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Chester hotels from RM378

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Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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Our top choices for Chester hotels

1. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
John
RM954
RM1,040 total
includes taxes & fees
13 Nov - 14 Nov
Stone Hearth Inn and Eatery

2. Fullerton Inn

Fullerton Inn
Chester Depot
United States
kris
RM527
RM574 total
includes taxes & fees
10 Nov - 11 Nov
Fullerton Inn

3. The Inn at Manchester

The Inn at Manchester
Manchester Village Historic District
United States
Reagan
RM570
RM721 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Manchester

4. Seesaw's Lodge

Seesaw's Lodge
Peru
United States
Michaela
RM905
RM986 total
includes taxes & fees
18 Oct - 19 Oct
Seesaw's Lodge

5. The Weston

The Weston
Weston
RM1,613
RM1,758 total
includes taxes & fees
20 Oct - 21 Oct
The Weston

6. Four Columns Inn

Four Columns Inn
Newfane
United States
cindy
RM437
RM476 total
includes taxes & fees
2 Nov - 3 Nov
Four Columns Inn

7. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Dorrie
RM926
RM1,160 total
includes taxes & fees
5 Nov - 6 Nov
The Inn at Weathersfield

8. The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
Manchester Village Historic District
United Kingdom
Tracey
RM935
RM1,029 total
includes taxes & fees
25 Oct - 26 Oct
The Reluctant Panther Inn and Restaurant

9. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
United States
gail
Harvest Barn Inn

10. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
Windsor
United States
Jessica
RM513
RM782 total
includes taxes & fees
1 Nov - 2 Nov
Fat Sheep Farm & Cabins

11. Colonel Williams Inn

Colonel Williams Inn
Brattleboro
United States
Amy
RM643
RM708 total
includes taxes & fees
20 Oct - 21 Oct
Colonel Williams Inn

12. Inn on Putney Road

Inn on Putney Road
Brattleboro
United States
Karla
RM1,090
RM1,199 total
includes taxes & fees
1 Nov - 2 Nov
Inn on Putney Road

13. The Inn at Ormsby Hill

The Inn at Ormsby Hill
Manchester Center
United States
Victoria
RM1,058
RM1,164 total
includes taxes & fees
10 Nov - 11 Nov
The Inn at Ormsby Hill

14. Stay At Jimmy's

Stay At Jimmy's
Woodstock
United States
Jeanne
RM1,221
RM1,343 total
includes taxes & fees
29 Oct - 30 Oct
Stay At Jimmy's

15. Farm Road Estate

Farm Road Estate
West Dover
RM790
RM1,093 total
includes taxes & fees
1 Nov - 2 Nov
Farm Road Estate

16. Inn At Mount Snow

Inn At Mount Snow
West Dover
United States
Barry
RM613
RM674 total
includes taxes & fees
1 Nov - 2 Nov
Inn At Mount Snow

17. The Jackson

The Jackson
West Woodstock
United States
Ava
RM503
RM553 total
includes taxes & fees
3 Nov - 4 Nov
The Jackson

18. 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

19. Deer Brook Inn

Deer Brook Inn
Woodstock
RM950
RM1,045 total
includes taxes & fees
3 Nov - 4 Nov
Deer Brook Inn

20. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Richard
RM689
RM748 total
includes taxes & fees
20 Oct - 21 Oct
The Carriage Barn Inn
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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

Fullerton Inn

Fullerton Inn

10/10 Excellent
"Stayed there 7yrs.ago and had another great experience this time, Cloe our waitress was excellent and made our dining alot of fun."
Tim 1-night trip
Posted 1 hour ago
Fullerton Inn
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

