Search Chester hotels

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

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Chester

Fullerton Inn

2.5 star property
Chester Depot
8.2 out of 10, Very good, (401)
"A unique inn in a charming town. Breakfast falls short, but staff is friendly and helpful "
United States
Dominique
The price is NZ$249
includes taxes & fees
13 Nov - 14 Nov
Fullerton Inn

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Room was super quiet and clean. "
United States
Ernest
The price is NZ$403
includes taxes & fees
19 Nov - 20 Nov
Stone Hearth Inn and Eatery

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (548)
"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 NZ$718
includes taxes & fees
30 Nov - 1 Dec
Woodstock Inn & Resort

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (881)
"Upon entering the hotel, the lobby is gorgeous with 2 fireplaces. Staff was super friendly and the free breakfast was a bonus. The room was spotless and has a fireplace in the room. My wife and I loved this place and will definitely go back. "
United States
Vincent
The Shire Woodstock

Aspen At Manchester

2.5 star property
Manchester Center
8.8 out of 10, Excellent, (599)
"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 NZ$226
includes taxes & fees
9 Dec - 10 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 NZ$279
includes taxes & fees
18 Nov - 19 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 NZ$226
includes taxes & fees
2 Dec - 3 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, (1000)
"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 NZ$247
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, (933)
"Great place for the price "
United States
Karen
The price is NZ$281
includes taxes & fees
24 Nov - 25 Nov
The Black Bear Lodge at Stratton Mountain Resort

The Covered Bridge Inn

2.5 star property
Brattleboro
7.6 out of 10, Good, (1000)
"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 NZ$160
includes taxes & fees
13 Nov - 14 Nov
The Covered Bridge Inn

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 NZ$377
includes taxes & fees
1 Dec - 2 Dec
Kimpton Taconic Hotel by IHG

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very good, (1000)
"Hotel was great."
United States
Heidi
The price is NZ$278
includes taxes & fees
13 Nov - 14 Nov
Best Western Plus Keene Hotel

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (567)
"Nice old Inn!"
United States
Daniel
The price is NZ$308
includes taxes & fees
19 Nov - 20 Nov
The Equinox Golf Resort & Spa

Pointe at Castle Hill Resort

3.5 star property
Cavendish
8.8 out of 10, Excellent, (917)
"Clean room, great staff, wonderful suggestions for area restaurants and attractions."
United States
Margie
The price is NZ$260
includes taxes & fees
13 Nov - 14 Nov
Pointe at Castle Hill Resort

Days Inn by Wyndham Keene NH

2.0 star property
Keene
7.0 out of 10, Good, (1000)
"Great stay"
United States
Michael
The price is NZ$212
includes taxes & fees
8 Dec - 9 Dec
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, (1003)
"Friendly, efficient staff and a very clean and nice room"
United States
Margaret
The price is NZ$261
includes taxes & fees
30 Nov - 1 Dec
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, (625)
"Loved my stay"
United States
Christine
The price is NZ$292
includes taxes & fees
11 Dec - 12 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 NZ$488
includes taxes & fees
24 Nov - 25 Nov
Vantage Point Villas at Stratton Mountain Resort

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
Brownsville
9.0 out of 10, Wonderful, (773)
"Strongly recommend and will go back again!"
Canada
Craig
The price is NZ$273
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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

Our guide on 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 accommodation in Chester

Find out more about Chester

Top reasons to visit Chester

  • Thrilling Ski Adventures: Experience world-class skiing in the nearby Green Mountains, perfect for adventure seekers.
  • Charming Local Attractions: Explore family-friendly sites, including a local zoo and historical cathedral.
  • Scenic Outdoor Activities: Enjoy various parks and outdoor experiences amidst stunning natural beauty.
  • Unique Accommodation Options: Choose from inviting bed and breakfasts and agritourism properties for a cosy stay.
  • Vibrant Community Atmosphere: Immerse yourself in the friendly neighbourhoods and warm hospitality of Chester.

