Find hotels in Chester, VT from AED 335

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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 AED 767
AED 836 total
includes taxes & fees
29 Dec - 30 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 AED 474
AED 516 total
includes taxes & fees
5 Jan - 6 January 2026
Fullerton Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (4)
"Really happy with our stay and the way we felt at this hideaway "
United States
Edwin
The price is AED 484
AED 532 total
includes taxes & fees
4 Jan - 5 January 2026
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 savor 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

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1001)
"The room was okay for a quick stop to rest. "
United States
Janice
The Putney Inn

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 center or unwind with a drink at the bar after exploring nearby attractions.

"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is AED 511
AED 554 total
includes taxes & fees
25 Dec - 26 Dec
Best Western Plus Keene Hotel

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, (967)
Escape to this quiet retreat with an indoor pool and fitness center 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 travelers.

"The room was perfect, and the food was great "
United States
Paul
The price is AED 433
AED 469 total
includes taxes & fees
28 Dec - 29 Dec
Keene Elm City Hotel, an Ascend Collection Hotel

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 center. 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 AED 559
AED 615 total
includes taxes & fees
5 Jan - 6 January 2026
Best Western Springfield 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 AED 661
AED 717 total
includes taxes & fees
1 Jan - 2 January 2026
Fairfield Inn & Suites 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

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1002)
Stylish accommodations in Keene Downtown, 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 AED 661
AED 717 total
includes taxes & fees
30 Dec - 31 Dec
Courtyard by Marriott Keene Downtown

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (613)
This Manchester Center 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.

"Super clean and modern rooms, excellent location, scenic views… "
United States
Fernando
The price is AED 363
AED 439 total
includes taxes & fees
12 Jan - 13 January 2026
Aspen At Manchester

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1000)
Step into comfort at this Manchester Center hotel, just minutes from shopping destinations. The indoor pool and hot tub offer year-round relaxation, while rooms include convenient refrigerators and microwaves. Enjoy complimentary breakfast, WiFi, and parking before exploring nearby attractions.

"Great time "
United States
Paul
The price is AED 479
AED 527 total
includes taxes & fees
11 Jan - 12 January 2026
Hampton Inn and Suites Manchester

The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very Good, (329)
Beautifully situated with easy access to transportation, 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 AED 613
AED 674 total
includes taxes & fees
25 Dec - 26 Dec
The Hartness House

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (782)
Surrounded by Green Mountains, this Manchester Center 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 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 Center 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 AED 372
AED 469 total
includes taxes & fees
13 Jan - 14 January 2026
The Palmer House Resort, an Ascend Collection Hotel

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 AED 643
AED 707 total
includes taxes & fees
25 Dec - 26 Dec
The Inn At Quail Run

The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (563)
Surrounded by Vermont's beauty, this Manchester Center lodge offers a refreshing seasonal pool and outdoor tennis court. Enjoy free breakfast, parking, and WiFi while being close to Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park.

"Great little inn. Has a wonderful home feeling. The owners are super friendly and made the stay a great experience."
United States
Holly
The price is AED 679
AED 747 total
includes taxes & fees
4 Jan - 5 January 2026
The Olympia Lodge

Toll Road Inn

Toll Road Inn
2.0 star property
Manchester Center
9.0 out of 10, Wonderful, (489)
This charming hotel offers a seasonal outdoor pool and relaxing hot tub after mountain adventures. Located in Manchester Center with free WiFi and parking, it's just a short drive to Bromley Mountain and Gander Gallery.

"Clean and convenient room, good experience."
United States
Mingyang
The price is AED 525
AED 578 total
includes taxes & fees
4 Jan - 5 January 2026
Toll Road Inn

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
Walking distance to Central Square, this inviting guesthouse offers complimentary WiFi and self parking. Enjoy the outdoor picnic area after exploring nearby attractions like CC&H Framing and Pepper Pete's Hot Shop.

"Very helpful, kind staff"
United States
Paitris
The Burrell House
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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

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

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

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 visit based on reviews is Fullerton Inn. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental that Chester has to offer?
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: Visitors like this Chester vacation home rental. It is located on the waterfront and has a balcony, a garden, 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. Kick off your shoes and enjoy yourself with a selection of games and a hot tub. 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 Bonnie's Bundles Dolls and DaVallia Art & Accents 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?
Motel in the Meadow is a top pet-friendly option for your stay. Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub is another good option for a stay with 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. Pointe at Castle Hill Resort and Grand Summit Resort, A Vail Resorts Property 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. A top sight in the area is Stratton Mountain Resort. In Chester, there are 67 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. Additionally, you'll find Stratton Mountain Resort 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.

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