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27 Sep - 28 Sep
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28 Sep - 29 Sep
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2 Oct - 4 Oct
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9 Oct - 11 Oct

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Lisa
AED 584
AED 637 total
includes taxes & fees
18 Oct - 19 Oct
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
John
AED 953
AED 1,039 total
includes taxes & fees
30 Sep - 1 Oct
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
AED 658
AED 724 total
includes taxes & fees
18 Oct - 19 Oct
Best Western Springfield Hotel

4. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
AED 621
AED 708 total
includes taxes & fees
18 Oct - 19 Oct
Pointe at Castle Hill Resort

5. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
AED 855
AED 1,067 total
includes taxes & fees
30 Sep - 1 Oct
The Inn at Weathersfield

6. The Hartness House

The Hartness House
Springfield
United States
Gregory
AED 759
AED 835 total
includes taxes & fees
25 Oct - 26 Oct
The Hartness House

7. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
Michael
AED 658
AED 717 total
includes taxes & fees
26 Oct - 27 Oct
Harvest Barn Inn

8. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
AED 621
AED 683 total
includes taxes & fees
29 Sep - 30 Sep
Blue Gentian Lodge at Magic Mountain

9. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
AED 314
AED 359 total
includes taxes & fees
30 Sep - 1 Oct
The Upper Pass Lodge at Magic Mountain

10. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
United States
Raedene
AED 754
AED 822 total
includes taxes & fees
29 Sep - 30 Sep
COHO Inn & Motor Lodge

11. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Daniel
AED 607
AED 737 total
includes taxes & fees
30 Sep - 1 Oct
Jackson Gore Village, A Vail Resorts Property

12. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Donnie
AED 674
AED 732 total
includes taxes & fees
18 Oct - 19 Oct
The Common Man Inn & Restaurant

13. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
Bromley Mountain
United States
Mary
AED 531
AED 585 total
includes taxes & fees
30 Sep - 1 Oct
Sun Lodge near Manchester VT, Ascend Collection Hotel

14. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
Patricia
AED 932
AED 1,061 total
includes taxes & fees
29 Sep - 30 Sep
Main and Mountain Bar & Motel

15. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
AED 820
AED 894 total
includes taxes & fees
20 Oct - 21 Oct
Castle Hill Resort And Spa

16. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
Jerri
AED 392
AED 426 total
includes taxes & fees
29 Oct - 30 Oct
Claremont Motor Lodge

17. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
United States
DENNIS
AED 490
AED 593 total
includes taxes & fees
30 Sep - 1 Oct
The Black Bear Lodge at Stratton Mountain Resort

18. Bromley View Inn

Bromley View Inn
Bondville
Canada
William
AED 285
AED 313 total
includes taxes & fees
29 Sep - 30 Sep
Bromley View Inn

19. Royal Inn Claremont

Royal Inn Claremont
Claremont
United States
Eva
AED 446
AED 484 total
includes taxes & fees
29 Sep - 30 Sep
Royal Inn Claremont

20. The Putney Inn

The Putney Inn
Putney
United States
JANE
AED 309
AED 340 total
includes taxes & fees
25 Oct - 26 Oct
The Putney Inn
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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

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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"We will be back. Wonderful staff and great location."
Melissa 1-night trip
Posted 3 hours ago
Hampton Inn and Suites Manchester
Aspen At Manchester

Aspen At Manchester

8/10 Good
"Nice clean place. Easy check in. Good location"
Robert 1-night trip
Posted 3 hours ago
Aspen At Manchester
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"We were only there one day but we had a great time"
Daniel 1-night trip
Posted 5 hours ago
Jackson Gore Village, A Vail Resorts Property
The Jackson

The Jackson

10/10 Excellent
"Garden and grounds out back were very nice. Restaurant provided great dinner and breakfast."
Rick 2-night trip
Posted 7 hours ago
The Jackson
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Our 2nd floor room with balcony was beautiful, large, clean, and with excellent amenities, also looking over the waterfront. The bed was very comfortable. We enjoyed breakfast each morning very much. Our server is friendly and helpful. We were able to get close-in parking. Desk staff were also friendly. We visited Kelleyway Gardens and spoke with Clement. She is a delightful young lady who offered good information about the area. This was our second stay and we will visit again."
Darrell 2-night trip
Posted 8 hours ago
Woodstock Inn & Resort
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"What I like is the room was well stocked, very clean and the staff is very helpful. What I did not like is the parking is very inconvenient and is quite a walk which is never fun in bad weather. They need more luggage carts. It looked like they have about 5 or 6 for about a 200 room hotel. There was only one place on the property to get breakfast in the morning. There is a stove and refrigerator in the room. I had no idea before hand those would be available!"
Richard 2-night trip
Posted 9 hours ago
Grand Summit Resort, A Vail Resorts Property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

