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Chester hotels from RM283

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5 Oct - 6 Oct
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6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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Our top choices for Chester hotels

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
kris
RM609
RM663 total
includes taxes & fees
1 Nov - 2 Nov
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
John
RM1,152
RM1,256 total
includes taxes & fees
6 Oct - 7 Oct
Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
RM621
RM683 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Springfield Hotel

4. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
RM603
RM687 total
includes taxes & fees
21 Oct - 22 Oct
Pointe at Castle Hill Resort

5. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
RM926
RM1,160 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Weathersfield

6. The Hartness House

The Hartness House
Springfield
United States
Elizabeth
RM809
RM890 total
includes taxes & fees
1 Nov - 2 Nov
The Hartness House

7. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
gail
RM621
RM677 total
includes taxes & fees
3 Nov - 4 Nov
Harvest Barn Inn

8. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
RM443
RM507 total
includes taxes & fees
1 Nov - 2 Nov
The Upper Pass Lodge at Magic Mountain

9. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
Claremont
Canada
Bruce
RM529
RM574 total
includes taxes & fees
1 Nov - 2 Nov
The Common Man Inn & Restaurant

10. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Daniel
RM736
RM894 total
includes taxes & fees
26 Oct - 27 Oct
Jackson Gore Village, A Vail Resorts Property

11. Claremont Motor Lodge

Claremont Motor Lodge
Claremont
United States
Jerri
RM490
RM532 total
includes taxes & fees
18 Oct - 19 Oct
Claremont Motor Lodge

12. The Manchester View

The Manchester View
Manchester Center
United States
Gregory
RM345
RM379 total
includes taxes & fees
3 Nov - 4 Nov
The Manchester View

13. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
United States
Rosemary
RM600
RM659 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn and Suites Manchester

14. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
RM1,099
RM1,198 total
includes taxes & fees
19 Oct - 20 Oct
Castle Hill Resort And Spa

15. Bromley View Inn

Bromley View Inn
Bondville
Canada
William
RM330
RM363 total
includes taxes & fees
1 Nov - 2 Nov
Bromley View Inn

16. The Putney Inn

The Putney Inn
Putney
United States
Elizabeth G
RM344
RM378 total
includes taxes & fees
25 Oct - 26 Oct
The Putney Inn

17. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
Ludlow
United States
Patricia
RM825
RM907 total
includes taxes & fees
12 Oct - 13 Oct
Main and Mountain Bar & Motel

18. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Shannon
RM649
RM775 total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

19. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
RM456
RM502 total
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn & Suites Brattleboro I-91

20. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
United States
Raedene
RM948
RM1,034 total
includes taxes & fees
12 Oct - 13 Oct
COHO Inn & Motor Lodge
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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, 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

Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"Great place, but a bit over priced for what it is"
Steven 3-night trip
Posted 4 hours ago
Aspen At Manchester
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good
"Clean room and good breakfast. Affordable and conveniently located for our visit. Carpets are worn out and dirty."
Karina 2-night trip
Posted 5 hours ago
The Black Bear Lodge at Stratton Mountain Resort
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"By far, our favorite place to stay at as a family. The staff is always very friendly, courteous and kind, and the property is breathtaking. The views of the mountains and the foliage were absolutely stunning. The rooms are spacious and well taken care of. We especially enjoyed the hot tubs with the Mountain View."
Emily 1-night trip
Posted 8 hours ago
Jackson Gore Village, A Vail Resorts Property
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

10/10 Excellent
"Really good place"
paul 2-night trip
Posted 16 hours ago
Hideaway Inn Mt. Snow
Colonial Motel

Colonial Motel

10/10 Excellent
"clean room"
Biplob 1-night trip
Posted 1 day ago
Colonial Motel
The Jackson

The Jackson

10/10 Excellent
"Staff extremely helpful at check in. Welcome wine n cheese for quests was a wonderful start too our evening. Beds were comfortable and bathrooms nice but a little small."
Howard 1-night trip
Posted 1 day ago
The Jackson
Fullerton Inn

Fullerton Inn

10/10 Excellent
"Great place. Made our anniversary amazing. Thank you"
kris 1-night trip
Posted 1 day ago
Fullerton Inn
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice place, quiet and easily accessible. Room was large with separate large bedroom with door. Large LR with fireplace, sofa & recliner and fully stocked kitchen."
Mary 2-night trip
Posted 3 days ago
Pointe at Castle Hill Resort
On The River Inn

On The River Inn

8/10 Good
"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."
Loxley 3-night trip
Posted 4 days ago
On The River Inn

