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Chester Hotels from ₹8,024

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26 Aug - 27 Aug
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27 Aug - 28 Aug
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28 Aug - 30 Aug
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4 Sept - 6 Sept

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Kirsty
₹13,262
₹14,456 total
includes taxes & fees
31 Aug - 1 Sept
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
Olena
₹19,332
₹21,072 total
includes taxes & fees
10 Sept - 11 Sept
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
₹15,372
₹16,909 total
includes taxes & fees
2 Sept - 3 Sept
Best Western Springfield Hotel

4. The Hartness House

The Hartness House
Springfield
United States
Dan
₹16,909
₹18,600 total
includes taxes & fees
30 Aug - 31 Aug
The Hartness House

5. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
David
₹11,941
₹13,613 total
includes taxes & fees
3 Sept - 4 Sept
Pointe at Castle Hill Resort

6. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
Michael
₹15,429
₹16,818 total
includes taxes & fees
31 Aug - 1 Sept
Harvest Barn Inn

7. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Mirco
₹21,567
₹23,509 total
includes taxes & fees
6 Sept - 7 Sept
Castle Hill Resort And Spa

8. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Denis
₹12,795
₹13,883 total
includes taxes & fees
7 Sept - 8 Sept
The Common Man Inn & Restaurant

9. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
Sergio
₹10,111
₹10,970 total
includes taxes & fees
3 Sept - 4 Sept
Claremont Motor Lodge

10. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Ingrid
₹12,219
₹13,257 total
includes taxes & fees
8 Sept - 9 Sept
Keene Elm City Hotel, an Ascend Collection Hotel

11. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
₹8,037
₹8,921 total
includes taxes & fees
3 Sept - 4 Sept
The Upper Pass Lodge at Magic Mountain

12. The Putney Inn

The Putney Inn
Putney
United States
JANE
₹10,390
₹11,429 total
includes taxes & fees
1 Sept - 2 Sept
The Putney Inn

13. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Gene
₹13,308
₹16,086 total
includes taxes & fees
27 Aug - 28 Aug
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

14. Royal Inn Claremont

Royal Inn Claremont
Claremont
United States
Eva
₹10,305
₹11,180 total
includes taxes & fees
30 Aug - 31 Aug
Royal Inn Claremont

15. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
Kristina
₹13,926
₹15,319 total
includes taxes & fees
1 Sept - 2 Sept
Main and Mountain Bar & Motel

16. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Cynthia
₹18,548
₹22,535 total
includes taxes & fees
31 Aug - 1 Sept
Jackson Gore Village, A Vail Resorts Property

17. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Morgan
₹11,273
₹12,400 total
includes taxes & fees
6 Sept - 7 Sept
Comfort Inn & Suites Brattleboro I-91

18. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
₹14,074
₹15,482 total
includes taxes & fees
27 Aug - 28 Aug
Blue Gentian Lodge at Magic Mountain

19. Bromley View Inn

Bromley View Inn
Bondville
Canada
William
₹7,295
₹8,024 total
includes taxes & fees
3 Sept - 4 Sept
Bromley View Inn

20. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
United States
Tatiana
₹14,787
₹16,266 total
includes taxes & fees
8 Sept - 9 Sept
Hampton Inn and Suites Manchester
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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, 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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Very nice hotel off main road in and out of Manchester. Great outdoor porches to sit and relax. Free beverage coupons at social hour with free popcorn and pretzels. Staff friendly. Rooms very nice, spacious and beds very comfortable. Room temps were great. Free coffee in lobby area, free easy parking. $30 resort fee we didn't use any of the amenities. Walkable to shops and other nice restaurants."
mary ellen 1-night trip
Posted 1 hour ago
Kimpton Taconic Hotel by IHG
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"great time"
Edward 2-night trip
Posted 2 hours ago
Hampton Inn and Suites Manchester
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"Clean room breakfast was good"
Lori 1-night trip
Posted 5 hours ago
Best Western Plus Keene Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"It was good!"
Ingrid 4-night trip
Posted 18 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
The Shire Woodstock

The Shire Woodstock

8/10 Good
"It was a nice and cozy place to stay and experience Woodstock VT."
Clayton 2-night trip
Posted 2 days ago
The Shire Woodstock
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"👍"
Chris 1-night trip
Posted 2 days ago
The Palmer House Resort, an Ascend Collection Hotel
Colonial Motel

Colonial Motel

8/10 Good
"X"
Steven 1-night trip
Posted 2 days ago
Colonial Motel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."
Chris 2-night trip
Posted 4 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Staff were extremely friendly. The whole place was clean. Hit tub was really a whirlpool..movement but no bubbles. So nice and warm though. Great stay!!"
Deborah 2-night trip
Posted 5 days ago
Hampton Inn Brattleboro

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
₹9,246
₹10,032 total
16 Sept - 17 Sept
includes taxes & fees
7/10 Good! (1,006 reviews)
Days Inn by Wyndham Keene NH
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
₹10,307
₹11,337 total
27 Aug - 28 Aug
includes taxes & fees
Latchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
₹10,823
₹11,905 total
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
₹11,273
₹12,400 total
6 Sept - 7 Sept
includes taxes & fees
8.6/10 Excellent! (849 reviews)
Comfort Inn & Suites Brattleboro I-91
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
₹12,219
₹13,257 total
8 Sept - 9 Sept
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
₹14,787
₹16,266 total
8 Sept - 9 Sept
includes taxes & fees
9.6/10 Exceptional! (1,001 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?
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 traveller data. Other good choices for your stay in the area are Kimpton Taconic Hotel by IHG and Holiday Inn Club Vacations Mount Ascutney Resort 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 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. Kimpton Taconic Hotel by IHG and Keene Elm City Hotel, an Ascend Collection Hotel 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 62 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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