Chester Hotels

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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, (435 reviews)
"The staff were incredible and the property have the perfect vibes for a ski trip. The food was great and everything was very clean and comfy."
United States
Rob
The price is P8,565
P9,336 total
includes taxes & fees
May 30 - May 31
Fullerton Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (118 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is P12,861
P14,019 total
includes taxes & fees
Jun 11 - Jun 12
Stone Hearth Inn and Eatery

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (358 reviews)
"Very nice motel "
United States
Doug
The price is P4,622
P5,084 total
includes taxes & fees
Jun 1 - Jun 2
Brittany Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (580 reviews)
"Quiet, well kept, comfortable, convenient."
United States
Elisabeth
The price is P4,492
P8,454 total
includes taxes & fees
Jun 3 - Jun 4
Sleep Woodstock Motel

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (442 reviews)
"We had an enjoyable stay and would stay again. "
United States
Donna
The price is P4,908
P5,399 total
includes taxes & fees
May 31 - Jun 1
Bromley View Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (39 reviews)
"The hot tub was so amazing"
United States
Mark
The price is P8,041
P8,765 total
includes taxes & fees
May 31 - Jun 1
Four Columns Inn

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (502 reviews)
"Friendly services and clean rooms!"
United States
Eric
The price is P6,778
P7,354 total
includes taxes & fees
May 31 - Jun 1
Claremont Motor Lodge

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (170 reviews)
"Self check-in and checkout. Room was very clean but a bit too much potpourri for my allergies. Will stay here again when in Keene. "
United States
Charles
The price is P7,662
P8,543 total
includes taxes & fees
Jun 2 - Jun 3
The Burrell House

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (126 reviews)
"Staff very helpful. Everything was very clean"
United States
Patrick
The price is P8,263
P9,090 total
includes taxes & fees
Jun 14 - Jun 15
Chalet 239

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (281 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is P9,705
P10,676 total
includes taxes & fees
Jun 3 - Jun 4
The Jackson

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
The price is P9,698
P10,668 total
includes taxes & fees
Jun 1 - Jun 2
Colonel Williams Inn

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (79 reviews)
"Great location, service and restaurant "
United States
LUDJANE
The price is P10,920
P14,170 total
includes taxes & fees
May 31 - Jun 1
The Inn at Weathersfield

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (985 reviews)
"Clean room, great included breakfast, staff was nice and overall was just a good time"
United States
Savanna
The price is P7,529
P8,282 total
includes taxes & fees
Jun 7 - Jun 8
Hampton Inn Brattleboro

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (887 reviews)
"Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!"
United States
Sharon
The price is P7,622
P8,385 total
includes taxes & fees
Jun 2 - Jun 3
Latchis Hotel

Stanford House

Stanford House
2.5 star property
Manchester Center
9.2 out of 10, Wonderful, (74 reviews)
"Perfect for a quick overnight to go skiing at Stratton."
United States
Benjamin
The price is P6,932
P8,329 total
includes taxes & fees
Jun 2 - Jun 3
Stanford House

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.8 out of 10, Excellent, (72 reviews)
"Peaceful, historic property with amiable keepers."
United States
Elisabeth
The price is P11,646
P12,811 total
includes taxes & fees
Jun 1 - Jun 2
Lincoln Inn & Gallery

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.6 out of 10, Excellent, (1,002 reviews)
"Perfect for an overnight!"
United States
Lori
The price is P5,795
P6,375 total
includes taxes & fees
May 31 - Jun 1
The Putney Inn

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (859 reviews)
"Great place to stay"
United States
Daniel
The price is P10,482
P11,530 total
includes taxes & fees
Jun 9 - Jun 10
Best Western Springfield Hotel

Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.8 out of 10, (338 reviews)
"You can’t go wrong with the price. Close to many activities."
United States
Carolina
The price is P6,100
P6,619 total
includes taxes & fees
Jun 8 - Jun 9
Royal Inn Claremont

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (995 reviews)
"Rooms were clean, some wear noticeable. Staff very friendly and helpful."
United States
Paul
The price is P9,181
P11,109 total
includes taxes & fees
May 31 - Jun 1
The Black Bear Lodge at Stratton Mountain Resort
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

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester offers a plethora of opportunities for skiing and winter sports, making it a prime destination for adventure enthusiasts.
  • Charming Downtown: Explore the quaint downtown area filled with quirky shops, providing a unique shopping experience.
  • Cultural Experiences: Discover local history through museums and state parks, blending cultural enrichment with outdoor activities.
  • Relaxing Getaway: The town's friendly atmosphere and delightful lodging options make it perfect for a weekend retreat.
  • Pet-Friendly Options: Chester caters to all, including pet lovers, ensuring a welcoming experience for every traveller.

