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Oct 13 - Oct 14
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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
kris
NT$4,118
NT$4,489 total
includes taxes & fees
Nov 10 - Nov 11
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
John
NT$7,458
NT$8,129 total
includes taxes & fees
Nov 13 - Nov 14
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Dzmitry
NT$4,856
NT$5,342 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Springfield Hotel

4. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
NT$4,865
NT$5,546 total
includes taxes & fees
Oct 28 - Oct 29
Pointe at Castle Hill Resort

5. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Dorrie
NT$7,237
NT$9,064 total
includes taxes & fees
Nov 5 - Nov 6
The Inn at Weathersfield

6. The Hartness House

The Hartness House
Springfield
United States
Zhenchun
NT$6,438
NT$7,082 total
includes taxes & fees
Nov 10 - Nov 11
The Hartness House

7. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
United States
Rosemary
NT$4,857
NT$5,343 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn and Suites Manchester

8. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
gail
NT$4,857
NT$5,294 total
includes taxes & fees
Nov 2 - Nov 3
Harvest Barn Inn

9. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Jessica
NT$5,896
NT$7,163 total
includes taxes & fees
Nov 11 - Nov 12
Jackson Gore Village, A Vail Resorts Property

10. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Timothy
NT$4,725
NT$5,198 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Hotel & Suites Brattleboro by IHG

11. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
Canada
Bruce
NT$4,137
NT$4,489 total
includes taxes & fees
Nov 1 - Nov 2
The Common Man Inn & Restaurant

12. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
NT$3,057
NT$3,500 total
includes taxes & fees
Oct 15 - Oct 16
The Upper Pass Lodge at Magic Mountain

13. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
NT$8,591
NT$9,364 total
includes taxes & fees
Oct 26 - Oct 27
Castle Hill Resort And Spa

14. The Manchester View

The Manchester View
Manchester Center
United States
Jan
NT$3,233
NT$3,556 total
includes taxes & fees
Nov 3 - Nov 4
The Manchester View

15. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
NT$3,532
NT$3,885 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Brattleboro I-91

16. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
NT$4,757
NT$5,232 total
includes taxes & fees
Nov 3 - Nov 4
Blue Gentian Lodge at Magic Mountain

17. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
David
NT$6,447
NT$7,092 total
includes taxes & fees
Oct 21 - Oct 22
Main and Mountain Bar & Motel

18. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
Bromley Mountain
United States
Lynn
NT$3,805
NT$4,186 total
includes taxes & fees
Nov 13 - Nov 14
Sun Lodge near Manchester VT, Ascend Collection Hotel

19. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
United States
Joseph
NT$4,757
NT$5,756 total
includes taxes & fees
Oct 14 - Oct 15
The Black Bear Lodge at Stratton Mountain Resort

20. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Faith
NT$3,690
NT$4,059 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Brattleboro
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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

Bonnie's Bundles Dolls

7.6/10 (4 reviews)
This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.
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DaVallia Art & Accents

10.0/10 (2 reviews)
This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.
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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
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"I can’t say enough about how enjoyable it was! Will be back!"
Allison 3-night trip
Posted 6 hours ago
Jackson Gore Village, A Vail Resorts Property
Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"everything was amazing! Beautiful hotel, room was huge and beds sooo comfortable! Everyone was super friendly and accomodating. Cant wait to go back!"
Hope I 2-night trip
Posted 9 hours ago
Aspen At Manchester
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Perfect for our one night stay. Rooms were clean. Staff were friendly and helpful. Restaurants within walkable distance."
Sarah 1-night trip
Posted 11 hours ago
Hampton Inn and Suites Manchester
The Manchester View

The Manchester View

8/10 Good
"Beautiful room, very clean and new. It was very bare in the room though. Breakfast from 8-10 and we went at 9:40, it was wiped out with nobody refilling so make sure you go early. Next day we went early and it was delicious! Hot tub was amazing which we used both nights. Overall, the views are gorgeous and highly recommend this hotel."
Marybeth 2-night trip
Posted 14 hours ago
The Manchester View
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

8/10 Good
"Hard to find the hot tub. Strange to not have staff there."
Ginger 1-night trip
Posted 1 day ago
Hideaway Inn Mt. Snow
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."
Teresa D 1-night trip
Posted 1 day ago
Best Western Plus Keene Hotel
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Room was spacious and very clean upon arrival. Staff was also very attentive and took care all our needs."
Marlene 3-night trip
Posted 2 days ago
Woodstock Inn & Resort
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"It's a great place to stay! I've been there several times in different seasons. Off-season or leaf peeper season the free breakfast is a lot less than the free breakfast during ski season. During ski season AKA winter, eggs, waffles, pancakes etc however during other seasons they only offer cold cereal, milk bagels toast and juice and coffee of course. Other than that it's a fantastic place and they're dog friendly"
Bridget 1-night trip
Posted 2 days ago
The Black Bear Lodge at Stratton Mountain Resort
Colonial Motel

Colonial Motel

8/10 Good
"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."
Leonard 3-night trip
Posted 4 days ago
Colonial Motel

More cheap stays in Chester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
NT$2,686
NT$2,955 total
Nov 8 - Nov 9
includes taxes & fees
The Putney Inn
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
NT$3,233
NT$3,556 total
Nov 3 - Nov 4
includes taxes & fees
9.4/10 Exceptional! (927 reviews)
The Manchester View
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
NT$3,799
NT$4,122 total
Nov 11 - Nov 12
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
NT$3,949
NT$4,695 total
Nov 9 - Nov 10
includes taxes & fees
8.8/10 Excellent! (702 reviews)
Aspen At Manchester
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
NT$4,526
NT$4,978 total
Nov 1 - Nov 2
includes taxes & fees
Latchis Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
NT$4,857
NT$5,343 total
Nov 8 - Nov 9
includes taxes & fees
9.6/10 Exceptional! (1,009 reviews)
Hampton Inn and Suites Manchester

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?
Based on our traveler data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. Stone Hearth Inn and Eatery is another good choice for your stay. 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. Aspen At Manchester and The Manchester View 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. 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. You'll also find Vermont Country Store and Lowell Lake State Park 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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