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Our top choices for Chester hotels

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (410 reviews)
  • cleanliness
    Traditional Vermont charmer serves farm-fresh meals near historic sites.
"Great staff and service. "
United States
Chris
The price is NT$4,082
NT$4,449 total
includes taxes & fees
Jan 25 - Jan 26
Fullerton Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (109 reviews)
  • cleanliness
    Find tranquility near hiking trails in Chester with a delicious breakfast included.
"So great all around!"
United States
Janet
The price is NT$8,918
NT$9,721 total
includes taxes & fees
Jan 28 - Jan 29
Stone Hearth Inn and Eatery

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (415 reviews)
  • cleanliness
    Experience Vermont comfort close to Stratton and Bromley Mountain ski resorts.
"Gem of an older ski bed n breakfast "
United States
Martin
Bromley View Inn

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, (880 reviews)
  • cleanliness
    Refined mountain retreat with indoor and seasonal outdoor pools and golf course.
"Rooms were spotless and staff was great!"
United States
Helen
The price is NT$2,848
NT$3,654 total
includes taxes & fees
Jan 29 - Jan 30
The Palmer House Resort, an Ascend Collection Hotel

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (802 reviews)
  • cleanliness
    Tranquil mountain retreat with outdoor pool and trails, steps from skiing.
"Great staff, huge clean room, tasty continental breakfast."
United States
Carey
The Manchester View

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, (979 reviews)
  • cleanliness
    Modern hotel with a convenient location in Keene near shopping and dining.
"Reasonably priced and clean."
United States
Justin
The price is NT$3,924
NT$4,257 total
includes taxes & fees
Jan 25 - Jan 26
Keene Elm City Hotel, an Ascend Collection Hotel

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Stay connected in the Green Mountains at this welcoming Brattleboro hotel.
"Very clean room and super friendly staff!"
United States
Joanne
The price is NT$4,683
NT$5,151 total
includes taxes & fees
Jan 29 - Jan 30
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (758 reviews)
  • cleanliness
    Comfortable rooms and helpful staff await in Brattleboro near I-91.
"The room was clean and the staff was wonderful"
United States
Julianne
The price is NT$4,196
NT$4,616 total
includes taxes & fees
Jan 26 - Jan 27
Comfort Inn & Suites Brattleboro I-91

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,001 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
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, (1,001 reviews)
  • cleanliness
    Peaceful stay in Keene with included breakfast and convenient river access.
"Great stay pool was very nice"
United States
Patrick
The price is NT$4,396
NT$4,769 total
includes taxes & fees
Jan 25 - Jan 26
Best Western Plus Keene Hotel

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (909 reviews)
  • cleanliness
    Picturesque Woodstock retreat offers free bikes, hiking trails, and winter sports.
"Wonderful place to stay!"
United States
Robin
The price is NT$3,839
NT$4,561 total
includes taxes & fees
Jan 27 - Jan 28
The Shire Woodstock

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (479 reviews)
  • cleanliness
    Discover tranquil mountain lodging with a seasonal pool and trails nearby.
"Instant check-in and check-out Very responsive and friendly staff. Clean and well maintained. Everything you need is provided. The room is spacious, and the beds are comfortable."
United States
Olga
The price is NT$3,481
NT$3,829 total
includes taxes & fees
Jan 25 - Jan 26
Black Mountain Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,000 reviews)
  • cleanliness
    Rustic Vermont hotel with hiking and snowboarding access, plus free breakfast.
"Easy check in and good parking"
United States
nicholas
The price is NT$2,816
NT$3,098 total
includes taxes & fees
Feb 8 - Feb 9
The Covered Bridge Inn

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (936 reviews)
  • cleanliness
    Experience comfort at this Brattleboro hotel with free breakfast and convenient amenities.
"Good breakfast, great staff and very good location "
United States
Valdeci
The price is NT$4,644
NT$5,109 total
includes taxes & fees
Jan 30 - Jan 31
Hampton Inn Brattleboro

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Riverside escape with indoor pool and bistro dining just steps from Woodstock.
"Brilliant stay"
United States
Enrico
The price is NT$7,499
NT$9,409 total
includes taxes & fees
Feb 12 - Feb 13
On The River Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (246 reviews)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (343 reviews)
  • cleanliness
    Charming Vermont B&B with free breakfast near skiing and Southern History Museum.
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is NT$4,981
NT$5,479 total
includes taxes & fees
Feb 8 - Feb 9
Colonel Williams Inn

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (622 reviews)
  • cleanliness
    Scenic Vermont getaway with outdoor pool near Bromley Mountain Ski Resort.
"Super clean and modern rooms, excellent location, scenic views… "
United States
Fernando
The price is NT$2,759
NT$3,383 total
includes taxes & fees
Jan 26 - Jan 27
Aspen At Manchester

