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11 Aug - 12 Aug
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12 Aug - 13 Aug
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14 Aug - 16 Aug
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21 Aug - 23 Aug

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Kirsty
Rp2.467.945
Rp2.690.060 total
includes taxes & fees
1 Sept - 2 Sept
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
Olena
Rp3.708.682
Rp4.042.464 total
includes taxes & fees
19 Aug - 20 Aug
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
Rp3.180.098
Rp3.498.108 total
includes taxes & fees
20 Aug - 21 Aug
Best Western Springfield Hotel

4. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
Canada
Natalie
Rp3.087.239
Rp3.365.090 total
includes taxes & fees
16 Aug - 17 Aug
Harvest Barn Inn

5. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Denis
Rp2.395.160
Rp2.598.776 total
includes taxes & fees
7 Sept - 8 Sept
The Common Man Inn & Restaurant

6. The Hartness House

The Hartness House
Springfield
United States
Dan
Rp3.340.007
Rp3.674.008 total
includes taxes & fees
18 Aug - 19 Aug
The Hartness House

7. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
Shane
Rp1.953.050
Rp2.119.060 total
includes taxes & fees
17 Aug - 18 Aug
Claremont Motor Lodge

8. The Putney Inn

The Putney Inn
Putney
United States
Robert
Rp2.197.181
Rp2.416.988 total
includes taxes & fees
13 Aug - 14 Aug
The Putney Inn

9. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Bonnie
Rp2.397.280
Rp2.637.009 total
includes taxes & fees
6 Sept - 7 Sept
Comfort Inn & Suites Brattleboro I-91

10. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Ramica
Rp2.284.636
Rp2.478.760 total
includes taxes & fees
10 Sept - 11 Sept
Keene Elm City Hotel, an Ascend Collection Hotel

11. Bromley View Inn

Bromley View Inn
Bondville
United States
Josh
Rp1.357.547
Rp1.493.196 total
includes taxes & fees
16 Aug - 17 Aug
Bromley View Inn

12. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Helen
Rp2.645.495
Rp2.870.451 total
includes taxes & fees
3 Sept - 4 Sept
Best Western Plus Keene Hotel

13. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Greg
Rp2.096.155
Rp2.305.771 total
includes taxes & fees
8 Sept - 9 Sept
Hampton Inn Brattleboro

14. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
Michael
Rp1.463.900
Rp1.588.331 total
includes taxes & fees
1 Sept - 2 Sept
Days Inn by Wyndham Keene NH

15. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Stephen
Rp2.823.045
Rp3.218.272 total
includes taxes & fees
16 Aug - 17 Aug
Pointe at Castle Hill Resort

16. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
VINCENT JOEL
Rp1.374.947
Rp1.512.371 total
includes taxes & fees
17 Aug - 18 Aug
The Covered Bridge Inn

17. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
United States
Patricia
Rp2.751.670
Rp3.026.837 total
includes taxes & fees
20 Aug - 21 Aug
Hampton Inn and Suites Manchester

18. Black Mountain Inn

Black Mountain Inn
Brattleboro
United States
Robert
Rp2.696.985
Rp2.966.684 total
includes taxes & fees
13 Aug - 14 Aug
Black Mountain Inn

19. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Bradley
Rp1.625.647
Rp1.804.467 total
includes taxes & fees
1 Sept - 2 Sept
The Upper Pass Lodge at Magic Mountain

20. Colonial Motel

Colonial Motel
Brattleboro
United States
James
Rp1.326.298
Rp1.458.926 total
includes taxes & fees
16 Aug - 17 Aug
Colonial Motel
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Where to stay in Chester

Find the best Chester areas 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

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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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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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

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"Cool little property….very clean & quiet. There isn’t anything around it but that wasn’t an issue for us."
Kim 3-night trip
Posted 1 hour ago
Sleep Woodstock Motel
The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Nice place to stay was major construction going on which didn't bother us too much but might have been nice to be aware beforehand. We had a lovely room on the second floor."
Lynette 1-night trip
Posted 7 hours ago
The Shire Woodstock
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Everything was very clean and very well taken care of. The bed was very comfortable the place where I think maybe the stay was lacking was the breakfast, not very exciting. It was adequate and well stocked. I do like that. There was coffee available 24 hours."
Margaret 2-night trip
Posted 7 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The breakfast was great. The staff was very friendly."
Greg 2-night trip
Posted 1 day ago
Hampton Inn Brattleboro
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Everything ouais, Perfect"
Daniel 1-night trip
Posted 2 days ago
Hampton Inn and Suites Manchester
Latchis Hotel

Latchis Hotel

8/10 Good
"In an old Theater building. Definitely has character and cool features. We arrived too late for the movies, but still fun. In central Brattleboro which has some interesting shops, but is suffering from homelessnes and mental illness/drug use. Didnt really feel unsafe and we walked a few blocks to a fun restaurant with good food & karioke. Person at desk was lovely and helpful. Room was ok- a little dated and could be cleaner."
Jonathan 1-night trip
Posted 2 days ago
Latchis Hotel
The Jackson

