Find hotels in Chester, VT from SAR 342

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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)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is SAR 783
SAR 854 total
includes taxes & fees
8 Jan - 9 January 2026
Stone Hearth Inn and Eatery

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (403)
"Lovely stay"
United States
Christine
The price is SAR 484
SAR 527 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 SAR 494
SAR 544 total
includes taxes & fees
8 Jan - 9 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)
"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)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is SAR 521
SAR 566 total
includes taxes & fees
30 Dec - 31 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, (968)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is SAR 442
SAR 479 total
includes taxes & fees
31 Dec - 1 January 2026
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)
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is SAR 571
SAR 628 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 SAR 675
SAR 733 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)
"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, (1001)
"Very comfortable and clean."
United States
Christina
The price is SAR 675
SAR 733 total
includes taxes & fees
1 Jan - 2 January 2026
Courtyard by Marriott Keene Downtown

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (613)
"Super clean and modern rooms, excellent location, scenic views… "
United States
Fernando
The price is SAR 373
SAR 451 total
includes taxes & fees
4 Jan - 5 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, (1002)
"Great time "
United States
Paul
The price is SAR 489
SAR 538 total
includes taxes & fees
4 Jan - 5 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)
"nice folks, practical place to stay. "
United States
Mark
The price is SAR 612
SAR 673 total
includes taxes & fees
30 Dec - 31 Dec
The Hartness House

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (782)
"Staff and room was clean "
United States
Melissa
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)
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
United States
Amanda
The price is SAR 379
SAR 479 total
includes taxes & fees
26 Jan - 27 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 SAR 844
SAR 928 total
includes taxes & fees
5 Jan - 6 January 2026
The Inn At Quail Run

The Olympia Lodge

The Olympia Lodge
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (563)
"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 SAR 694
SAR 763 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)
"Clean and convenient room, good experience."
United States
Mingyang
The price is SAR 536
SAR 590 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, (156)
"Very helpful, kind staff"
United States
Paitris
The Burrell House
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 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

  • Outdoor Adventure: Chester is a paradise for outdoor enthusiasts, offering skiing, snowboarding, and scenic ski fields for winter sports lovers.
  • Charming Downtown: Explore quirky shops and local boutiques that provide a unique shopping experience in the heart of Chester.
  • Cultural Experiences: Visit parks, state parks, and history museums for a blend of outdoor activities and cultural enrichment.
  • Cozy Accommodations: Enjoy a range of charming hotels, agritourism properties, and cozy bed & breakfasts suited for every traveler.
  • Family-Friendly Fun: Chester offers budget-friendly options perfect for family getaways and connecting with nature.

Find great hotels near Chester

Explore charming hotel options in Chester, Vermont, where you'll find a delightful mix of agritourism properties and cozy bed & breakfasts. Whether you're seeking family-friendly accommodations, pet-friendly stays, or adventurous experiences, Chester has something to offer every traveler. Read reviews and discover the best Chester inns and hotels to make your visit memorable.

  • Best Western Springfield Hotel: A welcoming haven for pet lovers, the Best Western Springfield Hotel is located 12.9km from Chester. This hotel offers a friendly atmosphere and a range of amenities designed for travelers seeking a pet-friendly experience. With a pet policy that includes dogs only and waived fees for service animals, guests can enjoy their stay without leaving their furry friends behind. The hotel's comfortable accommodations and convenient location make it an ideal choice for families and individuals looking for a relaxing getaway.
  • Pointe at Castle Hill Resort: Nestled 14.5km from Chester, the Pointe at Castle Hill Resort is a 3.5-star hotel that caters to adventure enthusiasts and business travelers alike. This resort is perfect for those seeking a thrilling experience, offering a variety of adventure sports such as snow tubing, rafting, and snowboarding nearby. Guests can unwind in the full-service spa or enjoy the indoor pool, ensuring relaxation after a day of activities. With its blend of adventure and comfort, this resort promises an unforgettable stay.
  • Jackson Gore Village: Located 20.9km from Chester, Jackson Gore Village is a charming 3-star hotel that focuses on golf-themed and adventure experiences. Here, guests can immerse themselves in golf activities and explore nearby mountain biking, hiking, and skiing options. The property also features a full-service spa and indoor pool, providing a perfect retreat after an action-packed day. With its emphasis on recreation and relaxation, this hotel is ideal for travelers looking for a balanced vacation filled with both adventure and leisure.

Where to stay near Chester

Chester, Vermont, offers a perfect blend of adventure and relaxation for travelers. From skiing and outdoor sports to exploring the charming downtown, visitors can enjoy a weekend getaway filled with recreational opportunities. The friendly atmosphere, combined with historical sites, makes Chester an ideal destination for those seeking both budget-friendly options and a touch of luxury. Discover the unique vibes of this picturesque town and its surrounding regions, where every traveler can find something special.

