Find hotels in Chester, VT from Rp1.473.771

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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, (402)
"Lovely stay"
United States
Christine
The price is Rp2.147.334
Rp2.340.594 total
includes taxes & fees
16 Dec - 17 Dec
Fullerton Inn

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 Rp3.477.033
Rp3.789.966 total
includes taxes & fees
16 Dec - 17 Dec
Stone Hearth Inn and Eatery

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (554)
"Highly recommend stay here"
United States
Margie
The price is Rp5.642.994
Rp6.939.718 total
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (606)
"Great place to stay"
United States
Brian
The price is Rp2.069.712
Rp2.459.623 total
includes taxes & fees
8 Jan - 9 Jan 2026
Aspen At Manchester

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (893)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock

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, (864)
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
United States
Amanda
The price is Rp1.782.787
Rp2.235.559 total
includes taxes & fees
21 Dec - 22 Dec
The Palmer House Resort, an Ascend Collection Hotel

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 Rp2.223.906
Rp2.446.296 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn and Suites Manchester

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is Rp1.288.400
Rp2.732.274 total
includes taxes & fees
14 Dec - 15 Dec
Sleep Woodstock Motel

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, (940)
"We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses."
United States
Mark
The price is Rp3.079.510
Rp3.726.374 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Black Bear Lodge at Stratton Mountain Resort

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (927)
"Great place to stay while skiing at okemo"
United States
Ken
The price is Rp2.813.174
Rp3.207.018 total
includes taxes & fees
16 Dec - 17 Dec
Pointe at Castle Hill Resort

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (576)
"Beautiful hotel! "
United States
sarah
The price is Rp3.137.717
Rp4.395.213 total
includes taxes & fees
18 Dec - 19 Dec
The Equinox Golf Resort & Spa

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)
"Amazing stay - The condo was cozy and perfect for our family! "
United States
Kate
The price is Rp5.077.030
Rp6.310.749 total
includes taxes & fees
14 Dec - 15 Dec
Vantage Point Villas at Stratton Mountain Resort

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
"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 Rp1.318.363
Rp1.450.200 total
includes taxes & fees
22 Dec - 23 Dec
The Covered Bridge Inn

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
4.0 star property
Manchester Village Historic District
9.4 out of 10, Exceptional, (817)
"Very nice, beautiful inn"
United States
Susan
The price is Rp2.820.745
Rp3.744.845 total
includes taxes & fees
14 Dec - 15 Dec
Kimpton Taconic Hotel by IHG

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (776)
"Room was beautiful and the staff was nice. The view is a little piece if heaven."
United States
Amanda
The Manchester View

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort
3.0 star property
West Dover
8.8 out of 10, Excellent, (243)
"Great place to stay!"
United States
Sonia
The price is Rp3.722.545
Rp4.455.187 total
includes taxes & fees
15 Dec - 16 Dec
Mount Snow Grand Summit Resort

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (778)
"Clean room, very nice staff, everything was excellent! "
United States
Karen
The price is Rp1.980.874
Rp2.431.315 total
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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, (1000)
"Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. "
United States
Belinda
The price is Rp2.397.024
Rp2.636.726 total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Jackson Gore Village

Jackson Gore Village
3.0 star property
Jackson Gore Base Area
8.6 out of 10, Excellent, (838)
"great location"
Canada
Patrice
The price is Rp5.949.613
Rp7.228.558 total
includes taxes & fees
13 Jan - 14 Jan 2026
Jackson Gore Village

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (86)
"We had a lovely time staying here. "
United States
Jeff
Deerfield Valley 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, Bonnie's Bundles Dolls and DaVallia Art & Accents 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 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?
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. The Equinox Golf Resort & Spa and Kimpton Taconic Hotel by IHG 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 68 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 DaVallia Art & Accents and Bonnie's Bundles Dolls. 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.