8/10 Good
"This is a great place but the description is a bit deceptive. Itโ€™s right off the highway and not on the Castle grounds. In fact we never saw the castle. I booked it thinking weโ€™d have a place to walk around and enjoy the grounds. Nope! The hotel was nice and the people were very friendly and helpful. We stayed in a suite and loved it. The fireplace and washer and dryer were exactly what we wanted and needed. I would stay here again but would just know youโ€™re not on the castle grounds."
Stephanie and Don 3-night trip
Posted 1 hour ago
Pointe at Castle Hill Resort
Aspen At Manchester

Aspen At Manchester

8/10 Good
"The location was perfect for shopping and dining in Manchester. Our room was clean and modern and had a nice television with streaming. Our refrigerator made a clanking noise throughout the night and one of the ice machines was not working. Grab and go breakfasts were supposed to be included, but found out that this was actually discontinued a few months ago. Overall, for the price it was acceptable but these small problems hopefully will be corrected."
kathleen 2-night trip
Posted 3 hours ago
Aspen At Manchester
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"Good"
Kenton 2-night trip
Posted 4 hours ago
The Equinox Golf Resort And Spa
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"I canโ€™t say enough about how enjoyable it was! Will be back!"
Allison 3-night trip
Posted 14 hours ago
Jackson Gore Village, A Vail Resorts Property
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Perfect for our one night stay. Rooms were clean. Staff were friendly and helpful. Restaurants within walkable distance."
Sarah 1-night trip
Posted 19 hours ago
Hampton Inn and Suites Manchester
The Manchester View

The Manchester View

8/10 Good
"Beautiful room, very clean and new. It was very bare in the room though. Breakfast from 8-10 and we went at 9:40, it was wiped out with nobody refilling so make sure you go early. Next day we went early and it was delicious! Hot tub was amazing which we used both nights. Overall, the views are gorgeous and highly recommend this hotel."
Marybeth 2-night trip
Posted 22 hours ago
The Manchester View
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

8/10 Good
"Hard to find the hot tub. Strange to not have staff there."
Ginger 1-night trip
Posted 2 days ago
Hideaway Inn Mt. Snow
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."
Teresa D 1-night trip
Posted 2 days ago
Best Western Plus Keene Hotel

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! (1,009 reviews)
The Putney Inn
The Manchester View

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT
RM414
RM455 total
3 Nov - 4 Nov
includes taxes & fees
9.4/10 Exceptional! (927 reviews)
The Manchester View
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
8.6/10 Excellent! (1,006 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
RM505
RM601 total
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (703 reviews)
Aspen At Manchester
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
RM579
RM637 total
1 Nov - 2 Nov
includes taxes & fees
Latchis Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT
RM621
RM684 total
1 Nov - 2 Nov
includes taxes & fees
9.6/10 Exceptional! (1,009 reviews)
Hampton Inn and Suites Manchester

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 lodgeโ€™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 Expediaโ€™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 Expediaโ€™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
January20.7ยฐF (-6.3ยฐC)Light RainMostly CloudySlightly LowSlightly High
February22.6ยฐF (-5.2ยฐC)Light RainMostly CloudySlightly LowSlightly High
March30.7ยฐF (-0.7ยฐC)Light RainMostly CloudySlightly LowAverage
April42.8ยฐF (6.0ยฐC)Light RainMostly CloudyAverageSlightly Low
May55.8ยฐF (13.2ยฐC)Light RainMostly SunnyAverageSlightly Low
June63.1ยฐF (17.3ยฐC)Light RainMostly SunnyAverageAverage
July69.3ยฐF (20.7ยฐC)Light RainMostly SunnySlightly HighAverage
August67.3ยฐF (19.6ยฐC)Light RainMostly SunnySlightly HighAverage
September60.3ยฐF (15.7ยฐC)Light RainMostly SunnySlightly HighAverage
October48.6ยฐF (9.2ยฐC)Light RainMostly SunnyAverageSlightly High
November36.1ยฐF (2.3ยฐC)Light RainMostly SunnyAverageSlightly Low
December27.3ยฐF (-2.6ยฐC)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 18ยฐC, while the coldest months are January and February, with an average of -4ยฐC. 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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