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10 Oct - 11 Oct
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11 Oct - 12 Oct
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16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
kris
₹12,479
₹13,602 total
includes taxes & fees
9 Nov - 10 Nov
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
John
₹25,099
₹27,358 total
includes taxes & fees
14 Oct - 15 Oct
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
₹14,714
₹16,186 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Springfield Hotel

4. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
₹13,911
₹15,859 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
Dorrie
₹20,615
₹26,030 total
includes taxes & fees
4 Nov - 5 Nov
The Inn at Weathersfield

6. The Hartness House

The Hartness House
Springfield
United States
Elizabeth
₹19,272
₹21,199 total
includes taxes & fees
8 Nov - 9 Nov
The Hartness House

7. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
gail
₹13,099
₹14,278 total
includes taxes & fees
1 Nov - 2 Nov
Harvest Barn Inn

8. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Jessica
₹17,439
₹21,187 total
includes taxes & fees
26 Oct - 27 Oct
Jackson Gore Village, A Vail Resorts Property

9. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
₹8,938
₹10,234 total
includes taxes & fees
12 Oct - 13 Oct
The Upper Pass Lodge at Magic Mountain

10. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
United States
Rosemary
₹14,718
₹16,190 total
includes taxes & fees
5 Nov - 6 Nov
Hampton Inn and Suites Manchester

11. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
₹20,825
₹22,699 total
includes taxes & fees
19 Oct - 20 Oct
Castle Hill Resort And Spa

12. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
Canada
Bruce
₹12,537
₹13,603 total
includes taxes & fees
1 Nov - 2 Nov
The Common Man Inn & Restaurant

13. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Timothy
₹13,446
₹14,791 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG

14. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
Patricia
₹19,537
₹21,491 total
includes taxes & fees
19 Oct - 20 Oct
Main and Mountain Bar & Motel

15. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
₹14,414
₹15,855 total
includes taxes & fees
3 Nov - 4 Nov
Blue Gentian Lodge at Magic Mountain

16. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
Caroline
₹16,774
₹18,200 total
includes taxes & fees
25 Oct - 26 Oct
Fairfield Inn & Suites by Marriott Keene Downtown

17. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
United States
Raedene
₹19,850
₹21,637 total
includes taxes & fees
15 Oct - 16 Oct
COHO Inn & Motor Lodge

18. The Manchester View

The Manchester View
Manchester Center
United States
Jan
₹9,794
₹10,774 total
includes taxes & fees
3 Nov - 4 Nov
The Manchester View

19. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
₹10,702
₹11,772 total
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Brattleboro I-91

20. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
Jeffrey
₹10,680
₹11,587 total
includes taxes & fees
18 Oct - 19 Oct
Claremont Motor Lodge
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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

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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

8/10 Good
"Nice facility. Clean and convenient."
Peter 2-night trip
Posted 1 hour ago
Pointe at Castle Hill Resort
Latchis Hotel

Latchis Hotel

8/10 Good
"Love the old-fashioned, art, deco, charm, and having the turntables and old records in the room… And having the movie theater attached…. I think this is a work in progress. The carpeting is really old in the rooms and there were laundry bags left out for the laundry to pick up all day… And because they don’t staff from 10 PM to 9 AM on a Saturday I had to literally fill the water jug for the Keurig coffee from my tub… Could you not. But the staff was great and it’s a cool looking old hotel… The windows need to be clean so I could actually see the mountains out of my room… And be able to close the outside windows. If you want old World charm give it a try… But I’m hoping or not for private he has taken this over. I’ll put some more cash into it because it’s worth it."
Jayne 2-night trip
Posted 4 hours ago
Latchis Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Great location and staff is AWESOME! Thanks for another pleasant stay!!"
Carey 1-night trip
Posted 17 hours ago
Hampton Inn and Suites Manchester
The Manchester View

The Manchester View

10/10 Excellent
"We loved this property, our view opened up to magnificent Mountain View, if you are there during lead peeping season you know that makes a difference. We enjoyed the hot tub at night and the fireplace . Kind staff, they left cookies and bowls for our dog, breakfast was delicious, the variety of baked goods was perfect and the Vermont coffee provided brought up to a higher level I can’t wait to go back for a longer stay"
Cathya 1-night trip
Posted 19 hours ago
The Manchester View
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good
"Raymond was great at check in"
Kevin 1-night trip
Posted 23 hours ago
The Palmer House Resort, an Ascend Collection Hotel
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

10/10 Excellent
"This place was great! Super cute and clean"
Kailee 1-night trip
Posted 2 days ago
Hideaway Inn Mt. Snow
Fullerton Inn