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (556 reviews)
  • cleanliness
    Great ski lodge with comfortable, quiet rooms just outside charming Woodstock.
"So much love and thoughtfulness was put into our room and common area. Comfy beds, little touches like free snacks and goodies and super clean room. It's also super dog friendly! There's also a fantastic little coffee stand walking distance. "
United States
JILL
The price is NT$2,307
NT$4,515 total
includes taxes & fees
Jan 26 - Jan 27
Sleep Woodstock Motel

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (636 reviews)
  • cleanliness
    Experience riverside tranquility with mountain views in New Hampshire.
"Scenic balcony. Friendly staff. We had a lovely stay. "
United States
Travis
The price is NT$5,098
NT$5,531 total
includes taxes & fees
Jan 29 - Jan 30
Riverside Hotel, an Ascend Collection Hotel
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. Learn more about Chester
Learn more about Chester

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 Adventures: Chester offers excellent skiing options and a variety of outdoor activities, perfect for adventure seekers.
  • Charming Downtown: Stroll through Chester's historic streets filled with quirky shops and a vibrant atmosphere.
  • Cultural Experiences: Explore local parks, historical museums, and engage with friendly locals for a rich cultural experience.
  • Family-Friendly Accommodations: Enjoy a range of lodging options, from cozy bed and breakfasts to unique agritourism properties.
  • Budget-Friendly Options: Chester provides affordable recreational opportunities, ensuring a memorable vacation for every traveler.

Find great hotels near Chester

Discover the charm of Chester, Vermont, where a variety of lodging options await you, including cozy bed and breakfasts and unique agritourism properties. Perfect for families, adventurers, and pet lovers, Chester's hotels offer the ideal retreat with essential amenities and warm hospitality. Explore local hotel reviews to find the perfect fit for your stay and enjoy a memorable vacation experience in this picturesque New England town.

  • Best Western Springfield Hotel: This welcoming hotel offers a pet-friendly experience, making it ideal for travelers who wish to bring their furry companions along. Located 12.9km from Chester, the Best Western Springfield Hotel features comfortable accommodations with amenities designed for both relaxation and convenience. Guests appreciate the hotel's accommodating pet policy, which allows dogs on the property. With a focus on providing a friendly and accessible atmosphere, this hotel is perfect for those looking to explore the scenic beauty of Vermont while enjoying the company of their pets.
  • Pointe at Castle Hill Resort: A 3.5-star gem situated 14.5km from Chester, this resort embodies adventure and relaxation. With a plethora of onsite and nearby activities, including snow tubing, ziplining, and mountain biking, guests will find plenty of excitement. After an action-packed day, unwind at the full-service spa, where treatments like aromatherapy and deep tissue massage await. Perfect for business travelers and thrill-seekers alike, the Pointe at Castle Hill Resort combines comfort with a touch of adventure, making it a distinctive choice for your stay.
  • Jackson Gore Village: Nestled 20.9km from Chester, Jackson Gore Village is a family-friendly retreat that offers a unique blend of adventure and leisure. Guests can enjoy a variety of activities, including onsite snow tubing and skiing, as well as family-friendly amenities like a mini-golf course and playground. This 3-star accommodation is perfect for families seeking fun and excitement together. The focus on adventure and community makes Jackson Gore Village an attractive destination for those looking to create lasting memories in the beautiful Vermont landscape.

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's historic streets and vibrant atmosphere, where friendly locals welcome you. Enjoy recreational opportunities like skiing and various outdoor activities, all while appreciating the town's budget-friendly options. Whether you're seeking luxury or a laid-back vibe, Chester has something for every traveler, making it an ideal spot for your vacation.

  • Ludlow: Located 17.7km from Chester, Ludlow is a vibrant city known for its seasonal charm, particularly during the winter months when outdoor enthusiasts flock to its ski resorts. With a strong emphasis on adventure, Ludlow offers thrilling opportunities for skiing and other winter sports against a backdrop of picturesque mountains and valleys. Visitors can explore the nearby lakes, making it a perfect spot for both ski lovers and nature enthusiasts. The ski fields here are easily accessible, providing a fun-filled experience for travelers of all skill levels.
  • Springfield: Just 9.7km from Chester, Springfield is a year-round destination that attracts visitors with its diverse outdoor activities. The city sees peaks in travel during February, July, and September, drawing those eager for both skiing and exploration. With proximity to national state parks, lakes, and mountains, Springfield offers a rich landscape for hiking, skiing, and other outdoor adventures. Its vibrant community and local attractions make it a delightful stop for anyone looking to immerse themselves in the beauty of Vermont.
  • Grafton: Also located 9.7km from Chester, Grafton is a charming city that shines in the summer and early fall months, welcoming travelers seeking outdoor experiences. Known for its scenic ski fields and lush valleys, Grafton is ideal for those wanting to embrace nature year-round. The area’s stunning lakes and mountainous terrain provide a beautiful backdrop for an array of activities, including hiking, skiing, and simply enjoying the fresh Vermont air. Grafton's quaint atmosphere and outdoor offerings make it a must-visit for adventurers.