The Jackson

10/10 Excellent
"Wonderful place to rest and enjoy the beautiful town and scenery"
Geneva 1-night trip
Posted 2 days ago
The Jackson
Colonial Motel

Colonial Motel

8/10 Good
"Kind personnel, large green area. Breakfast is too basic though."
Alex 2-night trip
Posted 4 days ago
Colonial Motel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Perfect"
zhuang 4-night trip
Posted 4 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
Rp1.463.900
Rp1.588.331 total
1 Sept - 2 Sept
includes taxes & fees
7/10 Good! (1,005 reviews)
Days Inn by Wyndham Keene NH
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
Rp2.096.155
Rp2.305.771 total
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
Rp2.150.041
Rp2.365.045 total
23 Aug - 24 Aug
includes taxes & fees
Latchis Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
Rp2.284.636
Rp2.478.760 total
10 Sept - 11 Sept
includes taxes & fees
8.6/10 Excellent! (1,000 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
Rp2.397.280
Rp2.637.009 total
6 Sept - 7 Sept
includes taxes & fees
Comfort Inn & Suites Brattleboro I-91
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
Rp2.751.670
Rp3.026.837 total
20 Aug - 21 Aug
includes taxes & fees
9.6/10 Exceptional! (1,014 reviews)
Hampton Inn and Suites Manchester

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventure: Chester is perfect for ski enthusiasts and offers various outdoor activities amidst stunning natural scenery.
  • Cultural Experiences: Engage with local culture through agricultural exhibits, art galleries, and history museums.
  • Charming Accommodations: Enjoy a range of lodging options, from cosy bed & breakfasts to unique agritourism properties.
  • Picturesque Scenery: Experience the vibrant autumn colours and beautiful landscapes that enhance your visit.
  • Warm Hospitality: Delight in the friendly atmosphere and welcoming locals that make Chester a memorable destination.

Find great hotels near Chester

Discover the charming lodging options in Chester, Vermont, where a variety of accommodations await to suit every traveller's needs. Whether you prefer a cosy bed & breakfast or unique agritourism properties, you'll find affordable stays equipped with air conditioning and family-friendly amenities. Enjoy a delightful American breakfast and consider spacious suites for a comfortable retreat after your adventures in this picturesque locale.

  • The Upper Pass Lodge at Magic Mountain: Embrace the spirit of adventure at The Upper Pass Lodge at Magic Mountain, a pet-friendly motel located a mere 16.1km from Chester. This lodge is perfect for those seeking an action-packed getaway, offering a variety of exciting activities such as snowshoeing, ziplining, and fishing. Guests can enjoy the thrill of adventure sports right on their doorstep, making it an ideal choice for outdoor enthusiasts. The lodge also welcomes pets, providing amenities that ensure a comfortable stay for both you and your furry companions.
  • Main and Mountain Bar & Motel: Situated 17.7km from Chester, Main and Mountain Bar & Motel is a haven for adventure seekers. This motel features a laid-back atmosphere complemented by an array of recreational activities, including mountain biking, kayaking, and swimming. With its proximity to stunning natural landscapes, guests can easily explore the great outdoors and return to a welcoming environment. The combination of adventure and comfort makes this motel a perfect choice for those looking to immerse themselves in Vermont's natural beauty.
  • Castle Hill Resort And Spa: Experience a luxurious retreat at Castle Hill Resort And Spa, located just 14.5km from Chester. This 3.5-star hotel caters to travellers seeking both adventure and opulence. Guests can indulge in a variety of activities such as snowboarding, kayaking, and mountain biking, all while enjoying the resort's upscale amenities. With a focus on providing a high-end experience, Castle Hill combines relaxation and excitement, making it an exceptional choice for those wishing to unwind after a day of exploration.

Where to stay near Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation, making it an ideal destination for travellers seeking both excitement and tranquillity. Surrounded by charming towns and stunning natural scenery, visitors can enjoy outdoor activities like skiing and exploring historical sites. The vibrant autumn colours create a picturesque backdrop, inviting you to celebrate nature's beauty while experiencing the warm hospitality of the locals. Whether you're on a budget or seeking luxury, Chester has something for everyone.

  • Ludlow: Located approximately 17.7km from Chester, Ludlow is a vibrant city that attracts visitors year-round, peaking during the winter months from December to February. Renowned for its exceptional skiing and adventurous sports, Ludlow is a haven for outdoor enthusiasts. The nearby ski resorts and fields provide thrilling experiences, while the stunning landscapes of lakes, mountains, and valleys create a picturesque backdrop for exploration. Whether you're hitting the slopes or enjoying a quiet moment by the lake, Ludlow promises an exhilarating travel experience.
  • Springfield: Just 9.7km from Chester, Springfield is a charming city with a diverse array of attractions that draw visitors throughout the year. Peak seasons occur in February, July, and September, making it an appealing destination for adventure seekers. Springfield is known for its excellent skiing facilities and access to national state parks, offering a perfect blend of outdoor activities. The scenic beauty of the surrounding lakes and mountains adds to its allure, making Springfield a delightful spot for those seeking a mix of excitement and natural beauty.
  • Grafton: Situated a mere 9.7km from Chester, Grafton is a quaint city that offers a unique blend of outdoor adventure and serene landscapes. With peak visitor numbers in July and September to October, Grafton is ideal for those looking to enjoy skiing and outdoor activities amidst its stunning valleys and mountains. The welcoming atmosphere and beautiful surroundings make Grafton a fantastic choice for a peaceful retreat, where you can savour the beauty of nature while indulging in thrilling sports experiences.