Find great hotels near Chester

Explore the charming town of Chester, Vermont, where you'll find a range of delightful accommodation options to suit every traveller's needs. From inviting bed and breakfasts to unique agritourism properties, Chester offers family-friendly, adventure-filled, and pet-friendly lodging experiences. Discover the perfect place to unwind and enjoy the picturesque surroundings while indulging in the warm hospitality that makes this town a memorable destination.

  • Best Western Springfield Hotel: Located a mere 12.9km from Chester, the Best Western Springfield Hotel offers a welcoming environment for pet lovers. With a pet-friendly policy, you can bring your furry companions along for the adventure. The hotel features essential amenities to ensure a comfortable stay, including service animals allowed without fees. Enjoy the convenience of a well-appointed lodging experience that caters to both leisure and business travellers, making it a versatile choice for all visitors.
  • Pointe at Castle Hill Resort: Situated 14.5km from Chester, the Pointe at Castle Hill Resort is a 3.5-star gem perfect for those seeking a blend of relaxation and adventure. The resort is equipped with a full-service spa offering rejuvenating treatments like hot stone massages and aromatherapy, alongside an array of business facilities including multiple meeting rooms and an accessible business centre. For the adventurous, options abound with nearby activities such as horse riding, snowshoeing, rafting, and fishing, making this a prime location for both business and leisure.
  • Jackson Gore Village: Just 20.9km from Chester, Jackson Gore Village is a delightful 3-star accommodation designed for ski enthusiasts and adventure seekers. Guests can easily access ski shuttles and lifts, making it a convenient base for winter sports. Onsite activities include snowboarding, ziplining, and snow tubing. The village also features a comprehensive spa and wellness centre, offering services such as deep tissue massages and hot tub access, ensuring a relaxing retreat after a day of exhilarating outdoor activities.

Where to stay near Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation for every traveller. Experience the thrill of skiing in the nearby Green Mountains or unwind in charming holiday cottages that reflect the region's historical vibe. Explore the friendly atmosphere of local neighbourhoods while soaking in stunning city views. Whether you seek luxury or budget-friendly options, Chester promises a memorable getaway filled with unique experiences and warm hospitality.

  • Ludlow: Situated 17.7km from Chester, Ludlow is a lively city that attracts visitors year-round, with peak traffic during the winter months. Known for its outdoor adventures, Ludlow is a haven for skiing enthusiasts, boasting excellent ski fields and resorts. In addition to winter sports, the surrounding landscape features stunning lakes, majestic mountains, and picturesque valleys, making it a perfect destination for both thrill-seekers and nature lovers. Whether you’re hitting the slopes or enjoying a scenic hike, Ludlow promises an exhilarating travel experience.
  • Springfield: Located a mere 9.7km from Chester, Springfield is a vibrant city that welcomes visitors throughout the year, with notable peaks in February, July, and September. The city is popular among adventure seekers, particularly for skiing, with its close proximity to ski fields and resorts. Beyond winter sports, Springfield is home to beautiful lakes and mountains, as well as a national state park, offering numerous outdoor activities and opportunities for exploration. This blend of adventure and natural beauty makes Springfield a must-visit on your journey.
  • Grafton: Just 9.7km from Chester, Grafton is a charming city where visitors can enjoy a variety of experiences year-round, especially during the summer and autumn months. Known for its outdoor adventures, Grafton is an excellent base for skiing, with access to superb ski fields and resorts. The scenic surroundings include stunning valleys, lakes, and mountains, perfect for hiking, biking, or simply soaking in the breathtaking views. Grafton’s combination of adventure and tranquil landscapes ensures a memorable getaway.

Things to do near Chester

Chester, Vermont, is perfect for adventure seekers and ski enthusiasts alike. Enjoy thrilling activities such as skiing at local resorts, exploring family attractions, and witnessing enchanting light shows. Discover the charm of Chester as you delve into its vibrant offerings, making it an ideal destination for a memorable vacation filled with outdoor fun and exploration.