Fullerton Inn

10/10 Excellent
"Clean rooms"
Theresa 2-night trip
Posted 2 days ago
Fullerton Inn
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 2 days ago
Colonial Motel
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good
"Nice hotel. Dated, but nice. Internet speed and connectivity is terrible. Good launching point for the Stowe area attractions to allow access off of back routes to avoid traffic. No breakfast."
Steven 1-night trip
Posted 2 days ago
The Black Bear Lodge at Stratton Mountain Resort

More cheap stays in Chester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
₹8,140
₹8,954 total
1 Nov - 2 Nov
includes taxes & fees
The Putney Inn
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
₹9,794
₹10,774 total
3 Nov - 4 Nov
includes taxes & fees
9.4/10 Exceptional! (925 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
₹11,511
₹12,490 total
2 Nov - 3 Nov
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
₹11,966
₹14,226 total
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (699 reviews)
Aspen At Manchester
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
₹13,712
₹15,083 total
1 Nov - 2 Nov
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
Latchis Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
₹14,718
₹16,190 total
5 Nov - 6 Nov
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
Hampton Inn and Suites Manchester

Find out more about Chester

Top reasons to visit Chester

  • Thrilling Outdoor Activities: Chester is a haven for skiing and adventure enthusiasts, offering exhilarating sports experiences amidst stunning landscapes.
  • Charming Historical Architecture: Stroll through central Chester to admire its quaint streets featuring delightful historical buildings.
  • Diverse Accommodation Options: From cosy bed and breakfasts to unique agritourism properties, Chester caters to various traveller needs.
  • Family-Friendly Attractions: Enjoy a range of parks and history museums, making Chester perfect for families and culture lovers alike.
  • Natural Beauty: The picturesque ski fields and surrounding nature provide an idyllic backdrop for relaxation and exploration.

Find great hotels near Chester

Discover the charm of Chester, Vermont, where a variety of accommodation options await to cater to every traveller's needs. From delightful bed and breakfasts to unique agritourism properties, you’ll find family-friendly and pet-friendly lodgings that enhance your adventure. Explore the local offerings and enjoy a memorable stay in this picturesque town, with access to amenities that ensure a comfortable experience for all.

  • Best Western Springfield Hotel: Nestled 12.9km from Chester, the Best Western Springfield Hotel offers a warm, pet-friendly environment, making it ideal for travellers who wish to bring their furry friends along. With amenities such as a waived fee for service animals and a pet policy that welcomes dogs, this hotel ensures a comfortable stay for both you and your pets. Enjoy a soothing atmosphere and convenient access to local attractions while indulging in a homely experience.
  • Pointe at Castle Hill Resort: Located 14.5km from Chester, the Pointe at Castle Hill Resort is a 3.5-star retreat that perfectly blends business and leisure. Designed for the adventurous spirit, this resort features multiple meeting rooms and a fully accessible business centre for corporate guests. For those seeking recreation, the hotel offers a variety of adventure sports nearby, including horse riding and ziplining. Unwind in the full-service spa or enjoy a dip in the indoor pool after a day of exploration, making this location an excellent choice for a balanced getaway.
  • Jackson Gore Village: Situated 20.9km from Chester, the Jackson Gore Village is a delightful 3-star accommodation tailored for family fun and golf enthusiasts. Engage in golf activities on-site while the little ones enjoy the mini-golf, sledding, and arcade games available. With a variety of adventure sports, including on-site skiing and snow tubing, this resort promises a thrilling experience for the entire family. The playground and shared facilities ensure that children have a fantastic time, making it an ideal spot for a memorable family holiday.

Where to stay near Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation, perfect for any traveller. Explore the charming streets of central Chester, where historical architecture meets a friendly atmosphere. Enjoy skiing and outdoor sports nearby, or unwind in a beautiful bedroom home. With options for both budget and luxury stays, Chester is an ideal base for discovering the surrounding regions, making it a memorable getaway for all types of visitors.

