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26 Sep - 27 Sep
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27 Sep - 28 Sep
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2 Oct - 4 Oct
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9 Oct - 11 Oct

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Lisa
AED 584
AED 637 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
AED 953
AED 1,039 total
includes taxes & fees
28 Sep - 29 Sep
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
AED 658
AED 724 total
includes taxes & fees
18 Oct - 19 Oct
Best Western Springfield Hotel

4. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
AED 855
AED 1,067 total
includes taxes & fees
28 Sep - 29 Sep
The Inn at Weathersfield

5. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
AED 621
AED 708 total
includes taxes & fees
18 Oct - 19 Oct
Pointe at Castle Hill Resort

6. The Hartness House

The Hartness House
Springfield
United States
Gregory
AED 759
AED 835 total
includes taxes & fees
25 Oct - 26 Oct
The Hartness House

7. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
AED 304
AED 348 total
includes taxes & fees
28 Sep - 29 Sep
The Upper Pass Lodge at Magic Mountain

8. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
AED 820
AED 894 total
includes taxes & fees
20 Oct - 21 Oct
Castle Hill Resort And Spa

9. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
United States
Raedene
AED 754
AED 822 total
includes taxes & fees
27 Sep - 28 Sep
COHO Inn & Motor Lodge

10. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
United States
Victoria
AED 674
AED 732 total
includes taxes & fees
18 Oct - 19 Oct
The Common Man Inn & Restaurant

11. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
AED 657
AED 723 total
includes taxes & fees
25 Oct - 26 Oct
Blue Gentian Lodge at Magic Mountain

12. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
David
AED 607
AED 737 total
includes taxes & fees
30 Sep - 1 Oct
Jackson Gore Village, A Vail Resorts Property

13. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
EDWARD S
AED 392
AED 426 total
includes taxes & fees
27 Oct - 28 Oct
Claremont Motor Lodge

14. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
Kristina
AED 932
AED 1,025 total
includes taxes & fees
28 Sep - 29 Sep
Main and Mountain Bar & Motel

15. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
Bromley Mountain
United States
Mary
AED 531
AED 585 total
includes taxes & fees
29 Sep - 30 Sep
Sun Lodge near Manchester VT, Ascend Collection Hotel

16. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
United States
DENNIS
AED 495
AED 599 total
includes taxes & fees
28 Sep - 29 Sep
The Black Bear Lodge at Stratton Mountain Resort

17. The Putney Inn

The Putney Inn
Putney
United States
JANE
AED 309
AED 340 total
includes taxes & fees
25 Oct - 26 Oct
The Putney Inn

18. Otherland Hotel

Otherland Hotel
Newfane
Canada
Omar
AED 365
AED 514 total
includes taxes & fees
28 Sep - 29 Sep
Otherland Hotel

19. Royal Inn Claremont

Royal Inn Claremont
Claremont
United States
Eva
AED 441
AED 478 total
includes taxes & fees
28 Sep - 29 Sep
Royal Inn Claremont

20. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Shannon
AED 584
AED 697 total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most.

Chester Depot

If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

Stay near popular Chester attractions

Bonnie's Bundles Dolls

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

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

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

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

Top Chester Hotel Reviews

Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"We're not usually 'motel' people so we were skeptical. Turns out it was such a great place...clean, comfortable. We would definitely recommend."
Cheryl 1-night trip
Posted 4 hours ago
Aspen At Manchester
The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"We loved everything about this hotel. It was a short walk to get downtown. Rooms were very clean. We loved the different areas for coffee so we didn’t have to walk too far in the morning."
Renee 2-night trip
Posted 7 hours ago
The Shire Woodstock
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Very nice staff, clean room and good breakfast."
Deborah 1-night trip
Posted 19 hours ago
Hampton Inn and Suites Manchester
The Manchester View

The Manchester View

10/10 Excellent
"Property has been renovated-it is very clean and modern. Nice simple breakfast served. Housekeeping didn’t show the 2nd day of our stay. ( we hunted them down for towels before getting ready for a wedding. They offered to come then- but it was too late in the day) Great views and quite location."
Cynthia 2-night trip
Posted 21 hours ago
The Manchester View
Fullerton Inn

Fullerton Inn

8/10 Good
"Staff was very friendly. It was quiet. Location was perfect if you want to be located in a small quaint picturesque town. Charming."
Lisa 2-night trip
Posted 1 day ago
Fullerton Inn
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Nice hot tubs"
David 3-night trip
Posted 2 days ago
Jackson Gore Village, A Vail Resorts Property
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."
Nancy 3-night trip
Posted 3 days ago
The Equinox Golf Resort And Spa
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice stay and nice rooms."
Nicole 1-night trip
Posted 4 days ago
Pointe at Castle Hill Resort
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 4 days ago
Stone Hearth Inn and Eatery

