.2km away, featuring options such as Cortina Inn and Killington Mountain Lodge, which provide shuttle services. Additionally, Hartness State Airport (VSF) is just 11.3km from Chester, with nearby accommodations including the 4-star Inn at Weathersfield and Castle Hill Resort And Spa. Each airport ensures a variety of transport options to facilitate your journey.

Frequently asked questions

Where is the best place to stay in Chester?
Based on our traveller data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. Other good choices for your stay in the area are Woodstock Inn & Resort and Kimpton Taconic Hotel by IHG. 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: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. Kimpton Taconic Hotel by IHG and Hampton Inn Brattleboro 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 62 hotels and other accommodation options to choose from. Find out more about Chester.
What should I do while I'm visiting Chester?
Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are fun for everyone. You'll also find Vermont Country Store and Lowell Lake State Park 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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