  • Ludlow: Nestled 17.7km from Chester, Ludlow is a charming city that draws visitors year-round, particularly peaking between December and February when the slopes are alive with skiers. The town is known for its adventurous spirit, offering a wealth of outdoor activities, particularly skiing at its renowned ski resorts. Surrounded by stunning natural landscapes, Ludlow boasts picturesque lakes, majestic mountains, and serene valleys that provide the perfect backdrop for your holiday. Whether you’re hitting the slopes or enjoying the scenic beauty, Ludlow promises a memorable experience.
  • Springfield: Located a mere 9.7km from Chester, Springfield is a vibrant city that welcomes tourists throughout the year, with peaks during February, July, and September. Known for its adventurous ethos, Springfield is the place for skiing enthusiasts and outdoor adventurers alike. With easy access to ski fields and resorts, it’s an ideal base for those looking to embrace the winter sports culture. Nearby, you’ll find breathtaking lakes, stunning mountains, and the expansive national state park, offering an abundance of recreational opportunities for nature lovers.
  • Grafton: Just 9.7km from Chester, Grafton is a scenic city that captivates visitors with its natural beauty and outdoor appeal. The city sees a steady stream of travellers, particularly in July and the autumn months of September to October. Grafton is perfect for those seeking adventure, especially skiing, as it features excellent ski resorts and trails. The surrounding area is adorned with serene lakes, lovely valleys, and impressive mountains, making it a picturesque retreat for outdoor enthusiasts and those looking to unwind in nature.

Things to do near Chester

Chester, Vermont, is an ideal destination for skiing and adventure enthusiasts. Visitors can enjoy a variety of activities, including skiing at local resorts and exploring the picturesque ski fields. Whether you're an experienced skier or a beginner, Chester offers the perfect setting for an exhilarating sports vacation amidst its stunning natural landscapes.

Shopping

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

Recreation

Crown Point Golf Course, located 12.9km from Chester, offers a vibrant outdoor experience with its scenic fairways and engaging sports atmosphere. Similarly, Fox Run Golf Course, 19.3km away, invites you to enjoy the beauty of nature while honing your golfing skills. For a relaxing retreat, visit The Ice House Ice Skating, situated 20.9km from Chester, where you can unwind in a soothing environment.

Adventure

Okemo Mountain Resort, located 17.7km from Chester, offers exhilarating skiing experiences with vibrant sports vibes. For a different thrill, Morningside Flight Park, 19.3km away, provides breathtaking scenic flights amidst stunning landscapes. Additionally, the Solitude Express Ski Lift, also 19.3km from Chester, delivers adventurous ski experiences.

Nightlife

Experience the charm of Chester's nightlife with a visit to the Weston Playhouse, a delightful theatre 16.1km away, perfect for culture and romance. For adventure, try the Timber Ripper Mountain Coaster, 20.9km from Chester, or enjoy fun at Maple Lanes, an arcade adventure zone 22.5km away.

*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 during your visit to Chester, plan your trip between April to May or November for lower accommodation prices. Tuesdays are the cheapest days to stay, while Fridays are the most expensive. Use Expedia's search tool to find budget-friendly hotels, and consider bundling your flights and activities for additional savings. Explore the area on foot or utilise public transport to keep costs down, and take advantage of free outdoor activities to enhance your experience 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: Utilise Expedia’s search tool to refine your options based on your budget, preferred location, and the type of accommodation you desire. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Chester hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Chester

Chester, Vermont, offers an ideal getaway for those seeking skiing, adventure, and sports. Visitors can explore a variety of attractions, including parks, the national state park, and history museums. With options for outdoor enthusiasts, culture lovers, and families alike, Chester ensures a delightful and enriching experience for every traveller, making it a perfect destination for your holiday.

  • DaVallia Art & Accents: Immerse yourself in the vibrant culture of Chester at this delightful gallery, showcasing a variety of local and regional artwork. The unique pieces on display reflect the artistic spirit of Vermont, making it a perfect spot for art enthusiasts.
  • Lowell Lake State Park: Just 14.5km from Chester, this stunning national park offers an abundance of outdoor adventure. Enjoy hiking, fishing, and picnicking amidst breathtaking scenery, with tranquil lake views and lush forests that invite exploration.
  • Bonnie's Bundles Dolls: Located in Chester, this charming attraction is a whimsical experience filled with handmade dolls. The romantic atmosphere and intricate craftsmanship are sure to captivate visitors of all ages, making it a delightful stop for families.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, 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

Chester, Vermont, is conveniently located near several airports. Lebanon Municipal Airport (LEB) is approximately 46.7km away, with nearby accommodations like the 4-star Hanover Inn Dartmouth and the 3-star Hotel Coolidge, both providing easy access to the airport. Rutland Southern Vermont Regional Airport (RUT) is situated about 40.2km from Chester, offering hotel options such as Killington Grand Hotel and Snowed Inn, both 10 to 17.7km away. Additionally, Springfield Hartness State Airport (VSF) is a mere 11.3km from Chester, with the 4-star Inn at Weathersfield just 1.6km away, ensuring quick transport for travellers.

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. Stone Hearth Inn and Eatery is another good choice for your visit. 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. Aspen At Manchester and The Manchester View 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 67 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. 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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