Find hotels in Chester, VT from NT$2,761

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Our top choices for Chester hotels

Fullerton Inn

2.5 star property
Chester Depot
8.2 out of 10, Very Good, (402)
"Lovely stay"
United States
Christine
The price is NT$4,022
NT$4,385 total
includes taxes & fees
Dec 11 - Dec 12
Fullerton Inn

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 NT$6,513
NT$7,100 total
includes taxes & fees
Dec 11 - Dec 12
Stone Hearth Inn and Eatery

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (553)
"Highly recommend stay here"
United States
Margie
The price is NT$10,571
NT$13,000 total
includes taxes & fees
Dec 16 - Dec 17
Woodstock Inn & Resort

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 NT$3,877
NT$4,607 total
includes taxes & fees
Jan 8 - 2026/1/9
Aspen At Manchester

The Palmer House Resort, an Ascend Collection Hotel

3.0 star property
Manchester Center
8.4 out of 10, Very Good, (863)
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
United States
Amanda
The price is NT$3,340
NT$4,188 total
includes taxes & fees
Dec 16 - Dec 17
The Palmer House Resort, an Ascend Collection Hotel

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (889)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock

Hampton Inn and Suites Manchester

2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1001)
"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 NT$3,966
NT$4,363 total
includes taxes & fees
Jan 4 - 2026/1/5
Hampton Inn and Suites Manchester

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (548)
"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 NT$2,413
NT$5,118 total
includes taxes & fees
Dec 11 - Dec 12
Sleep Woodstock Motel

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
Stratton
7.6 out of 10, Good, (939)
"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 NT$5,769
NT$6,980 total
includes taxes & fees
Jan 5 - 2026/1/6
The Black Bear Lodge at Stratton Mountain Resort

Pointe at Castle Hill Resort

3.5 star property
Cavendish
8.8 out of 10, Excellent, (923)
"Great place to stay while skiing at okemo"
United States
Ken
The price is NT$5,270
NT$6,008 total
includes taxes & fees
Dec 11 - Dec 12
Pointe at Castle Hill Resort

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (576)
"Beautiful hotel! "
United States
sarah
The price is NT$5,112
NT$7,357 total
includes taxes & fees
Dec 11 - Dec 12
The Equinox Golf Resort & Spa

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 NT$9,199
NT$11,434 total
includes taxes & fees
Dec 11 - Dec 12
Vantage Point Villas at Stratton Mountain Resort

Kimpton Taconic Hotel by IHG

4.0 star property
Manchester
9.4 out of 10, Exceptional, (817)
"Very nice, beautiful inn"
United States
Susan
The price is NT$4,708
NT$6,380 total
includes taxes & fees
Jan 5 - 2026/1/6
Kimpton Taconic Hotel by IHG

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 NT$2,470
NT$2,717 total
includes taxes & fees
Dec 13 - Dec 14
The Covered Bridge Inn

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
Brownsville
9.0 out of 10, Wonderful, (777)
"Very welcoming, spacious, clean. Perfect for a family of 4. "
United States
Kathleen
The price is NT$3,711
NT$4,554 total
includes taxes & fees
Dec 15 - Dec 16
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

The Manchester View

2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (775)
"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

3.0 star property
West Dover
8.8 out of 10, Excellent, (243)
"Great place to stay!"
United States
Sonia
The price is NT$4,954
NT$5,929 total
includes taxes & fees
Dec 11 - Dec 12
Mount Snow Grand Summit Resort

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 NT$9,317
NT$11,320 total
includes taxes & fees
Dec 11 - Dec 12
Jackson Gore Village

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

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 NT$4,490
NT$4,939 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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. Learn more about Chester
Learn more about Chester

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

Hotels in Chester with star-rating

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester offers excellent skiing options and a variety of outdoor activities, perfect for adventure seekers.
  • Charming Downtown: Stroll through Chester's historic streets filled with quirky shops and a vibrant atmosphere.
  • Cultural Experiences: Explore local parks, historical museums, and engage with friendly locals for a rich cultural experience.
  • Family-Friendly Accommodations: Enjoy a range of lodging options, from cozy bed and breakfasts to unique agritourism properties.
  • Budget-Friendly Options: Chester provides affordable recreational opportunities, ensuring a memorable vacation for every traveler.

