Chester Hotels from ₹8,241

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Our top choices for Chester hotels

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
This charming B&B offers free WiFi and parking with a daily buffet breakfast. Outdoor enthusiasts will love the nearby hiking trails and mountain biking, while popular attractions like Bonnie's Bundles Dolls are just minutes away.

"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is ₹18,287
₹19,933 total
includes taxes & fees
23 Dec - 24 Dec
Stone Hearth Inn and Eatery

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (403)
Experience small-town allure at this Chester inn with free breakfast, WiFi, and parking. Grab a drink at the bar, dine at the restaurant, and explore nearby DaVallia Art and Bonnie's Bundles Dolls. Guests rave about the clean rooms and helpful staff.

"Lovely stay"
United States
Christine
The price is ₹11,519
₹12,556 total
includes taxes & fees
11 Jan - 12 Jan 2026
Fullerton Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (3)
"Really happy with our stay and the way we felt at this hideaway "
United States
Edwin
The price is ₹9,650
₹10,614 total
includes taxes & fees
21 Dec - 22 Dec
Hideaway Inn Mt. Snow

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
This inviting Perkinsville inn offers free Wi-Fi, breakfast and parking. Unwind with drinks at the bar/lounge or savour a meal at the restaurant. North Springfield Lake and Stoughton Pond Recreation Areas await nearby.

"The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. "
United States
Joshua
The Inn at Weathersfield

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1001)
This hotel offers quiet rooms and a peaceful environment near the Ashuelot River. Enjoy complimentary breakfast, WiFi, and parking. Guests love the helpful staff and convenient location. Visit the 24-hour fitness centre or unwind with a drink at the bar after exploring nearby attractions.

"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ₹11,643
₹12,633 total
includes taxes & fees
21 Dec - 22 Dec
Best Western Plus Keene Hotel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1002)
"Nice motel. "
United States
Richard
The price is ₹10,321
₹11,353 total
includes taxes & fees
27 Dec - 28 Dec
The Putney Inn

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (966)
Escape to this quiet retreat with an indoor pool and fitness centre near Ashuelot River. Just minutes from local shops and eateries, this hotel offers free breakfast, WiFi, and parking. The helpful staff ensures a comfortable stay for business or leisure travellers.

"The room was perfect, and the food was great "
United States
Paul
The price is ₹10,519
₹11,413 total
includes taxes & fees
24 Dec - 25 Dec
Keene Elm City Hotel, an Ascend Collection Hotel

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
The price is ₹16,246
₹17,627 total
includes taxes & fees
1 Jan - 2 Jan 2026
Fairfield Inn & Suites by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1001)
Stylish accommodation in Keene City centre, close to Colonial Theatre and Central Square. Enjoy a refreshing swim in the indoor pool, grab a bite at the coffee shop, then unwind at the bar. Free WiFi and parking make exploring the area convenient.

"Very comfortable and clean."
United States
Christina
The price is ₹16,073
₹17,439 total
includes taxes & fees
26 Dec - 27 Dec
Courtyard by Marriott Keene Downtown

Brook Bound Inn

Brook Bound Inn
2.0 star property
Wilmington
9.6 out of 10, Exceptional, (11)
Brook Bound Inn offers a charming Vermont retreat just minutes from Mount Snow. Enjoy snowmobiling on-site, then relax in the seasonal outdoor pool. With free WiFi and parking, this golf hotel puts North Branch Deerfield River adventures within easy reach.

"Great property. Amazing views!"
United States
Ryan
Brook Bound Inn

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (354)
Free breakfast, parking, and 24-hour fitness centre make this Keene hotel a great choice. Swim in the indoor pool or request room service after exploring nearby Cheshire Children's Museum. Travellers praise the helpful staff and morning meal.

"Clean comfy nice staff "
United States
Katherine
The price is ₹14,863
₹16,127 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Keene

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (806)
Tucked away in Springfield, this tranquil hotel offers a refreshing indoor swimming experience and fitness centre. Guests can explore nearby Baltimore Covered Bridge while enjoying free breakfast, WiFi, and parking throughout their stay.

"so clean and friendly it was a perfect stay!"
United States
Colette
The price is ₹13,582
₹14,941 total
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Springfield Hotel

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (608)
This Manchester Centre hotel offers a seasonal outdoor pool and free bike rentals to explore nearby hiking trails. Just minutes from Bromley Mountain for skiing enthusiasts, with complimentary WiFi and parking. Guests praise the helpful staff and clean, comfortable rooms.

"Great place to stay"
United States
Brian
The price is ₹11,103
₹13,194 total
includes taxes & fees
11 Jan - 12 Jan 2026
Aspen At Manchester

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (780)
Surrounded by Green Mountains, this Manchester Centre hotel offers a seasonal outdoor pool and free breakfast. Hike nearby trails or enjoy skiing at Bromley Mountain. Spacious rooms provide comfort after exploring Dana L. Thompson Memorial Park.

"Room very clean comfortable and quiet "
United States
Patty
The Manchester View

The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very good, (328)
Beautifully situated with easy access to transport, this charming hotel offers free WiFi and parking. Outdoor enthusiasts will appreciate nearby hiking trails, kayaking, and mountain biking opportunities, with Muckross State Park just a short drive away.

"nice folks, practical place to stay. "
United States
Mark
The price is ₹14,458
₹15,904 total
includes taxes & fees
21 Dec - 22 Dec
The Hartness House

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (928)
Located minutes from Brattleboro Station, this welcoming hotel offers a relaxing hot tub and fitness centre for unwinding after exploring. Enjoy the complimentary breakfast before visiting nearby United States Navy Seabee Bridge or grabbing coffee at the café.

"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is ₹13,107
₹14,417 total
includes taxes & fees
26 Dec - 27 Dec
Hampton Inn Brattleboro

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (71)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is ₹15,795
₹17,374 total
includes taxes & fees
23 Dec - 24 Dec
The Inn At Quail Run

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
Manchester Center
8.4 out of 10, Very good, (866)
Surrounded by Vermont's natural beauty, this Manchester Centre hotel offers a golf course minutes from Bromley Mountain Ski Resort. Guests enjoy the hot tub, American dining at Clove + Maple, and complimentary breakfast while exploring nearby Lye Brook Falls.

"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
United States
Amanda
The price is ₹9,032
₹11,408 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Palmer House Resort, an Ascend Collection Hotel

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (741)
Located minutes from Brattleboro Station, this welcoming hotel offers free breakfast, WiFi, and parking. Work out in the fitness centre before dining at the on-site restaurant. United States Navy Seabee Bridge and Brattleboro Bowl are nearby.

"Price, clean and spacious room, comfy bed."
United States
June
The price is ₹10,105
₹11,115 total
includes taxes & fees
22 Dec - 23 Dec
Comfort Inn & Suites Brattleboro I-91

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1000)
Set in Brattleboro, this charming inn sits near hiking trails and winter sports activities. Enjoy free continental breakfast each morning, complimentary WiFi, and parking. The United States Navy Seabee Bridge and Brattleboro Bowl are just minutes away.

"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is ₹8,036
₹8,840 total
includes taxes & fees
24 Dec - 25 Dec
The Covered Bridge Inn
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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

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. Pointe at Castle Hill Resort and Grand Summit Resort, A Vail Resorts Property 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. A top sight in the area is Stratton Mountain Resort. 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. Additionally, you'll find Stratton Mountain Resort 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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