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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 AEDĀ 474
AEDĀ 516 total
includes taxes & fees
24 Nov - 25 Nov
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 AEDĀ 683
AEDĀ 744 total
includes taxes & fees
19 Nov - 20 Nov
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 AEDĀ 559
AEDĀ 615 total
includes taxes & fees
17 Nov - 18 Nov
Best Western Springfield Hotel

4. 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 AEDĀ 585
AEDĀ 638 total
includes taxes & fees
28 Nov - 29 Nov
Harvest Barn Inn

5. 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 AEDĀ 745
AEDĀ 947 total
includes taxes & fees
30 Nov - 1 Dec
The Inn at Weathersfield

6. 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 AEDĀ 499
AEDĀ 569 total
includes taxes & fees
17 Nov - 18 Nov
Pointe at Castle Hill Resort

7. 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 AEDĀ 705
AEDĀ 775 total
includes taxes & fees
17 Nov - 18 Nov
The Hartness House

8. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (450 reviews)
"We enjoyed our stay here."
United States
Anna
The price is AEDĀ 476
AEDĀ 517 total
includes taxes & fees
15 Nov - 16 Nov
The Common Man Inn & Restaurant

9. 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 AEDĀ 309
AEDĀ 353 total
includes taxes & fees
16 Nov - 17 Nov
The Upper Pass Lodge at Magic Mountain

10. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (612 reviews)
"Room was clean and parking was right out front."
United States
Cindy
The price is AEDĀ 419
AEDĀ 454 total
includes taxes & fees
15 Nov - 16 Nov
Claremont Motor Lodge

11. 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 AEDĀ 587
AEDĀ 640 total
includes taxes & fees
22 Nov - 23 Nov
The Landgrove

12. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
2.0 star property
Weston
9.4 out of 10, Exceptional, (80 reviews)
"Quiet and peaceful."
United States
James
The price is AEDĀ 655
AEDĀ 713 total
includes taxes & fees
30 Nov - 1 Dec
COHO Inn & Motor Lodge

13. 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 AEDĀ 618
AEDĀ 674 total
includes taxes & fees
15 Nov - 16 Nov
Castle Hill Resort And Spa

14. The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (969 reviews)
"Great breakfast as well as a lovely property!"
United States
Pauline
The price is AEDĀ 417
AEDĀ 458 total
includes taxes & fees
15 Nov - 16 Nov
The Manchester View

15. 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)
"Great place, great location, super friendly staff and excellent amenities."
United States
Gerald
The price is AEDĀ 471
AEDĀ 519 total
includes taxes & fees
29 Nov - 30 Nov
Hampton Inn and Suites Manchester

16. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,001 reviews)
"Great location and wonderful staff! I love staying here every year!"
United States
Kristen
The price is AEDĀ 294
AEDĀ 323 total
includes taxes & fees
13 Dec - 14 Dec
The Putney Inn

17. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
3.5 star property
Bromley Mountain
8.8 out of 10, Excellent, (356 reviews)
"The people at the front desk were extremely friendly and helpful."
United States
Marcia
The price is AEDĀ 379
AEDĀ 417 total
includes taxes & fees
2 Dec - 3 Dec
Sun Lodge near Manchester VT, Ascend Collection Hotel

18. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (504 reviews)
"Great amenities, fantastic views, very clean, excellent breakfast!"
United States
BARBARA
The price is AEDĀ 273
AEDĀ 300 total
includes taxes & fees
22 Nov - 23 Nov
Bromley View Inn

19. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (129 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is AEDĀ 547
AEDĀ 602 total
includes taxes & fees
15 Nov - 16 Nov
Blue Gentian Lodge at Magic Mountain

20. 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 AEDĀ 678
AEDĀ 824 total
includes taxes & fees
18 Nov - 19 Nov
Jackson Gore Village, A Vail Resorts Property
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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

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

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.
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. Aspen At Manchester and The Manchester View 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 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.