Find great hotels near Chester

Discover the charm of Chester, Vermont, where a variety of lodging options await you, including cozy bed and breakfasts and unique agritourism properties. Perfect for families, adventurers, and pet lovers, Chester's hotels offer the ideal retreat with essential amenities and warm hospitality. Explore local hotel reviews to find the perfect fit for your stay and enjoy a memorable vacation experience in this picturesque New England town.

  • Best Western Springfield Hotel: This welcoming hotel offers a pet-friendly experience, making it ideal for travelers who wish to bring their furry companions along. Located 12.9km from Chester, the Best Western Springfield Hotel features comfortable accommodations with amenities designed for both relaxation and convenience. Guests appreciate the hotel's accommodating pet policy, which allows dogs on the property. With a focus on providing a friendly and accessible atmosphere, this hotel is perfect for those looking to explore the scenic beauty of Vermont while enjoying the company of their pets.
  • Pointe at Castle Hill Resort: A 3.5-star gem situated 14.5km from Chester, this resort embodies adventure and relaxation. With a plethora of onsite and nearby activities, including snow tubing, ziplining, and mountain biking, guests will find plenty of excitement. After an action-packed day, unwind at the full-service spa, where treatments like aromatherapy and deep tissue massage await. Perfect for business travelers and thrill-seekers alike, the Pointe at Castle Hill Resort combines comfort with a touch of adventure, making it a distinctive choice for your stay.
  • Jackson Gore Village: Nestled 20.9km from Chester, Jackson Gore Village is a family-friendly retreat that offers a unique blend of adventure and leisure. Guests can enjoy a variety of activities, including onsite snow tubing and skiing, as well as family-friendly amenities like a mini-golf course and playground. This 3-star accommodation is perfect for families seeking fun and excitement together. The focus on adventure and community makes Jackson Gore Village an attractive destination for those looking to create lasting memories in the beautiful Vermont landscape.

Where to stay near Chester

Chester, Vermont, is a charming destination perfect for a weekend getaway, offering a mix of relaxation and adventure. Explore downtown Chester's historic streets and vibrant atmosphere, where friendly locals welcome you. Enjoy recreational opportunities like skiing and various outdoor activities, all while appreciating the town's budget-friendly options. Whether you're seeking luxury or a laid-back vibe, Chester has something for every traveler, making it an ideal spot for your vacation.

  • Ludlow: Located 17.7km from Chester, Ludlow is a vibrant city known for its seasonal charm, particularly during the winter months when outdoor enthusiasts flock to its ski resorts. With a strong emphasis on adventure, Ludlow offers thrilling opportunities for skiing and other winter sports against a backdrop of picturesque mountains and valleys. Visitors can explore the nearby lakes, making it a perfect spot for both ski lovers and nature enthusiasts. The ski fields here are easily accessible, providing a fun-filled experience for travelers of all skill levels.
  • Springfield: Just 9.7km from Chester, Springfield is a year-round destination that attracts visitors with its diverse outdoor activities. The city sees peaks in travel during February, July, and September, drawing those eager for both skiing and exploration. With proximity to national state parks, lakes, and mountains, Springfield offers a rich landscape for hiking, skiing, and other outdoor adventures. Its vibrant community and local attractions make it a delightful stop for anyone looking to immerse themselves in the beauty of Vermont.
  • Grafton: Also located 9.7km from Chester, Grafton is a charming city that shines in the summer and early fall months, welcoming travelers seeking outdoor experiences. Known for its scenic ski fields and lush valleys, Grafton is ideal for those wanting to embrace nature year-round. The area’s stunning lakes and mountainous terrain provide a beautiful backdrop for an array of activities, including hiking, skiing, and simply enjoying the fresh Vermont air. Grafton's quaint atmosphere and outdoor offerings make it a must-visit for adventurers.