More cheap stays in Chester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
RM344
RM378 total
25 Oct - 26 Oct
includes taxes & fees
8.4/10 Very good! (1,004 reviews)
The Putney Inn
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
RM345
RM379 total
3 Nov - 4 Nov
includes taxes & fees
The Manchester View
Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
RM421
RM508 total
2 Nov - 3 Nov
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
RM486
RM527 total
2 Nov - 3 Nov
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
RM600
RM659 total
1 Nov - 2 Nov
includes taxes & fees
Hampton Inn and Suites Manchester
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
RM728
RM801 total
7 Oct - 8 Oct
includes taxes & fees
Latchis Hotel

Find out more about Chester

Top reasons to visit Chester

  • Adventure Sports: Chester is a fantastic destination for skiing and outdoor sports enthusiasts, with local resorts and ski fields offering thrilling experiences.
  • Parks and Nature: Explore picturesque parks and nearby state parks, perfect for enjoying the stunning autumn scenery and outdoor activities.
  • Cultural Attractions: Discover local history through museums, art galleries, and agricultural exhibits that showcase the region's vibrant culture.
  • Charming Accommodations: Enjoy a variety of cosy bed & breakfasts and agritourism properties, many of which are pet-friendly.
  • Friendly Atmosphere: Experience the warm and inviting community spirit that Chester offers, making it a delightful place to visit.

Find great hotels near Chester

Chester, Vermont, offers a delightful selection of accommodations, including charming agritourism properties and cosy bed & breakfasts. Ideal for families and adventure seekers, many hotels provide pet-friendly options, air conditioning, and American breakfast. With a variety of affordable choices and spacious suites, you're sure to find the perfect base for your holiday exploration in this picturesque locale.

  • Jackson Gore Village: Nestled 20.9km from Chester, Jackson Gore Village is a charming 3-star hotel that offers a delightful family-friendly and spa-themed retreat. Perfect for travellers seeking a relaxing vacation, the property boasts a range of amenities tailored for children, including a shared playground, onsite mini-golf, and an arcade game room. Guests can indulge in rejuvenating spa services such as massages and reflexology, while the indoor pool provides a serene environment for relaxation. Golf enthusiasts will appreciate the nearby golf experiences, making this a fantastic choice for both family fun and leisure.
  • The Upper Pass Lodge at Magic Mountain: Located 16.1km from Chester, The Upper Pass Lodge at Magic Mountain embodies the spirit of adventure. This pet-friendly motel is ideal for thrill-seekers, offering an array of exciting activities such as skiing, snowshoeing, and nearby horse riding. The lodge warmly welcomes pets, ensuring your furry companions can join in the fun without any extra charge. With its focus on outdoor recreation, guests can easily access adventure sports and enjoy the breathtaking natural beauty of the area, making it a top pick for an exciting getaway.
  • Claremont Motor Lodge: Situated 24.1km from Chester, Claremont Motor Lodge is a welcoming motel that prioritises comfort and entertainment. Guests can unwind with a selection of in-room entertainment options, including cable TV and LCD screens, ensuring a relaxing evening after a day of exploration. The lodge’s convenient location provides easy access to local attractions while maintaining a peaceful atmosphere. With its focus on providing a comfortable stay, Claremont Motor Lodge is a reliable choice for those seeking a straightforward yet enjoyable lodging experience.

Where to stay near Chester

Chester, Vermont, offers a charming blend of adventure and relaxation, perfect for those seeking a memorable vacation. With its picturesque autumn scenery and friendly atmosphere, visitors can indulge in skiing and outdoor sports, or simply unwind in its beautiful surroundings. Nearby towns boast historical charm and luxurious experiences, making Chester an ideal base for exploring nature and celebrating the region's vibrant culture.

  • Ludlow: Nestled 17.7km from Chester, Ludlow is a vibrant city that draws visitors year-round, particularly during the ski season from December to February. This region is a haven for adventure enthusiasts, offering a plethora of outdoor sports and activities. The local ski resorts and fields provide exhilarating experiences for both novice and seasoned skiers. Beyond the slopes, Ludlow boasts stunning natural landscapes, including picturesque lakes, majestic mountains, and serene valleys, making it an ideal spot for breathtaking vistas and relaxation.
  • Springfield: Just 9.7km away from Chester, Springfield is a charming city that welcomes visitors throughout the year, with notable peaks in February, July, and September. This locale is perfect for those seeking adventure, particularly in skiing and outdoor sports. Springfield's proximity to various ski resorts and fields adds to its appeal. Additionally, the nearby natural state park offers opportunities for hiking and exploration, while the area's lakes and mountains provide a stunning backdrop for outdoor activities, ensuring a memorable visit.
  • Grafton: Located a mere 9.7km from Chester, Grafton is a quaint city that attracts tourists, especially in the warmer months of July and September to October. Known for its outdoor adventures, Grafton offers excellent skiing opportunities alongside its scenic ski fields and resorts. Visitors can explore the beautiful lakes, valleys, and mountains that surround the area, providing a perfect blend of relaxation and adventure. Grafton's charming atmosphere and natural beauty make it a delightful destination for those looking to immerse themselves in the great outdoors.