More cheap stays in Chester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
AED 309
AED 340 total
25 Oct - 26 Oct
includes taxes & fees
The Putney Inn
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
AED 394
AED 434 total
26 Oct - 27 Oct
includes taxes & fees
9.4/10 Exceptional! (907 reviews)
The Manchester View
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
AED 435
AED 479 total
28 Sep - 29 Sep
includes taxes & fees
8.6/10 Excellent! (989 reviews)
Latchis Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
AED 455
AED 494 total
27 Oct - 28 Oct
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
AED 438
AED 522 total
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (693 reviews)
Aspen At Manchester
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
AED 569
AED 626 total
26 Oct - 27 Oct
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
Hampton Inn and Suites Manchester

Hotels in Chester with star-rating

Find out more about Chester

Top reasons to visit Chester

  • Outstanding Skiing Opportunities: Chester is a haven for ski enthusiasts with various local ski resorts offering thrilling winter sports.
  • Charming Local Shops: The town features quirky boutiques that provide a unique shopping experience, adding to Chester's charm.
  • Beautiful Parks and Nature: Visitors can explore stunning parks and state parks, perfect for outdoor adventures and family outings.
  • Rich Historical Sites: Chester boasts historical museums and sites, enriching your understanding of the local culture.
  • Diverse Lodging Options: From cozy B&Bs to unique agritourism stays, Chester offers accommodations for every type of traveler.

Find great hotels near Chester

Experience the charm of Chester, Vermont, with a variety of lodging options that cater to every traveler. From cozy bed & breakfasts to unique agritourism properties, you'll find accommodations perfect for family adventures or pet-friendly getaways. Explore Chester's hotels and inns, read reviews, and discover the perfect hotel rooms to make your stay memorable in this picturesque destination.

  • Best Western Springfield Hotel: Nestled 12.9km from Chester, Best Western Springfield Hotel is a welcoming retreat for pet owners and their furry friends. This hotel prides itself on providing a pet-friendly atmosphere, ensuring that your pets are treated with care. With amenities such as designated dog areas and a flexible pet policy, it caters to travelers looking for a comfortable stopover. The hotel features cozy accommodations, complimentary breakfast, and a fitness center, making it an ideal choice for families and those seeking a convenient base to explore the surrounding area.
  • Pointe at Castle Hill Resort: Located 14.5km from Chester, Pointe at Castle Hill Resort offers a luxurious escape for adventure enthusiasts and business travelers alike. This 3.5-star hotel features an array of exciting activities such as rafting, hiking, and skiing nearby, ensuring an action-packed stay. Guests can unwind at the full-service spa, which includes rejuvenating body wraps and facial treatments, or take a dip in the pool and hot tub. The resort's elegant accommodations and business facilities make it a perfect blend of relaxation and productivity, appealing to those who seek both adventure and comfort.
  • Jackson Gore Village: Situated 20.9km from Chester, Jackson Gore Village is an excellent choice for those who love skiing and golfing. This 3-star hotel offers direct access to ski lifts and shuttles, making it easy for guests to hit the slopes. With on-site amenities for snow tubing and snowshoeing, adventure is right at your doorstep. Golf enthusiasts will appreciate the nearby golfing opportunities, while comfortable accommodations provide a cozy retreat after a day of outdoor activities. Jackson Gore Village is perfect for families and groups looking for a fun-filled getaway.

Where to stay near Chester

Chester, Vermont, is a charming destination perfect for a weekend getaway, offering a mix of relaxation and adventure. Explore downtown Chester for its friendly atmosphere and historical sites, or head to nearby areas for skiing and outdoor sports. With various recreational opportunities, you can enjoy both budget-friendly and luxurious experiences. Whether you're seeking thrilling activities or a peaceful retreat, Chester has something for every traveler to enjoy.

  • Ludlow: Nestled 17.7km from Chester, Ludlow is a charming city known for its vibrant ski culture. Visitors flock here for thrilling winter sports and adventure activities, making it a popular destination from December to February. The ski fields and resorts are prime spots for both novices and seasoned skiers. In addition to winter sports, Ludlow's stunning natural landscapes, including lakes and mountains, provide the perfect backdrop for outdoor enthusiasts year-round.
  • Springfield: Located just 9.7km from Chester, Springfield offers a diverse travel experience with a mix of adventure and nature. The city attracts visitors throughout the year, with peak seasons occurring in February, July, and September. Known for its ski resorts and outdoor activities, Springfield is a hub for sports lovers. Nearby attractions, including lakes and national state parks, invite exploration and relaxation, making it a well-rounded destination for all types of travelers.
  • Grafton: Situated 9.7km away from Chester, Grafton is a picturesque city that draws visitors for its outdoor adventures and stunning scenery. With peak travel times in July and September to October, Grafton is perfect for those seeking both adrenaline-pumping activities and serene landscapes. The nearby ski fields and resorts cater to winter sports enthusiasts, while the surrounding valleys and mountains offer breathtaking views and trails for hiking and exploring in the warmer months.