Things to do near Chester

Chester, Vermont is the perfect destination for adventure seekers and ski enthusiasts. Enjoy outdoor adventures in the scenic landscape, explore quirky shops that offer unique finds, and take advantage of the excellent skiing options available at local ski fields and resorts. Whether you're hitting the slopes or wandering through charming boutiques, Chester promises a memorable vacation experience.

Shopping

In Chester, visit the Vermont Country Store for unique gifts and souvenirs just 9.7km away. My Minds Design, also 9.7km away, offers creative items. If you're up for a drive, check out the West River Farmers Market, located 17.7km away, for a vibrant local shopping experience.

Recreation

At Fox Run Golf Course, enjoy a scenic round of golf surrounded by beautiful landscapes. The Ice House Ice Skating offers a serene atmosphere for relaxation and fun on the ice. For more golfing, Stratton Mountain Golf Course provides a challenging experience with stunning outdoor views.

Adventure

At Okemo Mountain Resort, experience thrilling skiing adventures in a vibrant atmosphere, located 17.7km from Chester. The Solitude Express Ski Lift, 19.3km away, offers breathtaking views as you ascend. For a unique perspective, try Morningside Flight Park, also 19.3km from Chester, where scenic flights await you.

Nightlife

Experience a charming evening in Chester with a visit to the Weston Playhouse, just 16.1km away, for a romantic theater performance. For family fun, check out Maple Lanes, an arcade AdventureZone located 22.5km away. Don’t miss the Bellows Falls Opera House, 19.3km from Chester, for more cultural entertainment.

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

Booking tips and Expedia advantages for Chester

To save money on your trip to Chester, consider visiting during the cheaper months of April to May and November, with Tuesdays being the least expensive days for accommodation. Use Expedia to customize your travel preferences and find eco-friendly hotels at lower rates by sorting prices from lowest to highest. Additionally, combine your hotel stay, flights, and activities for package deals to maximize savings. Explore free local attractions and utilize affordable public transport options to navigate the area without breaking the bank.

  • 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: Utilize Expedia’s search tool to customize your travel preferences, such as your budget, favored location, and the type of hotel you desire. For instance, selecting the Eco-certified option will show you sustainable and eco-friendly accommodations that are currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay 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 ski and adventure enthusiasts, offering a range of outdoor activities and sports. Visitors can explore local parks, national and state parks, and historical museums, making it a perfect spot for those seeking cultural experiences and family fun. Whether you're hitting the slopes or enjoying nature, Chester has something for everyone to enjoy during their stay.

  • Vermont Museum of Mining and Minerals: Located 9.7km from Chester, this museum offers a fascinating glimpse into Vermont's geological history. With engaging exhibits focusing on minerals and mining, it provides a family-friendly atmosphere perfect for all ages.
  • Lowell Lake State Park: Just 14.5km away, this stunning state park is an outdoor lover's paradise. Experience breathtaking scenery and a variety of recreational activities, from hiking to fishing, making it ideal for adventure seekers.
  • Grafton Historical Society: Situated 9.7km from Chester, this history museum immerses visitors in the rich cultural heritage of the Grafton area. It's a delightful stop for those interested in local history and traditions.

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

To visit Chester, Vermont, you have several airport options. Lebanon Municipal Airport (LEB) is located 46.7km away, with nearby hotels like the 4-star Hanover Inn Dartmouth and the 3-star Hotel Coolidge, both offering convenient access. Rutland Southern Vermont Regional Airport (RUT) is 40.2km from Chester, with quality options including the 3.5-star Killington Mountain Lodge. For closer access, Springfield's Hartness State Airport (VSF) is only 11.3km away, featuring the 4-star Inn at Weathersfield and the 3.5-star Pointe at Castle Hill Resort. Each hotel provides various transportation services to ensure a smooth journey to and from the airports.

Frequently asked questions

Where is the best place to stay in Chester?
Located 25.2 mi (40.5 km) from the heart of Chester, Woodstock Inn & Resort is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are The Shire Woodstock 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 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 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. Kimpton Taconic Hotel by IHG and The Equinox Golf Resort & Spa 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 DaVallia Art & Accents and Bonnie's Bundles Dolls. 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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