Things to do near Chester

Chester, Vermont, offers a delightful blend of outdoor adventure and cultural attractions. Visitors can enjoy skiing at local resorts and engaging in various sports activities. Additionally, the town features agricultural exhibits, art galleries, and animal shows, making it perfect for day trips. Whether you're seeking adrenaline or a taste of local culture, Chester promises a memorable experience for all.

Shopping

In Chester, visit the Vermont Country Store and My Minds Design, both located 9.7km away, for charming gifts and souvenirs. If you're up for a drive, the West River Farmers Market, 17.7km away, offers a delightful selection of local produce and crafts in a vibrant atmosphere.

Recreation

At Crown Point Golf Course, enjoy a leisurely round of golf amidst picturesque landscapes, just 12.9km from Chester. Fox Run Golf Course, located 19.3km away, offers a vibrant sports atmosphere. For relaxation, visit The Ice House Ice Skating, 20.9km from Chester, where wellness and serenity await.

Adventure

Morningside Flight Park offers a breathtaking scenic flight experience, 19.3km from Chester, where you'll enjoy stunning views and a rush of adventure in the skies. For winter sports enthusiasts, Okemo Mountain Resort, located 17.7km away, provides excellent skiing opportunities amidst exhilarating snow-covered landscapes.

Nightlife

In Chester, the Weston Playhouse offers a charming theatre experience just 16.1km away, perfect for romance and culture. For an adventurous night, head to Maple Lanes, an arcadeAdventureZone 22.5km away, or try the Timber Ripper Mountain Coaster, located 20.9km from Chester for an exhilarating ride.

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

Booking tips and Expedia advantages for Chester

When planning your visit to Chester, Vermont, consider travelling in the cheaper months of April to May and November, with Tuesdays being the most affordable days to stay. Use Expedia’s search tool to filter for your budget and preferred accommodation, and sort by price to find the best deals. Look for package options that combine flights and hotels for additional savings. To explore the area on a budget, seek out free local activities and utilise public transport whenever possible to keep costs down.

  • 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. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save money by combining your hotel reservation in Chester with your flights and activities through an Expedia package.

Find the best attractions near Chester

Chester, Vermont, is perfect for ski enthusiasts and adventure seekers, offering a variety of outdoor activities and cultural experiences. Visitors can explore local parks, national and state parks, and history museums, making it an ideal destination for families and those interested in the region's heritage. Whether you're keen on sports or simply wish to enjoy the natural beauty, Chester has something for everyone.

  • Vermont Museum of Mining and Minerals: Located 9.7km from Chester, this museum offers a fascinating glimpse into the region's mining history. Visitors can explore various exhibits showcasing minerals and mining artefacts, making it an enriching experience for families and culture enthusiasts alike.
  • Lowell Lake State Park: Situated 14.5km away, this national park is a haven for outdoor lovers. With its stunning scenery and numerous trails, visitors can enjoy hiking, kayaking, and picnicking amidst breathtaking natural beauty, perfect for adventure seekers.
  • Grafton Historical Society: Just 9.7km from Chester, this history museum presents the rich cultural heritage of the area. Through engaging exhibits and local artefacts, visitors can delve into the history of Grafton and its significance in Vermont.

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 visit to Chester, Vermont, you have several nearby airports to consider. Lebanon Municipal Airport (LEB) is 46.7km away, with hotels like the Windsor Mansion Inn, Residence Inn by Marriott Hanover Lebanon, and Sunset Motor Inn, all offering convenient access. Rutland Southern Vermont Regional Airport (RUT) is 40.2km away, featuring options such as Cortina Inn and Killington Mountain Lodge, which provide shuttle services. Additionally, Hartness State Airport (VSF) is just 11.3km from Chester, with nearby accommodations including the 4-star Inn at Weathersfield and Castle Hill Resort And Spa. Each airport ensures a variety of transport options to facilitate your journey.

Frequently asked questions

Where is the best place to stay in Chester?
Based on our traveller 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 stay in the area are Woodstock Inn & Resort and Keene Elm City Hotel, an Ascend Collection Hotel. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Okemo Mountain Lodging by Vail Resorts: This holiday home rental outside Chester is in the mountains and offers cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. 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 if cancelled prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What's the best dog-friendly accommodation option in Chester?
Motel in the Meadow is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Chester.
What are some accommodation options with pools in Chester?
Woodstock Inn & Resort: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. Keene Elm City Hotel, an Ascend Collection Hotel and Kimpton Taconic Hotel by IHG are two additional hotels that feature an on-site pool. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors to Chester will definitely enjoy the skiing, cafes and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 62 hotels and other accommodation options to choose from. Find out more about Chester.
What should I do while I'm visiting Chester?
A couple of favourite 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. Take a look at what more there is 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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.

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