Things to do near Chester

Chester, Vermont, is a perfect destination for ski enthusiasts and adventure seekers. Visitors can enjoy a variety of skiing options at local ski resorts, along with numerous outdoor activities. Beyond the slopes, the town features quirky shops that add a unique charm to your experience. Whether you're hitting the trails or exploring the local boutiques, Chester offers a delightful mix of adventure and leisure for every traveler.

Shopping

In Chester, you can shop at the Vermont Country Store and My Minds Design, both located 9.7km away. If you're up for a drive, visit the West River Farmers Market, 17.7km away, for a vibrant local market experience with fresh produce and unique crafts.

Recreation

Fox Run Golf Course offers a picturesque setting for golf enthusiasts, featuring lush greens and outdoor activities just 19.3km from Chester. For a more relaxed atmosphere, visit The Ice House Ice Skating, located 20.9km away, where you can enjoy skating in a tranquil environment. Stratton Mountain Golf Course, also 20.9km away, provides more outdoor sports opportunities amidst stunning views.

Adventure

At Okemo Mountain Resort, 17.7km from Chester, experience thrilling skiing and snowboarding on diverse trails. The Solitude Express Ski Lift, located 19.3km away, offers breathtaking views and easy access to adventure slopes. For an unforgettable experience, soar through the skies at Morningside Flight Park, also 19.3km from Chester.

Nightlife

Experience a vibrant nightlife in Chester with a visit to the Weston Playhouse for captivating performances, or enjoy family fun at Maple Lanes arcade. For a dose of culture, catch a show at the Bellows Falls Opera House, where romance and entertainment blend seamlessly.

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

Booking tips and Expedia advantages for Chester

To save money on your trip to Chester, Vermont, consider visiting during the off-peak months of April to May or November, when accommodation prices are lower. Tuesdays are the cheapest days to stay, while Fridays tend to be more expensive. Use Expedia to filter for budget-friendly hotels and combine your bookings for flights and activities to secure package deals. Additionally, explore free local attractions and utilize public transport for affordable travel around the area, ensuring a memorable yet cost-effective vacation.

  • 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: Utilize Expedia's search tool to customize your preferences, such as budget, desired location, and the type of hotel you’re looking for. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservations 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 ski enthusiasts and adventure seekers, offering a variety of outdoor activities and cultural experiences. Visitors can explore beautiful parks, historical museums, and state parks that cater to families and travelers looking for enriching experiences. Whether you're in the mood for sports or simply soaking in the local history, Chester provides a unique blend of nature and culture for an unforgettable vacation.

  • Vermont Museum of Mining and Minerals: Located 9.7km from Chester, this museum offers a fascinating glimpse into Vermont's mining history. Families can explore interactive exhibits and discover the rich geological resources of the region, making it both educational and entertaining.
  • Lowell Lake State Park: Just 14.5km away, this state park is a haven for outdoor enthusiasts. With its stunning scenery, visitors can enjoy hiking, fishing, and picnicking amidst nature’s beauty, providing a perfect backdrop for adventure seekers.
  • Grafton Historical Society: Situated 9.7km from Chester, this historical society presents a deep dive into local history. Visitors can appreciate the cultural heritage of the area through exhibits and artifacts, enriching their understanding of Grafton's past.

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

When visiting Chester, Vermont, there are several nearby airports to consider. Lebanon Municipal Airport (LEB) is located 46.7km away, with nearby accommodations like the 4-star Hanover Inn Dartmouth, 8.0km from the airport, and the 3-star Hotel Coolidge, 3.2km away. Rutland Southern Vermont Regional Airport (RUT) is 28.0km away, featuring hotels such as the 3.5-star Killington Mountain Lodge, 17.7km from the airport, and the Snowed Inn, also 17.7km away. The closest option is Hartness State Airport (VSF) in Springfield, just 11.3km away, with the 4-star Inn at Weathersfield located 1.6km from the airport, offering convenient access to Chester.

Frequently asked questions

What's the top vacation rental that Chester has to offer?
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: Visitors like this Chester vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. 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 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.
Where can I learn more about changing or cancelling my trip to Chester?
For additional details about rescheduling or cancelling your trip to Chester, head over to our customer service page.
What's the best hotel for a family vacation to Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a guesthouse with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families. Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are also fun for kids of all ages. Find more child-friendly accommodations in Chester.
What's the best accommodation for a romantic vacation in Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favorite guesthouse for couples, and features free WiFi and a garden. See all romantic hotels in Chester.
What's the best pet-friendly accommodation in Chester?
Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains is a top pet-friendly option for your stay. Motel in the Meadow is another good choice for you and your pet. 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. The Manchester View and Pointe at Castle Hill Resort are two additional hotels with an onsite pool. View all hotels with pools in Chester.
What's the best accommodation near Hartness State Airport (VSF)?
The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.
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 66 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. 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.