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Check prices for these dates

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23 Sept - 24 Sept
Tomorrow
24 Sept - 25 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Kirsty
Rp2.843.556
Rp3.099.476 total
includes taxes & fees
18 Oct - 19 Oct
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
John
Rp3.727.899
Rp4.063.410 total
includes taxes & fees
24 Sept - 25 Sept
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
Rp3.196.576
Rp3.516.232 total
includes taxes & fees
21 Oct - 22 Oct
Best Western Springfield Hotel

4. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
John
Rp2.457.532
Rp2.703.285 total
includes taxes & fees
29 Sept - 30 Sept
Comfort Inn & Suites Brattleboro I-91

5. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
Michael
Rp3.435.726
Rp3.744.942 total
includes taxes & fees
24 Sept - 25 Sept
Harvest Barn Inn

6. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
Rp2.569.037
Rp2.928.702 total
includes taxes & fees
18 Oct - 19 Oct
Pointe at Castle Hill Resort

7. The Hartness House

The Hartness House
Springfield
United States
Dan
Rp3.693.940
Rp4.063.334 total
includes taxes & fees
28 Sept - 29 Sept
The Hartness House

8. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Victoria
Rp3.276.709
Rp3.555.301 total
includes taxes & fees
22 Oct - 23 Oct
The Common Man Inn & Restaurant

9. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
David
Rp2.498.580
Rp2.710.960 total
includes taxes & fees
24 Sept - 25 Sept
Keene Elm City Hotel, an Ascend Collection Hotel

10. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
Rp1.783.986
Rp2.042.664 total
includes taxes & fees
24 Sept - 25 Sept
The Upper Pass Lodge at Magic Mountain

11. The Putney Inn

The Putney Inn
Putney
United States
JANE
Rp1.947.568
Rp2.142.324 total
includes taxes & fees
27 Sept - 28 Sept
The Putney Inn

12. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
Rp2.664.716
Rp2.891.306 total
includes taxes & fees
24 Sept - 25 Sept
Best Western Plus Keene Hotel

13. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Francesca
Rp2.443.312
Rp2.687.643 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn Brattleboro

14. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
EDWARD S
Rp2.146.080
Rp2.328.497 total
includes taxes & fees
18 Oct - 19 Oct
Claremont Motor Lodge

15. Black Mountain Inn

Black Mountain Inn
Brattleboro
United States
Denise
Rp2.716.580
Rp2.988.238 total
includes taxes & fees
27 Sept - 28 Sept
Black Mountain Inn

16. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
VINCENT JOEL
Rp1.528.001
Rp1.680.801 total
includes taxes & fees
24 Sept - 25 Sept
The Covered Bridge Inn

17. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Daniel
Rp3.487.380
Rp3.836.118 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG

18. Royal Inn Claremont

Royal Inn Claremont
Claremont
United States
Eva
Rp2.141.618
Rp2.323.656 total
includes taxes & fees
30 Sept - 1 Oct
Royal Inn Claremont

19. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
sheri
Rp2.859.652
Rp3.102.722 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn & Suites Keene

20. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Shannon
Rp3.198.911
Rp3.781.929 total
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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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

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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
Ann 2-night trip
Posted 10 hours ago
Woodstock Inn & Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice stay and nice rooms."
Nicole 1-night trip
Posted 14 hours ago
Pointe at Castle Hill Resort
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Wonderful relaxing stay!"
Rosemary 2-night trip
Posted 17 hours ago
Hampton Inn and Suites Manchester
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

10/10 Excellent
"Our group of four ladies had an excellent time at the historic Stone Hearth Inn. We stayed in a lovely room with 4 single beds. They were very accommodating, including a late check-in and breakfast. Breakfast included homemade bread and other fresh food in a beautiful setting overlooking the lush backyard. It is a family run operation. We were checked in and served breakfast by Vicki, because her son Edward , daughter Georgia and son-in-law Conner were all working at the local Chester Festival. We really enjoyed meeting and getting to know Vicky. We did sample fresh made donuts and pretzels at the festival. They were amazing! The room was clean and comfortable. Unfortunately, we did not get to eat in the restaurant because it was closed during the festival. We are all certain that the food there would’ve been excellent as both Georgia and Connor are master chefs. All four of us ladies highly recommend this gem in beautiful Chester, Vermont. In any season, it’s a beautiful, relaxing place to stay while exploring the things available nearby, including historic, towns and buildings, covered bridges, hiking, skiing, and great food."
Alison 2-night trip
Posted 20 hours ago
Stone Hearth Inn and Eatery
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Nice"
Thomas 3-night trip
Posted 1 day ago
Jackson Gore Village, A Vail Resorts Property
Latchis Hotel

Latchis Hotel

10/10 Excellent
"WE enjoyed the architecture of the whole complex - reception coffee lounge (Hot Drinks day and night as a compliment). Parking was right there. Center of town. The staff helped us when we needed to extend at the special rate. It attracts fun guests. It is a special place - not the run of the mill franchise. The linen is first class, nice thick towels. The room had a microwave and a refrig, plus the record player theme is another theme for folks who appreciate the vinyl era. Remember - Art Deco Era - not modern era."
Kris 6-night trip
Posted 2 days ago
Latchis Hotel
The Jackson

The Jackson

8/10 Good
"The Hostess at the wine and cheese hour was very kind and helpful. That was the only time we saw anyone! The house is divided into separate areas and we were in the oldest part. The bed was comfortable, bathroom nice, amenities nice but wouldn’t book again because of the very narrow and steep stairs. My husband is 80, hauling luggage up those kind of stairs is dangerous. That would be the only reason not to return."
Robin 1-night trip
Posted 2 days ago
The Jackson
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"The pool was not available due to repair. The parking was limited (we had to walk up/down the hill to overflow parking). The faucet in our room made machine gun noise. The room was pretty big and clean. Deli was good. The restaurant bartender was very helpful. The shuttle bus service was great."
Hisayo 2-night trip
Posted 3 days ago
Grand Summit Resort, A Vail Resorts Property
On The River Inn

On The River Inn

8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Marcia 2-night trip
Posted 4 days ago
On The River Inn

More cheap stays in Chester

Claremont Motor Lodge

Claremont Motor Lodge

16 Beauregard St Claremont NH
Rp2.146.080
Rp2.328.497 total
18 Oct - 19 Oct
includes taxes & fees
Claremont Motor Lodge
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
Rp2.148.762
Rp2.363.639 total
27 Sept - 28 Sept
includes taxes & fees
The Manchester View
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
Rp2.274.308
Rp2.501.739 total
28 Sept - 29 Sept
includes taxes & fees
8.6/10 Excellent! (989 reviews)
Latchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
Rp2.443.312
Rp2.687.643 total
29 Sept - 30 Sept
includes taxes & fees
8.2/10 Very good! (1,000 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
Rp2.498.580
Rp2.710.960 total
24 Sept - 25 Sept
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
Rp3.047.791
Rp3.352.570 total
22 Oct - 23 Oct
includes taxes & fees
9.6/10 Exceptional! (1,000 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. Stone Hearth Inn and Eatery is another good choice for your visit. 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 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: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. The Manchester View and Pointe at Castle Hill Resort 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 66 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. 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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