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Oct 8 - Oct 9
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Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
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Oct 16 - Oct 18

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
kris
P9,352
P10,193 total
includes taxes & fees
Nov 1 - Nov 2
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
John
P17,701
P19,294 total
includes taxes & fees
Oct 12 - Oct 13
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
P9,547
P10,502 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Springfield Hotel

4. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
P9,564
P10,903 total
includes taxes & fees
Oct 28 - Oct 29
Pointe at Castle Hill Resort

5. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
P14,229
P17,819 total
includes taxes & fees
Nov 4 - Nov 5
The Inn at Weathersfield

6. The Hartness House

The Hartness House
Springfield
United States
Elizabeth
P12,580
P13,838 total
includes taxes & fees
Nov 1 - Nov 2
The Hartness House

7. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
United States
Rosemary
P9,549
P10,504 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn and Suites Manchester

8. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
gail
P9,549
P10,409 total
includes taxes & fees
Nov 1 - Nov 2
Harvest Barn Inn

9. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Jessica
P11,308
P13,739 total
includes taxes & fees
Oct 26 - Oct 27
Jackson Gore Village, A Vail Resorts Property

10. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
P6,274
P7,184 total
includes taxes & fees
Oct 12 - Oct 13
The Upper Pass Lodge at Magic Mountain

11. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
Canada
Paul
P8,724
P9,596 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Hotel & Suites Brattleboro by IHG

12. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
Canada
Bruce
P8,134
P8,826 total
includes taxes & fees
Nov 1 - Nov 2
The Common Man Inn & Restaurant

13. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
P16,890
P18,410 total
includes taxes & fees
Oct 19 - Oct 20
Castle Hill Resort And Spa

14. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
P6,943
P7,638 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Brattleboro I-91

15. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
Caroline
P10,883
P11,808 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield Inn & Suites by Marriott Keene Downtown

16. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
Patricia
P14,912
P16,404 total
includes taxes & fees
Oct 12 - Oct 13
Main and Mountain Bar & Motel

17. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
P9,352
P10,287 total
includes taxes & fees
Nov 3 - Nov 4
Blue Gentian Lodge at Magic Mountain

18. The Manchester View

The Manchester View
Manchester Center
United States
Isaac
P5,296
P5,825 total
includes taxes & fees
Nov 3 - Nov 4
The Manchester View

19. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Rebecca
P8,803
P9,551 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Keene

20. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Francesca
P7,202
P7,922 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Brattleboro
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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, Bonnie's Bundles Dolls and DaVallia Art & Accents 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

Fullerton Inn

Fullerton Inn

10/10 Excellent
"Room was small but clean. Staff very helpful and welcoming. Parking available right outside the hotel. There was a fridge close to reception for guest use. Lovely location in a typical New England town with lots of interesting shops. Bar offered a good selection of draft beers. Continental breakfast had very little left at 9.00am - probably our own fault for leaving it so late. Would definitely return."
Anita 1-night trip
Posted 5 hours ago
Fullerton Inn
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good
"Nice hotel. Dated, but nice. Internet speed and connectivity is terrible. Good launching point for the Stowe area attractions to allow access off of back routes to avoid traffic. No breakfast."
Steven 1-night trip
Posted 10 hours ago
The Black Bear Lodge at Stratton Mountain Resort
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

8/10 Good
"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 nights because of the difficulty of the stairs… It was however nice if no handicaps"
Dorothy 2-night trip
Posted 21 hours ago
Stone Hearth Inn and Eatery
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Lovely feel to the hotel with friendly staff. Room was comfortable and location is excellent. Love Woodstock as a destination. I am never the biggest fan of breakfast, but really enjoyed it for once"
patrick 3-night trip
Posted 1 day ago
Woodstock Inn & Resort
Latchis Hotel

Latchis Hotel

8/10 Good
"We enjoyed our stay at the historic Latchis Hotel. You really get the feeling of stepping back in time. The staff were very helpful and provided recommendations on places to eat besides just checking us in. The room was fine and the working record player with records was a nice touch. Parking is about a half block away behind the hotel. Make sure you see the historic Latchis Theater’s main room. It is really amazing and will definitely take you back in time."
Jaren 1-night trip
Posted 1 day ago
Latchis Hotel
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

8/10 Good
"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received our check-in information, we were given a room on the 2nd floor. If we only had to carry backpacks, it might have been fine. However, we had large cases, so it was difficult to drag them up the stairs. Also, if you are an above average size person, know that these rooms are small spaces. The bathroom is barely big enough to turn around in and the shower is tiny."
KERRY 1-night trip
Posted 2 days ago
Hideaway Inn Mt. Snow
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"Allen in the restaurant is great."
Bettina 1-night trip
Posted 2 days ago
Grand Summit Resort, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

8/10 Good
"Everything about this property was exceptional, EXCEPT the bed. We had an amazing time, enjoyed the lift to view fall colors & mountain coaster. But we had a miserable experience sleeping. The beds are like rock. I know it's the granite state, but get some toppers!"
Pamela 4-night trip
Posted 2 days ago
Jackson Gore Village, A Vail Resorts Property
On The River Inn

On The River Inn

10/10 Excellent
"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."
VS 4-night trip
Posted 2 days ago
On The River Inn

More cheap stays in Chester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
P5,282
P5,810 total
Oct 25 - Oct 26
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
The Putney Inn
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
P5,296
P5,825 total
Nov 3 - Nov 4
includes taxes & fees
9.4/10 Exceptional! (923 reviews)
The Manchester View
Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
P5,823
P7,095 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (699 reviews)
Aspen At Manchester
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
P7,469
P8,104 total
Nov 2 - Nov 3
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
P8,897
P9,786 total
Nov 1 - Nov 2
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Latchis Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
P9,549
P10,504 total
Nov 1 - Nov 2
includes taxes & fees
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?
Based on our traveler 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 stay. 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. Aspen At Manchester and The Manchester View 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 67 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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