Chester Hotels from ₹7,740

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Top 10 Chester hotels and places to stay

Fullerton Inn
2.5 star property
8.2 out of 10, Very good, (398)
"Lovely stay"
United States
Christine
The price is ₹11,333
₹12,353 total
includes taxes & fees
10 Nov - 11 Nov
Fullerton Inn
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (103)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is ₹17,618
₹19,203 total
includes taxes & fees
19 Nov - 20 Nov
Stone Hearth Inn and Eatery
Woodstock Inn & Resort
4.5 star property
9.2 out of 10, Wonderful, (541)
"Beautiful hotel!! The staff, room, and spa were fantastic!!"
United States
Marlene
The price is ₹30,660
₹37,592 total
includes taxes & fees
24 Nov - 25 Nov
Woodstock Inn & Resort
The Shire Woodstock
3.0 star property
8.8 out of 10, Excellent, (861)
"Easy check-in / check-out. Very clean property and rooms. Easily walkable location to every major point of interest in Woodstock. Highly recommend the property. "
United States
Brendan
The Shire Woodstock
The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
8.4 out of 10, Very good, (849)
"Good location; charming property "
United States
Megan
The price is ₹11,126
₹13,688 total
includes taxes & fees
2 Nov - 3 Nov
The Palmer House Resort, an Ascend Collection Hotel
The Covered Bridge Inn
2.5 star property
7.6 out of 10, Good, (1002)
"Good value for a two night stay for work "
United States
jim
The price is ₹8,001
₹8,802 total
includes taxes & fees
26 Oct - 27 Oct
The Covered Bridge Inn
Aspen At Manchester
2.5 star property
8.8 out of 10, Excellent, (597)
"Very relaxing environment. "
United States
Steve
The price is ₹9,141
₹11,020 total
includes taxes & fees
16 Nov - 17 Nov
Aspen At Manchester
Sleep Woodstock Motel
2.0 star property
9.6 out of 10, Exceptional, (538)
"Great motel with complete amenities.. beautiful surrounding especially in this fall"
United States
Giana
The price is ₹9,093
₹11,452 total
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock Motel
The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
7.6 out of 10, Good, (930)
"Great place for the price "
United States
Karen
The price is ₹11,912
₹14,414 total
includes taxes & fees
26 Oct - 27 Oct
The Black Bear Lodge at Stratton Mountain Resort
Hampton Inn and Suites Manchester
2.5 star property
9.6 out of 10, Exceptional, (1003)
"Friendly staff made everything that was good even better."
United States
Kathleen
The price is ₹11,454
₹12,600 total
includes taxes & fees
16 Nov - 17 Nov
Hampton Inn and Suites Manchester
Pointe at Castle Hill Resort
3.5 star property
8.8 out of 10, Excellent, (907)
"It was a beautiful place "
United States
Tony
The price is ₹11,314
₹12,899 total
includes taxes & fees
27 Oct - 28 Oct
Pointe at Castle Hill Resort
Best Western Plus Keene Hotel
3.0 star property
8.4 out of 10, Very good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ₹13,090
₹14,202 total
includes taxes & fees
3 Nov - 4 Nov
Best Western Plus Keene Hotel
Riverside Hotel, an Ascend Collection Hotel
2.5 star property
9.6 out of 10, Exceptional, (617)
"Loved my stay"
United States
Christine
The price is ₹13,367
₹14,503 total
includes taxes & fees
29 Oct - 30 Oct
Riverside Hotel, an Ascend Collection Hotel
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (558)
"Beautiful hotel! "
United States
sarah
The price is ₹8,874
₹14,404 total
includes taxes & fees
10 Nov - 11 Nov
The Equinox Golf Resort & Spa
Days Inn by Wyndham Keene NH
2.0 star property
7.0 out of 10, Good, (1000)
"Would stay again"
United States
Judy
The price is ₹8,886
₹9,641 total
includes taxes & fees
5 Nov - 6 Nov
Days Inn by Wyndham Keene NH
Kimpton Taconic Hotel by IHG
4.0 star property
9.4 out of 10, Exceptional, (810)
"Very nice, beautiful inn"
United States
Susan
The price is ₹14,671
₹19,521 total
includes taxes & fees
3 Nov - 4 Nov
Kimpton Taconic Hotel by IHG
Travelodge by Wyndham Brattleboro VT
2.5 star property
6.0 out of 10, (726)
"Reasonable rate for the the accomadations."
United States
David
The price is ₹7,036
₹7,740 total
includes taxes & fees
29 Oct - 30 Oct
Travelodge by Wyndham Brattleboro VT
Jackson Gore Village
3.0 star property
8.6 out of 10, Excellent, (812)
"Nice hotel and setting, wonderful customer service"
United States
Bao
The price is ₹16,340
₹19,853 total
includes taxes & fees
27 Oct - 28 Oct
Jackson Gore Village
Vantage Point Villas at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (69)
"Not enough heat"
United States
barry
The price is ₹19,803
₹24,615 total
includes taxes & fees
10 Nov - 11 Nov
Vantage Point Villas at Stratton Mountain Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
9.0 out of 10, Wonderful, (763)
"It is Good place to stay. We enjoyed our stay here."
United States
Lokesh
The price is ₹11,333
₹13,550 total
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Where to stay in Chester

Find the best Chester areas 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

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

More cheap stays in Chester

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?
Stone Hearth Inn and Eatery is ranked highly by Expedia customers. This B&B offers free breakfast and free parking. Another top choice for your trip based on reviews is Fullerton Inn. 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. The Equinox Golf Resort & Spa and Kimpton Taconic Hotel by IHG 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 Grafton Historical Society and Vermont Country Store 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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