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Chester Hotels

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (466 reviews)
"Stayed there 7yrs.ago and had another great experience this time, Cloe our waitress was excellent and made our dining alot of fun."
United States
Tim
The price is P8,133
P8,865 total
includes taxes & fees
Nov 10 - Nov 11
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (130 reviews)
"Wonderful staff and restaurant"
United States
John
The price is P13,170
P14,355 total
includes taxes & fees
Nov 16 - Nov 17
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (894 reviews)
"Everything was excellent!"
United States
Dominick
The price is P9,590
P10,549 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Springfield Hotel

4. The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very good, (366 reviews)
"very historic place, beautiful and elegant"
United States
Zhenchun
The price is P11,867
P13,054 total
includes taxes & fees
Nov 10 - Nov 11
The Hartness House

5. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,001 reviews)
"Amazing rooms, sweet staff, great amenities - gorgeous location!"
United States
Cristian
The price is P9,187
P10,473 total
includes taxes & fees
Nov 15 - Nov 16
Pointe at Castle Hill Resort

6. The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (83 reviews)
"Such a nice and kind family of owners. Breakfast was delicious, as well as dinner the previous night in their restaurant. It’s a very rustic Inn, full of history and charm. We would love to return in the near future."
United States
Dorrie
The price is P13,045
P16,539 total
includes taxes & fees
Nov 29 - Nov 30
The Inn at Weathersfield

7. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1,000 reviews)
"Wonderful relaxing stay!"
United States
Rosemary
The price is P8,092
P8,901 total
includes taxes & fees
Nov 29 - Nov 30
Hampton Inn and Suites Manchester

8. Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (127 reviews)
"I promise, especially if you’re staying in the condo buildings you will love it"
United States
Brandon
The price is P11,292
P12,308 total
includes taxes & fees
Nov 10 - Nov 11
Castle Hill Resort And Spa

9. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (448 reviews)
"We enjoyed our stay here."
United States
Anna
The price is P8,171
P8,866 total
includes taxes & fees
Nov 12 - Nov 13
The Common Man Inn & Restaurant

10. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (296 reviews)
"Staff was excellent and river views were amazing"
United States
John
The price is P10,245
P11,167 total
includes taxes & fees
Nov 27 - Nov 28
Harvest Barn Inn

11. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
2.5 star property
Londonderry
8.2 out of 10, Very good, (714 reviews)
"Beds and bedding were super comfy but the room itself was rather small and dated."
United States
Lynne
The price is P5,296
P6,064 total
includes taxes & fees
Nov 16 - Nov 17
The Upper Pass Lodge at Magic Mountain

12. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,002 reviews)
"Stayed one night. Staff was very friendly. Clean rooms, easy parking, nice breakfast."
United States
Timothy
The price is P8,764
P9,640 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Hotel & Suites Brattleboro by IHG

13. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (899 reviews)
"Very nice staff and enjoyed my stay."
United States
Charlene
The price is P7,080
P7,788 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites Brattleboro I-91

14. The Landgrove

The Landgrove
3.5 star property
Londonderry
9.4 out of 10, Exceptional, (15 reviews)
"Had a great stay, room was set up with a very comfortable Home feel, not a sterile Hotel."
United States
Alan
The price is P10,550
P11,499 total
includes taxes & fees
Nov 16 - Nov 17
The Landgrove

15. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (128 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is P9,394
P10,334 total
includes taxes & fees
Nov 9 - Nov 10
Blue Gentian Lodge at Magic Mountain

16. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (611 reviews)
"Room was clean, staff was polite, parking was easy."
United States
Katie
The price is P7,566
P8,209 total
includes taxes & fees
Nov 9 - Nov 10
Claremont Motor Lodge

17. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
3.0 star property
Jackson Gore Base Area
8.6 out of 10, Excellent, (973 reviews)
"Excellent place to stay!! The breakfas it good, bed comfortables and the view is nice."
United States
Adriana
The price is P11,644
P14,147 total
includes taxes & fees
Nov 18 - Nov 19
Jackson Gore Village, A Vail Resorts Property

18. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (898 reviews)
"Great staff and very good food at the resturant. Will come back in the future!"
United States
Richard
The price is P8,125
P9,897 total
includes taxes & fees
Nov 9 - Nov 10
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

19. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,003 reviews)
"Excellent stay"
United States
Lisa
The price is P8,385
P9,098 total
includes taxes & fees
Nov 9 - Nov 10
Keene Elm City Hotel, an Ascend Collection Hotel

20. The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (966 reviews)
"Great breakfast as well as a lovely property!"
United States
Pauline
The price is P7,150
P7,865 total
includes taxes & fees
Nov 15 - Nov 16
The Manchester View
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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

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.

A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

More cheap stays in Chester

Find out more about Chester

Top reasons to visit Chester

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

Find great hotels near Chester

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

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

Where to stay near Chester

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

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

Things to do near Chester

Chester, Vermont, is a delightful destination for those seeking outdoor adventures and winter sports. Visitors can indulge in skiing at nearby resorts and explore various ski fields. Additionally, the town boasts quirky shops that offer a unique shopping experience, making it an ideal spot for a memorable holiday filled with both excitement and charm.

Shopping

For a delightful shopping experience in Chester, visit the Vermont Country Store and My Minds Design, both located 9.7km away. If you're up for a drive, head to the West River Farmers Market, situated 17.7km from Chester, offering a vibrant local atmosphere and unique finds.

Recreation

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

Adventure

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

Nightlife

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

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

Booking tips and Expedia advantages for Chester

For a budget-friendly trip to Chester, Vermont, consider visiting during the cheaper months of April to May and November, avoiding the peak seasons of January to February and October. Book your stay on a Tuesday for the best rates and use Expedia's search tool to filter by budget and eco-friendly accommodations. Combine hotel, flight, and activity bookings for additional savings through package deals. Explore free local attractions and utilise public transport options to minimise travel expenses while enjoying the scenic beauty of Chester.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are April to May and November, where the prices are slightly lower. This is in comparison to January to February and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Friday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Chester with your flights and activities through an Expedia package deal.

Find the best attractions near Chester

Chester, Vermont, is an ideal destination for skiing and adventure sports enthusiasts. Visitors can explore a variety of points of interest, including parks, state parks, and history museums, offering a rich blend of outdoor activities and cultural experiences. Whether you're seeking family-friendly adventures or a taste of local history, Chester provides a delightful array of attractions to suit every traveller's needs.

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

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.7°F (-6.3°C)Light RainMostly CloudySlightly LowSlightly High
February22.6°F (-5.2°C)Light RainMostly CloudySlightly LowSlightly High
March30.7°F (-0.7°C)Light RainMostly CloudySlightly LowAverage
April42.8°F (6.0°C)Light RainMostly CloudyAverageSlightly Low
May55.8°F (13.2°C)Light RainMostly SunnyAverageSlightly Low
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnySlightly HighAverage
August67.3°F (19.6°C)Light RainMostly SunnySlightly HighAverage
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
October48.6°F (9.2°C)Light RainMostly SunnyAverageSlightly High
November36.1°F (2.3°C)Light RainMostly SunnyAverageSlightly Low
December27.3°F (-2.6°C)Light RainMostly CloudyAverageAverage

The nearest major airports for your trip to Chester

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

Frequently asked questions

Where is the best place to stay in Chester?
Based on our traveler data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. 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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