8/10 Good
"This location has everything all in one, Bed&Breakfast, restaurant and location. The staff is very engaging and friendly. The food was very good, but the only disappointment was dealing with little flies or gnats in the dining room. Without the pests this would have been a perfect place. The locals appear to love this place for dining and takeout."
Richard 1-night trip
Posted 10 hours ago
Stone Hearth Inn and Eatery
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"all was wonderful and well orchestrated"
Peter 3-night trip
Posted 12 hours ago
Kimpton Taconic Hotel by IHG
The Manchester View

The Manchester View

10/10 Excellent
"Great value super clean I will be back"
Sarah 1-night trip
Posted 13 hours ago
The Manchester View

More cheap stays in Chester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
AED 309
AED 340 total
25 Oct - 26 Oct
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
The Putney Inn
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
AED 394
AED 434 total
26 Oct - 27 Oct
includes taxes & fees
9.4/10 Exceptional! (908 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
AED 459
AED 498 total
27 Oct - 28 Oct
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
AED 438
AED 522 total
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (695 reviews)
Aspen At Manchester
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
AED 491
AED 540 total
29 Sep - 30 Sep
includes taxes & fees
8.6/10 Excellent! (990 reviews)
Latchis Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
AED 569
AED 626 total
26 Oct - 27 Oct
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
Hampton Inn and Suites Manchester

Hotels in Chester with star-rating

Find out more about Chester

Top reasons to visit Chester

  • Outstanding Skiing Opportunities: Chester is a haven for ski enthusiasts with various local ski resorts offering thrilling winter sports.
  • Charming Local Shops: The town features quirky boutiques that provide a unique shopping experience, adding to Chester's charm.
  • Beautiful Parks and Nature: Visitors can explore stunning parks and state parks, perfect for outdoor adventures and family outings.
  • Rich Historical Sites: Chester boasts historical museums and sites, enriching your understanding of the local culture.
  • Diverse Lodging Options: From cozy B&Bs to unique agritourism stays, Chester offers accommodations for every type of traveler.

Find great hotels near Chester

Experience the charm of Chester, Vermont, with a variety of lodging options that cater to every traveler. From cozy bed & breakfasts to unique agritourism properties, you'll find accommodations perfect for family adventures or pet-friendly getaways. Explore Chester's hotels and inns, read reviews, and discover the perfect hotel rooms to make your stay memorable in this picturesque destination.

  • Best Western Springfield Hotel: Nestled 12.9km from Chester, Best Western Springfield Hotel is a welcoming retreat for pet owners and their furry friends. This hotel prides itself on providing a pet-friendly atmosphere, ensuring that your pets are treated with care. With amenities such as designated dog areas and a flexible pet policy, it caters to travelers looking for a comfortable stopover. The hotel features cozy accommodations, complimentary breakfast, and a fitness center, making it an ideal choice for families and those seeking a convenient base to explore the surrounding area.
  • Pointe at Castle Hill Resort: Located 14.5km from Chester, Pointe at Castle Hill Resort offers a luxurious escape for adventure enthusiasts and business travelers alike. This 3.5-star hotel features an array of exciting activities such as rafting, hiking, and skiing nearby, ensuring an action-packed stay. Guests can unwind at the full-service spa, which includes rejuvenating body wraps and facial treatments, or take a dip in the pool and hot tub. The resort's elegant accommodations and business facilities make it a perfect blend of relaxation and productivity, appealing to those who seek both adventure and comfort.
  • Jackson Gore Village: Situated 20.9km from Chester, Jackson Gore Village is an excellent choice for those who love skiing and golfing. This 3-star hotel offers direct access to ski lifts and shuttles, making it easy for guests to hit the slopes. With on-site amenities for snow tubing and snowshoeing, adventure is right at your doorstep. Golf enthusiasts will appreciate the nearby golfing opportunities, while comfortable accommodations provide a cozy retreat after a day of outdoor activities. Jackson Gore Village is perfect for families and groups looking for a fun-filled getaway.

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 for its friendly atmosphere and historical sites, or head to nearby areas for skiing and outdoor sports. With various recreational opportunities, you can enjoy both budget-friendly and luxurious experiences. Whether you're seeking thrilling activities or a peaceful retreat, Chester has something for every traveler to enjoy.

  • Ludlow: Nestled 17.7km from Chester, Ludlow is a charming city known for its vibrant ski culture. Visitors flock here for thrilling winter sports and adventure activities, making it a popular destination from December to February. The ski fields and resorts are prime spots for both novices and seasoned skiers. In addition to winter sports, Ludlow's stunning natural landscapes, including lakes and mountains, provide the perfect backdrop for outdoor enthusiasts year-round.
  • Springfield: Located just 9.7km from Chester, Springfield offers a diverse travel experience with a mix of adventure and nature. The city attracts visitors throughout the year, with peak seasons occurring in February, July, and September. Known for its ski resorts and outdoor activities, Springfield is a hub for sports lovers. Nearby attractions, including lakes and national state parks, invite exploration and relaxation, making it a well-rounded destination for all types of travelers.
  • Grafton: Situated 9.7km away from Chester, Grafton is a picturesque city that draws visitors for its outdoor adventures and stunning scenery. With peak travel times in July and September to October, Grafton is perfect for those seeking both adrenaline-pumping activities and serene landscapes. The nearby ski fields and resorts cater to winter sports enthusiasts, while the surrounding valleys and mountains offer breathtaking views and trails for hiking and exploring in the warmer months.