  • Ludlow: Located 17.7km from Chester, Ludlow is a charming city known for its vibrant winter sports scene. The town attracts visitors primarily from December to February, making it a popular destination for skiing enthusiasts. With its stunning mountain views and access to ski fields and resorts, Ludlow offers an exhilarating adventure experience. In addition to skiing, visitors can explore local lakes and valleys, making it a picturesque setting for both winter sports and summer activities. Whether you're a thrill-seeker or a nature lover, Ludlow has something to offer.
  • Springfield: Just 9.7km away from Chester, Springfield is a bustling city that draws travelers year-round, with peak visitor numbers in February, July, and September. Known for its adventurous spirit, Springfield is a hotspot for skiing and outdoor sports, featuring several ski fields and resorts nearby. The city is also home to beautiful lakes and mountains, along with the nearby national state park, which offers opportunities for hiking and exploring the great outdoors. Springfield provides a dynamic travel experience that balances adventure with serene nature.
  • Grafton: Only 9.7km from Chester, Grafton is a delightful city perfect for those who love outdoor activities. While visitor numbers peak in July and September to October, Grafton welcomes travelers throughout the year, particularly those seeking skiing and adventure. The city is surrounded by stunning lakes, valleys, and mountains, creating an ideal backdrop for outdoor exploration. Grafton’s charm lies in its small-town atmosphere coupled with accessible adventure, making it a fantastic choice for a memorable getaway.

Things to do near Chester

Chester, Vermont, is perfect for outdoor enthusiasts seeking adventure and sports vacations. Visitors can enjoy various skiing options at local ski resorts and explore the scenic ski fields. In addition to winter sports, Chester boasts quirky shops that offer a unique shopping experience. Whether you're hitting the slopes or browsing for unique finds, Chester provides a delightful mix of outdoor excitement and local charm.

Shopping

For a delightful shopping experience in Chester, visit the Vermont Country Store and My Minds Design, both located 9.7km away. If you're up for a drive, check out the West River Farmers Market, which is 17.7km away and offers a vibrant local atmosphere.

Recreation

Experience a round of golf at Fox Run Golf Course, where you can enjoy the beautiful outdoor scenery and sports atmosphere, just 19.3km from Chester. Alternatively, unwind at The Ice House Ice Skating, a recreation center 20.9km away, perfect for relaxation and wellness vibes.

Play a round at Stratton Mountain Golf Course, located 20.9km from Chester, offering a vibrant outdoor experience and sports activities. Whether you’re golfing or skating, these venues provide a refreshing escape into nature and recreation.

Adventure

Experience the thrill of skiing at Okemo Mountain Resort, located 17.7km from Chester, where you can enjoy diverse slopes and vibrant sports vibes. For a scenic aerial view, Morningside Flight Park, 19.3km away, offers an exhilarating flight experience amidst stunning landscapes.

Nightlife

Experience the charm of Chester's nightlife at the Weston Playhouse for captivating performances or visit the Bellows Falls Opera House for a romantic evening filled with culture. For a fun twist, head to Maple Lanes for arcade adventures that promise excitement and entertainment.

*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, plan your visit during the cheaper months of April to May or November, and consider staying on Tuesdays for the best rates. Utilize Expedia to compare room rates and search for eco-certified hotels to find budget-friendly options. Look for package deals that combine your hotel, flights, and activities for additional savings. Exploring free outdoor activities and utilizing public transport can also help stretch your budget while enjoying the beautiful surroundings of Chester.

  • 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 tailor your options based on your budget, desired location, and preferred type of hotel. For instance, selecting the Eco-certified filter will show you a selection of sustainable and environmentally friendly hotels currently available. To find the best prices and deals, be sure to sort 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 deal.

Find the best attractions near Chester

Chester, Vermont, offers a fantastic vacation for adventure and sports enthusiasts, particularly in skiing. Visitors can explore various attractions, including parks, state parks, and history museums, which provide a blend of outdoor activities and cultural experiences. Perfect for families and those seeking to connect with nature, Chester promises exciting adventures and enriching visits to its local points of interest.

  • Vermont Museum of Mining and Minerals: Located 9.7km from Chester, this unique natural history museum offers a fascinating glimpse into Vermont's mining history. Families will enjoy interactive exhibits showcasing various minerals and gemstones, as well as the cultural significance of mining in the region.
  • Lowell Lake State Park: About 14.5km from Chester, this stunning national state park is perfect for outdoor enthusiasts. With beautiful scenery, hiking trails, and opportunities for adventure, visitors can immerse themselves in nature and enjoy activities like canoeing and birdwatching.
  • Grafton Historical Society: Situated 9.7km away, this history museum provides a charming look into the local culture. With exhibits detailing the area's rich heritage, it’s a great stop for those interested in Vermont's historical narratives.

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

For your vacation to Chester, Vermont, you have several airport options. LEBanon Municipal Airport (LEB) is 46.7km away, with nearby hotels like the 4-star Hanover Inn Dartmouth, located 8.0km from the airport, and the 3-star Hotel Coolidge, just 3.2km away. RUTland Southern Vermont Regional Airport (RUT) is 28.0km from Chester, and you can stay at the Killington Mountain Lodge, a 3.5-star hotel situated 17.7km from the airport. The closest option is Hartness State Airport (VSF) in Springfield, only 11.3km away, with excellent accommodations like the 4-star Inn at Weathersfield, just 1.6km from the airport.

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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