Shopping

In Chester, you can explore the Vermont Country Store and My Minds Design, both located 9.7km away, offering unique gifts and souvenirs. If you're up for a drive, check out the West River Farmers Market, situated 17.7km from Chester, for a lively local shopping experience.

Recreation

Enjoy a round of golf at Crown Point Golf Course, surrounded by beautiful landscapes and outdoor vibes, or visit Fox Run Golf Course for another scenic golfing experience. For relaxation, head to The Ice House Ice Skating, where you can unwind and enjoy the serene atmosphere.

Adventure

Okemo Mountain Resort, 17.7km from Chester, offers thrilling skiing experiences amidst stunning snow-covered landscapes. For a unique adventure, Morningside Flight Park, located 19.3km away, provides breathtaking scenic flights over picturesque vistas. Don't miss the Solitude Express Ski Lift, also 19.3km from Chester, for an exhilarating ascent on the slopes.

Nightlife

In Chester, the Weston Playhouse offers a charming theatre experience just 16.1km away, perfect for a romantic night out. For thrills, the Timber Ripper Mountain Coaster and Maple Lanes arcade adventure zone, located 13 and 22.5km away respectively, provide exciting entertainment options for all ages.

*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, consider visiting during the cheaper months of April to May and November, with Tuesday being the most affordable day to stay. Use Expedia to compare accommodation options and sort by price to find the best deals. Combining your hotel booking with flights and activities can also help you save. Take advantage of free activities like hiking and exploring the local scenery, and consider using public transport or walking to get around town, as Chester is easy to navigate on foot.

  • 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, preferred location, and the type of accommodation you're looking for. To find the most affordable prices and special offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some dollars by combining your Chester hotel booking with flights and activities through an Expedia package. It's a great way to make the most of your travel budget.

Find the best attractions in and around Chester

Chester, Vermont, is a fantastic destination for skiing and adventure sports, offering a variety of attractions such as parks, state parks, and history museums. Visitors can immerse themselves in outdoor activities and cultural experiences that cater to families. Don't miss exploring the charming city of Chester, with its local zoo, historical cathedral, and vibrant racecourse, ensuring a memorable vacation filled with diverse experiences.

  • DaVallia Art & Accents: Immerse yourself in Chester's vibrant culture at this unique gallery, showcasing a variety of local artworks that reflect the area's creative spirit. It's a perfect spot to appreciate and perhaps purchase a piece of Vermont's artistic heritage.
  • Lowell Lake State Park: Experience adventure and stunning scenery just 14.5km from Chester. Whether you’re hiking, picnicking, or enjoying water activities, this park offers a fantastic outdoor experience surrounded by nature’s beauty.
  • Bonnie's Bundles Dolls: Step into a world of charm and nostalgia at this delightful attraction. Each doll tells a story, making it a romantic and whimsical stop for visitors of all ages, perfect for those seeking a unique souvenir.

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

For your visit to Chester, Vermont, you have several airport options. Lebanon Municipal Airport (LEB) is situated 46.7km away, with nearby accommodation such as the 4-star Hanover Inn Dartmouth, 8.0km from the airport, and the 3-star Hotel Coolidge, just 3.2km away. Rutland Southern Vermont Regional Airport (RUT) is 28.0km from Chester, with options like the 3.5-star Killington Grand Hotel, 16.1km away. The closest is Hartness State Airport (VSF) in Springfield, located 11.3km away, offering hotels like the 4-star Inn at Weathersfield, just 1.6km from the airport. Each airport provides convenient access to Chester and surrounding areas.

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.
What are some of the best holiday rentals that Chester has to offer?
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Chester is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday 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 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 family accommodation in 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. Also, attractions such as DaVallia Art & Accents and Bonnie's Bundles Dolls are fun for children of all ages. Find more child-friendly accommodations in Chester.
What's the best place to stay for a romantic holiday in Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favourite guest house for couples, and features free WiFi and a garden. See all romantic hotels 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. Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub is another option for a stay with your pet. 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. Jackson Gore Village and Kimpton Taconic Hotel by IHG 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 68 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.

Explore a world of travel with Expedia