Find great hotels near Chester

Explore the delightful lodging options in Chester, Vermont, where you can choose from charming bed and breakfasts to unique agritourism properties. Catering to families, adventurers, and pet lovers alike, this picturesque area offers a variety of hotel services and facilities to ensure a memorable stay. Whether seeking hotel reviews or comfortable rooms, Chester promises an inviting retreat in the heart of New England.

  • Best Western Springfield Hotel: Nestled 12.9km from Chester, Best Western Springfield Hotel is a welcoming retreat ideal for pet lovers. This hotel embraces a pet-friendly ethos, allowing dogs to accompany their owners, making it perfect for those who prefer to travel with their furry friends. Guests appreciate the warm, comfortable atmosphere and the attentive service, which ensures a pleasant stay. Key amenities include a relaxing environment and convenient access to local attractions, making it a great choice for families and couples alike.
  • Pointe at Castle Hill Resort: Situated 14.5km from Chester, this 3.5-star rated hotel offers a blend of business and adventure with a touch of luxury. The Pointe at Castle Hill Resort boasts an extensive range of adventure sports, including skiing, horse riding, hiking, and zip-lining, perfect for thrill-seekers. After an action-packed day, guests can unwind at the full-service spa, offering treatments and an indoor pool. With its focus on relaxation and adventure, this resort is a fantastic choice for those looking to balance work and play.
  • Jackson Gore Village: Located 20.9km from Chester, Jackson Gore Village is a family-friendly haven designed for both adventure and relaxation. This 3-star rated property features ample activities for children, including a playground, mini-golf, and arcade game room, ensuring a delightful experience for younger guests. Adventure enthusiasts can enjoy onsite zip-lining and ski lessons, along with nearby hiking and snow tubing. Families will appreciate the welcoming atmosphere and spacious accommodations, making it an excellent choice for creating lasting holiday memories.

Where to stay near Chester

Chester, Vermont, is a charming destination perfect for a weekend getaway, offering a delightful blend of relaxation and adventure. Visitors can explore the quaint downtown area, indulge in recreational opportunities, and soak in the friendly atmosphere. Nearby regions provide a taste of luxury and historical charm, making it an ideal spot for travellers seeking both budget-friendly experiences and thrilling outdoor activities. Whether skiing or unwinding, Chester promises an unforgettable escape.

  • Ludlow: Nestled 17.7km from Chester, Ludlow is a vibrant city renowned for its outdoor adventures, especially in the winter months when skiing takes centre stage. The travel experience here is characterised by a mix of seasonal excitement, with visitor numbers peaking from December to February. Ludlow's picturesque landscape features stunning lakes, majestic mountains, and serene valleys, making it a perfect backdrop for skiing and sports enthusiasts. Popular venues include ski resorts that cater to both novices and experts alike, offering thrilling slopes and breathtaking views.
  • Springfield: Located a mere 9.7km from Chester, Springfield is a charming city that attracts visitors year-round with its diverse offerings. Known for its skiing and adventure sports, it sees a surge of tourists in February, July, and September. The city is surrounded by natural beauty, including lakes, mountains, and the nearby national state park, providing ample opportunities for exploration and outdoor activities. Whether you're seeking adrenaline-pumping experiences or tranquil moments in nature, Springfield has something for everyone.
  • Grafton: Just 9.7km from Chester, Grafton is a delightful city that combines outdoor adventure with serene landscapes. With a steady stream of visitors, particularly in July and the autumn months, Grafton is a prime destination for those looking to ski and enjoy the great outdoors. The area is dotted with enchanting lakes, valleys, and mountains, perfect for hiking or simply soaking in the stunning scenery. Grafton’s welcoming atmosphere and access to ski resorts make it an ideal spot for adventure seekers looking for both excitement and relaxation.