Things to do near Chester

Chester, Vermont, is perfect for a skiing and adventure holiday, offering a variety of activities such as skiing at local resorts and exploring ski fields. Visitors can also enjoy day trips, animal shows, agricultural exhibits, and art galleries, providing a well-rounded experience of the area's culture and natural beauty. Embrace the charm of Chester while indulging in both outdoor sports and local attractions.

Shopping

In Chester, you can visit Vermont Country Store and My Minds Design, both offering unique gifts and souvenirs just 9.7km away. If you're up for a drive, check out the West River Farmers Market, located 17.7km away, where you can find local produce and crafts in a vibrant atmosphere.

Recreation

The Ice House Ice Skating, located 20.9km from Chester, offers a delightful recreational experience with a focus on wellness and relaxation. For sports enthusiasts, Crown Point Golf Course, 12.9km away, provides an invigorating outdoor golfing experience, while Fox Run Golf Course, 19.3km from Chester, promises thrilling outdoor sports vibes.

Adventure

Morningside Flight Park offers a breathtaking scenic flight experience, located 19.3km from Chester, where you can enjoy stunning views and an exhilarating adventure. For winter sports enthusiasts, Okemo Mountain Resort, situated 17.7km away, provides thrilling skiing opportunities, while the Solitude Express Ski Lift, also 19.3km distant, enhances your skiing experience.

Nightlife

In Chester, the Weston Playhouse offers a charming theatre experience, showcasing romance and culture just 16.1km away. For adventure lovers, Maple Lanes provides thrilling arcade fun 22.5km away, while the Timber Ripper Mountain Coaster promises excitement with its exhilarating rides just 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

To save money during your visit to Chester, plan your trip between April to May or November when accommodation prices are lower. Consider staying on a Tuesday for the best rates, as Fridays tend to be the most expensive. Use Expedia’s search tool to compare prices and find the best deals, and consider booking a package that includes flights and activities for additional savings. Take advantage of free activities in the area and utilise local public transport to keep travel 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 preferred hotel type. To discover the best prices and offers, sort 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.

Find the best attractions near Chester

Chester, Vermont, offers a delightful blend of adventure and culture, making it ideal for ski and sports enthusiasts. Visitors can explore the picturesque parks and nearby state parks, as well as delve into local history at the museums. With activities catering to outdoor lovers and families alike, Chester is a charming destination for those seeking both thrill and cultural experiences.

  • Vermont Museum of Mining and Minerals: Discover the fascinating world of geology and mining at this engaging museum, located a mere 9.7km from Chester. With hands-on exhibits and a rich collection, it's an educational experience for the whole family, immersing you in the cultural heritage of Vermont.
  • Lowell Lake State Park: A splendid national park situated 14.5km away, Lowell Lake State Park offers breathtaking scenery and abundant opportunities for outdoor adventures. Enjoy hiking, fishing, or simply relaxing amidst nature's beauty in this tranquil setting.
  • Grafton Historical Society: Located just 9.7km from Chester, this history museum provides a glimpse into the region's past. With its charming exhibits and cultural vibes, it's an excellent spot to learn about local history and heritage.

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

Chester, Vermont, is conveniently accessible via several airports. Lebanon Municipal Airport (LEB) is situated 46.7km away, with nearby accommodation such as the Windsor Mansion Inn, a charming 3.5-star bed and breakfast 16.1km from the airport, and the 3-star Hotel Coolidge, located 3.2km away. Rutland Southern Vermont Regional Airport (RUT) is 40.2km from Chester, offering options like the Killington Mountain Lodge, a 3.5-star hotel 17.7km from the airport, and the 3-star Cortina Inn, just 6.4km away. For the closest option, Hartness State Airport (VSF) is a mere 11.3km from Chester, with the 4-star Inn at Weathersfield located 1.6km away.

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. Aspen At Manchester and The Manchester View 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 67 hotels and other accommodation options to choose from. Find out more about Chester.
What should I do while I'm visiting Chester?
A couple of favourite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. You'll also find Vermont Country Store and Lowell Lake State Park in the area. Take a look at what more there is to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.

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