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Chester Hotels

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Aug 24 - Aug 25
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Aug 25 - Aug 26
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Aug 28 - Aug 30
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Our top choices for Chester hotels

Reserve now, pay later
Pet friendly
Motel
Hotel
Bed & breakfast

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Kirsty
P8,578
P9,350 total
includes taxes & fees
Aug 31 - Sep 1
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
Olena
P12,891
P14,051 total
includes taxes & fees
Aug 25 - Aug 26
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
P9,943
P10,937 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Springfield Hotel

4. The Hartness House

The Hartness House
Springfield
United States
Dan
P10,937
P12,030 total
includes taxes & fees
Aug 26 - Aug 27
The Hartness House

5. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Stephen
P9,387
P10,701 total
includes taxes & fees
Aug 25 - Aug 26
Pointe at Castle Hill Resort

6. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
Michael
P10,731
P11,696 total
includes taxes & fees
Aug 31 - Sep 1
Harvest Barn Inn

7. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Denis
P8,276
P8,979 total
includes taxes & fees
Sep 7 - Sep 8
The Common Man Inn & Restaurant

8. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
Kristina
P9,008
P9,909 total
includes taxes & fees
Aug 31 - Sep 1
Main and Mountain Bar & Motel

9. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
Sergio
P6,788
P7,365 total
includes taxes & fees
Aug 25 - Aug 26
Claremont Motor Lodge

10. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Mirco
P16,607
P18,102 total
includes taxes & fees
Aug 27 - Aug 28
Castle Hill Resort And Spa

11. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Gene
P8,578
P10,368 total
includes taxes & fees
Aug 25 - Aug 26
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

12. Royal Inn Claremont

Royal Inn Claremont
Claremont
United States
Eva
P6,110
P6,629 total
includes taxes & fees
Aug 27 - Aug 28
Royal Inn Claremont

13. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
P9,195
P10,115 total
includes taxes & fees
Aug 26 - Aug 27
Blue Gentian Lodge at Magic Mountain

14. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
P12,158
P15,523 total
includes taxes & fees
Aug 25 - Aug 26
The Inn at Weathersfield

15. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
United States
Patricia
P9,433
P10,376 total
includes taxes & fees
Aug 30 - Aug 31
Hampton Inn and Suites Manchester

16. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
United States
Luis
P8,054
P9,745 total
includes taxes & fees
Sep 2 - Sep 3
The Black Bear Lodge at Stratton Mountain Resort

17. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
P5,650
P6,272 total
includes taxes & fees
Sep 1 - Sep 2
The Upper Pass Lodge at Magic Mountain

18. The Putney Inn

The Putney Inn
Putney
United States
JANE
P6,721
P7,393 total
includes taxes & fees
Sep 1 - Sep 2
The Putney Inn

19. Bromley View Inn

Bromley View Inn
Bondville
Canada
William
P4,719
P5,190 total
includes taxes & fees
Aug 25 - Aug 26
Bromley View Inn

20. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Morgan
P7,992
P8,791 total
includes taxes & fees
Aug 31 - Sep 1
Comfort Inn & Suites Brattleboro I-91
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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

Bonnie's Bundles Dolls

7.6/10 (4 reviews)
This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.
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DaVallia Art & Accents

10.0/10 (2 reviews)
This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.
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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.

See all hotels in Chester
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Good location near everything you need rooms have river views"
Paul 1-night trip
Posted less than an hour ago
The Shire Woodstock
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Great place! A little expensive"
Laurece 3-night trip
Posted 5 hours ago
Hampton Inn and Suites Manchester
On The River Inn

On The River Inn

8/10 Good
"Everything about the Inn was great. There was a major price discrepancy between the 3rd party booking site I used (Expedia) and what was actually charged but I have yet to get to the bottom of the issue."
Joe 3-night trip
Posted 6 hours ago
On The River Inn
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"The room was clean and stocked with the amenities expected, including a fridge and a microwave. Staff was very helpful and kind on check in. Breakfast was a standard continental. Not the best food but there was an array of options."
Samantha 1-night trip
Posted 9 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Colonial Motel

Colonial Motel

8/10 Good
"X"
Steven 1-night trip
Posted 14 hours ago
Colonial Motel
Claremont Motor Lodge

Claremont Motor Lodge

8/10 Good
"Sorry. I do not wish to write a review."
Stephenson 3-night trip
Posted 2 days ago
Claremont Motor Lodge
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."
Chris 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Latchis Hotel

Latchis Hotel

8/10 Good
"The art deco building is gorgeous. I applaud the non-profit organization that saved, renovated and maintains this exceptional building. I very much appreciated the original bathroom fixtures. The hotel really gives you a taste of what it might have been like to travel back in the 1930-40s. On the downside, my experience was not the best: When I arrived, the front desk lady said something like: "I'll be right with you". Two minutes later, she came to the front desk joking about having problems with her Emails. Not acceptable! You should pause your Email activity when someone is waiting in the lobby. My wife and I were looking forward to a drink at the hotel bar. The website indicated that the bar was open, and a note on the door confirmed. There was nobody there. Money and a lady's purse were spread out on the bar. We were told at the front desk that the people running the bar for them decided not to open that evening. Not acceptable. The next morning I took a lukewarm shower, as it took about ten minutes for the water to become warm enough, By then I was done and my feet were in about 5" of dirty water because the drain was clogged. We were also told that if we did not turn in our brass key, they would charge us $75 to replace it. When walked down to the lobby, there was a sign stating that front desk duty started at 9:00."
Denis 1-night trip
Posted 3 days ago
Latchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Staff were extremely friendly. The whole place was clean. Hit tub was really a whirlpool..movement but no bubbles. So nice and warm though. Great stay!!"
Deborah 2-night trip
Posted 3 days ago
Hampton Inn Brattleboro

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
P5,981
P6,489 total
Sep 16 - Sep 17
includes taxes & fees
7/10 Good! (1,004 reviews)
Days Inn by Wyndham Keene NH
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
P6,836
P7,520 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (964 reviews)
Latchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
P7,022
P7,724 total
Sep 8 - Sep 9
includes taxes & fees
8.2/10 Very Good! (1,015 reviews)
Hampton Inn Brattleboro
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
P7,406
P8,035 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
P7,992
P8,791 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (849 reviews)
Comfort Inn & Suites Brattleboro I-91
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
P9,433
P10,376 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (1,013 reviews)
Hampton Inn and Suites Manchester

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?
Located 25.2 mi (40.5 km) from the heart of Chester, Woodstock Inn & Resort is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Kimpton Taconic Hotel by IHG and Holiday Inn Club Vacations Mount Ascutney Resort by IHG. 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: Features a seasonal outdoor pool, an indoor pool, and 4 restaurants. Kimpton Taconic Hotel by IHG and Keene Elm City Hotel, an Ascend Collection Hotel 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?
A couple of favorite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. 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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