Things to do near Chester

Chester, Vermont, is a perfect destination for ski enthusiasts and adventure seekers. Visitors can enjoy a variety of skiing options at local ski resorts, along with numerous outdoor activities. Beyond the slopes, the town features quirky shops that add a unique charm to your experience. Whether you're hitting the trails or exploring the local boutiques, Chester offers a delightful mix of adventure and leisure for every traveler.

Shopping

In Chester, you can shop at the Vermont Country Store and My Minds Design, both located 9.7km away. If you're up for a drive, visit the West River Farmers Market, 17.7km away, for a vibrant local market experience with fresh produce and unique crafts.

Recreation

Fox Run Golf Course offers a picturesque setting for golf enthusiasts, featuring lush greens and outdoor activities just 19.3km from Chester. For a more relaxed atmosphere, visit The Ice House Ice Skating, located 20.9km away, where you can enjoy skating in a tranquil environment. Stratton Mountain Golf Course, also 20.9km away, provides more outdoor sports opportunities amidst stunning views.

Adventure

At Okemo Mountain Resort, 17.7km from Chester, experience thrilling skiing and snowboarding on diverse trails. The Solitude Express Ski Lift, located 19.3km away, offers breathtaking views and easy access to adventure slopes. For an unforgettable experience, soar through the skies at Morningside Flight Park, also 19.3km from Chester.

Nightlife

Experience a vibrant nightlife in Chester with a visit to the Weston Playhouse for captivating performances, or enjoy family fun at Maple Lanes arcade. For a dose of culture, catch a show at the Bellows Falls Opera House, where romance and entertainment blend seamlessly.

*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, Vermont, consider visiting during the off-peak months of April to May or November, when accommodation prices are lower. Tuesdays are the cheapest days to stay, while Fridays tend to be more expensive. Use Expedia to filter for budget-friendly hotels and combine your bookings for flights and activities to secure package deals. Additionally, explore free local attractions and utilize public transport for affordable travel around the area, ensuring a memorable yet cost-effective vacation.

  • 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 preferences, such as budget, desired location, and the type of hotel you’re looking for. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservations 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 enthusiasts and adventure seekers, offering a variety of outdoor activities and cultural experiences. Visitors can explore beautiful parks, historical museums, and state parks that cater to families and travelers looking for enriching experiences. Whether you're in the mood for sports or simply soaking in the local history, Chester provides a unique blend of nature and culture for an unforgettable vacation.

  • Vermont Museum of Mining and Minerals: Located 9.7km from Chester, this museum offers a fascinating glimpse into Vermont's mining history. Families can explore interactive exhibits and discover the rich geological resources of the region, making it both educational and entertaining.
  • Lowell Lake State Park: Just 14.5km away, this state park is a haven for outdoor enthusiasts. With its stunning scenery, visitors can enjoy hiking, fishing, and picnicking amidst nature’s beauty, providing a perfect backdrop for adventure seekers.
  • Grafton Historical Society: Situated 9.7km from Chester, this historical society presents a deep dive into local history. Visitors can appreciate the cultural heritage of the area through exhibits and artifacts, enriching their understanding of Grafton's past.

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

When visiting Chester, Vermont, there are several nearby airports to consider. Lebanon Municipal Airport (LEB) is located 46.7km away, with nearby accommodations like the 4-star Hanover Inn Dartmouth, 8.0km from the airport, and the 3-star Hotel Coolidge, 3.2km away. Rutland Southern Vermont Regional Airport (RUT) is 28.0km away, featuring hotels such as the 3.5-star Killington Mountain Lodge, 17.7km from the airport, and the Snowed Inn, also 17.7km away. The closest option is Hartness State Airport (VSF) in Springfield, just 11.3km away, with the 4-star Inn at Weathersfield located 1.6km from the airport, offering convenient access to Chester.

Frequently asked questions

What's the top vacation rental that Chester has to offer?
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: Visitors like this Chester vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all 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 hotel for a family vacation to Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a guesthouse with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families. Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are also fun for kids of all ages. Find more child-friendly accommodations in Chester.
What's the best accommodation for a romantic vacation in Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favorite guesthouse for couples, and features free WiFi and a garden. See all romantic hotels in Chester.
What's the best pet-friendly accommodation in Chester?
Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains is a top pet-friendly option for your stay. Motel in the Meadow is another good choice for you and your pet. 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. The Manchester View and Pointe at Castle Hill Resort 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 66 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. 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.