Chester hotels from RM422

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chester hotels

Fullerton Inn

2.5 star property
Chester Depot
8.2 out of 10, Very good, (400)
"A unique inn in a charming town. Breakfast falls short, but staff is friendly and helpful "
United States
Dominique
The price is RM539
RM587 total
includes taxes & fees
9 Dec - 10 Dec
Fullerton Inn

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (105)
"Room was super quiet and clean. "
United States
Ernest
The price is RM872
RM951 total
includes taxes & fees
20 Nov - 21 Nov
Stone Hearth Inn and Eatery

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (546)
"I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn"
United States
Kevin
The price is RM1,374
RM1,695 total
includes taxes & fees
30 Nov - 1 Dec
Woodstock Inn & Resort

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (877)
"Everything was awesome! Great view and very clean. Just what we were looking for. Very easy check in and out"
United States
Ahmed
The Shire Woodstock

Aspen At Manchester

2.5 star property
Manchester Center
8.8 out of 10, Excellent, (598)
"Very nice hotel. Clean and looked recently remodeled. It was very quiet, allowing me to relax. Will stay here again when in the area."
United States
Grant
The price is RM447
RM538 total
includes taxes & fees
30 Nov - 1 Dec
Aspen At Manchester

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (540)
"Great motel with complete amenities.. beautiful surrounding especially in this fall"
United States
Giana
The price is RM432
RM659 total
includes taxes & fees
20 Nov - 21 Nov
Sleep Woodstock Motel

The Palmer House Resort, an Ascend Collection Hotel

3.0 star property
Manchester Center
8.4 out of 10, Very good, (853)
"The area around the Palmer House is so beautiful. Mountains everywhere!! "
United States
Mark
The price is RM422
RM533 total
includes taxes & fees
30 Nov - 1 Dec
The Palmer House Resort, an Ascend Collection Hotel

Hampton Inn and Suites Manchester

2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1001)
"The hotel was clean, the staff was friendly, and was a great location. The new Brewery on the property was great as well!"
United States
Jake
The price is RM531
RM584 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn and Suites Manchester

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
Stratton
7.6 out of 10, Good, (931)
"Great place for the price "
United States
Karen
The price is RM622
RM753 total
includes taxes & fees
10 Nov - 11 Nov
The Black Bear Lodge at Stratton Mountain Resort

The Covered Bridge Inn

2.5 star property
Brattleboro
7.6 out of 10, Good, (1002)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is RM384
RM422 total
includes taxes & fees
9 Nov - 10 Nov
The Covered Bridge Inn

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very good, (1001)
"Hotel was great."
United States
Heidi
The price is RM622
RM675 total
includes taxes & fees
10 Nov - 11 Nov
Best Western Plus Keene Hotel

Kimpton Taconic Hotel by IHG

4.0 star property
Manchester
9.4 out of 10, Exceptional, (812)
"Very nice, beautiful inn"
United States
Susan
The price is RM664
RM891 total
includes taxes & fees
1 Dec - 2 Dec
Kimpton Taconic Hotel by IHG

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (564)
"Nice old Inn!"
United States
Daniel
The price is RM459
RM728 total
includes taxes & fees
16 Nov - 17 Nov
The Equinox Golf Resort & Spa

Pointe at Castle Hill Resort

3.5 star property
Cavendish
8.8 out of 10, Excellent, (912)
"Nice clean room and friendly staff. I was there off season (early November) so some restaurants weren’t open but there were still plenty of options. "
United States
Andrew
The price is RM664
RM757 total
includes taxes & fees
11 Nov - 12 Nov
Pointe at Castle Hill Resort

Days Inn by Wyndham Keene NH

2.0 star property
Keene
7.0 out of 10, Good, (1000)
"Very professional people good service good staff "
United States
George
The price is RM423
RM459 total
includes taxes & fees
10 Nov - 11 Nov
Days Inn by Wyndham Keene NH

The Manchester View

2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (771)
"The setting is quiet peaceful and the accommodation is like home "
United States
diane
The Manchester View

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1007)
"Friendly, efficient staff and a very clean and nice room"
United States
Margaret
The price is RM594
RM653 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (622)
"Loved my stay"
United States
Christine
The price is RM635
RM689 total
includes taxes & fees
7 Dec - 8 Dec
Riverside Hotel, an Ascend Collection Hotel

Vantage Point Villas at Stratton Mountain Resort

3.0 star property
Stratton
8.4 out of 10, Very good, (70)
"Great place to stay! We went on a last minute Father’s Day weekend trip and had the best time! Great location close to the shops and restaurants. "
United States
Roberta
The price is RM1,040
RM1,292 total
includes taxes & fees
11 Nov - 12 Nov
Vantage Point Villas at Stratton Mountain Resort

Mount Snow Grand Summit Resort

3.0 star property
West Dover
8.8 out of 10, Excellent, (242)
"Free shuttle service to Dover is wonderful! Staff were friendly and helpful."
United States
Chris
The price is RM618
RM739 total
includes taxes & fees
16 Nov - 17 Nov
Mount Snow Grand Summit Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

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, DaVallia Art & Accents and Bonnie's Bundles Dolls 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.

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

More cheap stays in Chester

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?
Stone Hearth Inn and Eatery is ranked highly by Expedia customers. This B&B offers free breakfast and free parking. Another top choice for your trip based on reviews is Fullerton Inn. 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. Pointe at Castle Hill Resort and The Equinox Golf Resort & Spa 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 Grafton Historical Society and Vermont Country Store 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.