Things to do near Chester

Chester, Vermont is the perfect destination for adventure seekers and ski enthusiasts. Enjoy outdoor adventures in the scenic landscape, explore quirky shops that offer unique finds, and take advantage of the excellent skiing options available at local ski fields and resorts. Whether you're hitting the slopes or wandering through charming boutiques, Chester promises a memorable vacation experience.

Shopping

In Chester, visit the Vermont Country Store for unique gifts and souvenirs just 9.7km away. My Minds Design, also 9.7km away, offers creative items. If you're up for a drive, check out the West River Farmers Market, located 17.7km away, for a vibrant local shopping experience.

Recreation

At Fox Run Golf Course, enjoy a scenic round of golf surrounded by beautiful landscapes. The Ice House Ice Skating offers a serene atmosphere for relaxation and fun on the ice. For more golfing, Stratton Mountain Golf Course provides a challenging experience with stunning outdoor views.

Adventure

At Okemo Mountain Resort, experience thrilling skiing adventures in a vibrant atmosphere, located 17.7km from Chester. The Solitude Express Ski Lift, 19.3km away, offers breathtaking views as you ascend. For a unique perspective, try Morningside Flight Park, also 19.3km from Chester, where scenic flights await you.

Nightlife

Experience a charming evening in Chester with a visit to the Weston Playhouse, just 16.1km away, for a romantic theater performance. For family fun, check out Maple Lanes, an arcade AdventureZone located 22.5km away. Don’t miss the Bellows Falls Opera House, 19.3km from Chester, for more cultural 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, consider visiting during the cheaper months of April to May and November, with Tuesdays being the least expensive days for accommodation. Use Expedia to customize your travel preferences and find eco-friendly hotels at lower rates by sorting prices from lowest to highest. Additionally, combine your hotel stay, flights, and activities for package deals to maximize savings. Explore free local attractions and utilize affordable public transport options to navigate the area 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: Utilize Expedia’s search tool to customize your travel preferences, such as your budget, favored location, and the type of hotel you desire. For instance, selecting the Eco-certified option will show you sustainable and eco-friendly accommodations that are currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay 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 and adventure enthusiasts, offering a range of outdoor activities and sports. Visitors can explore local parks, national and state parks, and historical museums, making it a perfect spot for those seeking cultural experiences and family fun. Whether you're hitting the slopes or enjoying nature, Chester has something for everyone to enjoy during their stay.

  • Vermont Museum of Mining and Minerals: Located 9.7km from Chester, this museum offers a fascinating glimpse into Vermont's geological history. With engaging exhibits focusing on minerals and mining, it provides a family-friendly atmosphere perfect for all ages.
  • Lowell Lake State Park: Just 14.5km away, this stunning state park is an outdoor lover's paradise. Experience breathtaking scenery and a variety of recreational activities, from hiking to fishing, making it ideal for adventure seekers.
  • Grafton Historical Society: Situated 9.7km from Chester, this history museum immerses visitors in the rich cultural heritage of the Grafton area. It's a delightful stop for those interested in local history and traditions.

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

To visit Chester, Vermont, you have several airport options. Lebanon Municipal Airport (LEB) is located 46.7km away, with nearby hotels like the 4-star Hanover Inn Dartmouth and the 3-star Hotel Coolidge, both offering convenient access. Rutland Southern Vermont Regional Airport (RUT) is 40.2km from Chester, with quality options including the 3.5-star Killington Mountain Lodge. For closer access, Springfield's Hartness State Airport (VSF) is only 11.3km away, featuring the 4-star Inn at Weathersfield and the 3.5-star Pointe at Castle Hill Resort. Each hotel provides various transportation services to ensure a smooth journey to and from the airports.

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.
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 pet-friendly accommodation in Chester?
Motel in the Meadow is a top pet-friendly option for your stay. See more pet-friendly hotel accommodations in Chester.
What are some accommodations with pools in Chester?
Pointe at Castle Hill Resort: Offers a full-service spa, an indoor pool, and free self parking. Woodstock Inn & Resort and Kimpton Taconic Hotel by IHG 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. Top sights around the area include Okemo Mountain Resort and Stratton Mountain Resort. In Chester, there are 66 hotels and other accommodations to choose from. Find out more about Chester.
What should I see while I'm in Chester?
Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are fun for everyone. Additionally, you'll find Okemo Mountain Resort and 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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