Things to do near Chester

Chester, Vermont, is a delightful destination for those seeking outdoor adventures and winter sports. Visitors can indulge in skiing at nearby resorts and explore various ski fields. Additionally, the town boasts quirky shops that offer a unique shopping experience, making it an ideal spot for a memorable holiday filled with both excitement and 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, head to the West River Farmers Market, situated 17.7km from Chester, offering a vibrant local atmosphere and unique finds.

Recreation

The Ice House Ice Skating, located 20.9km from Chester, offers a refreshing experience with its wellness and relaxation vibes, perfect for a leisurely day. Crown Point Golf Course, 12.9km away, invites you to enjoy outdoor sports in a picturesque setting, while Fox Run Golf Course, 19.3km distant, promises a delightful round amidst nature.

Adventure

Experience the thrill of skiing at Okemo Mountain Resort, located 17.7km from Chester, where you can enjoy a variety of slopes. For a unique ride, the Skywalker Carpet ski lift, also 17.7km away, offers easy access to the slopes. Don't miss the Tubing Park, 20.9km away, for exhilarating outdoor fun.

Nightlife

Experience the charm of the Weston Playhouse, a theatre 16.1km from Chester, offering delightful performances. For family fun, visit Maple Lanes, an arcade adventure zone 22.5km away. For thrill-seekers, try the Timber Ripper Mountain Coaster, an exhilarating ride located 20.9km from Chester.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chester

For a budget-friendly trip to Chester, Vermont, consider visiting during the cheaper months of April to May and November, avoiding the peak seasons of January to February and October. Book your stay on a Tuesday for the best rates and use Expedia's search tool to filter by budget and eco-friendly accommodations. Combine hotel, flight, and activity bookings for additional savings through package deals. Explore free local attractions and utilise public transport options to minimise travel expenses while enjoying the scenic beauty 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: Utilise Expedia's search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find 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 hotel reservation 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 skiing and adventure sports enthusiasts. Visitors can explore a variety of points of interest, including parks, state parks, and history museums, offering a rich blend of outdoor activities and cultural experiences. Whether you're seeking family-friendly adventures or a taste of local history, Chester provides a delightful array of attractions to suit every traveller's needs.

  • Hunter Gallery of Fine Art: Located 9.7km from Chester, this gallery showcases a diverse array of artworks, embodying a rich cultural atmosphere. Visitors can immerse themselves in the local art scene and engage with talented artists, making it a perfect spot for art enthusiasts.
  • The Nature Museum: Also situated 9.7km away, this eco-friendly centre offers an interactive experience focusing on environmental conservation. It features exhibits that highlight the region's natural history, making it ideal for those keen on sustainability and nature education.
  • General Parking: Though 17.7km from Chester, this landmark is vital for visitors, providing convenient access to various attractions in the area, ensuring a hassle-free exploration.

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

When visiting Chester, Vermont, you have several airport options. Rutland Southern Vermont Regional Airport (RUT) is located 40.2km away, with nearby hotels like the 3-star Cortina Inn and Days Inn by Wyndham, both offering free 24-hour airport shuttle services. Glens Falls Airport (GFL) is 82.1km from Chester, with lodgings such as the 4-star Lodges At Cresthaven and the 3.5-star Six Flags Great Escape Lodge, providing accessible shuttle services for a fee. Additionally, Lebanon Municipal Airport (LEB) is 46.7km away, and options like the Windsor Mansion Inn and Courtyard by Marriott Hanover Lebanon are conveniently located nearby, offering easy access to the airport.

Frequently asked questions

Where is the best place to stay in Chester?
Based on our traveler data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. Other good choices for your trip to the area are Woodstock Inn & Resort and Pointe at Castle Hill Resort. 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.
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?
Woodstock Inn & Resort: Provides a seasonal outdoor pool, an indoor pool, and 4 restaurants. Pointe at Castle Hill Resort and Kimpton Taconic Hotel by IHG are two additional hotels with an onsite pool. View all hotels with pools in Chester.
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. In Chester, there are 62 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. You'll also find Vermont Country Store and Lowell Lake State Park 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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