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Our top choices for Chester hotels

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
This charming B&B offers free WiFi and parking with a daily buffet breakfast. Outdoor enthusiasts will love the nearby hiking trails and mountain biking, while popular attractions like Bonnie's Bundles Dolls are just minutes away.

"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is NZ$390
includes taxes & fees
29 Dec - 30 Dec
Stone Hearth Inn and Eatery

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (403)
Experience small-town allure at this Chester inn with free breakfast, WiFi, and parking. Grab a drink at the bar, dine at the restaurant, and explore nearby DaVallia Art and Bonnie's Bundles Dolls. Guests rave about the clean rooms and helpful staff.

"Lovely stay"
United States
Christine
The price is NZ$241
includes taxes & fees
5 Jan - 6 Jan 2026
Fullerton Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (5)
"This was the perfect little getaway! Beautiful area, staff was nice, atmosphere was relaxing and having the hot tub option was perfect! "
United States
Harley
The price is NZ$248
includes taxes & fees
5 Jan - 6 Jan 2026
Hideaway Inn Mt. Snow

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1001)
This hotel offers quiet rooms and a peaceful environment near the Ashuelot River. Enjoy complimentary breakfast, WiFi, and parking. Guests love the helpful staff and convenient location. Visit the 24-hour fitness centre or unwind with a drink at the bar after exploring nearby attractions.

"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is NZ$258
includes taxes & fees
1 Jan - 2 Jan 2026
Best Western Plus Keene Hotel

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
This inviting Perkinsville inn offers free Wi-Fi, breakfast and parking. Unwind with drinks at the bar/lounge or savour a meal at the restaurant. North Springfield Lake and Stoughton Pond Recreation Areas await nearby.

"The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. "
United States
Joshua
The Inn at Weathersfield

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1001)
"The room was okay for a quick stop to rest. "
United States
Janice
The Putney Inn

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (968)
Escape to this quiet retreat with an indoor pool and fitness centre near Ashuelot River. Just minutes from local shops and eateries, this hotel offers free breakfast, WiFi, and parking. The helpful staff ensures a comfortable stay for business or leisure travellers.

"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is NZ$231
includes taxes & fees
28 Dec - 29 Dec
Keene Elm City Hotel, an Ascend Collection Hotel

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (613)
This Manchester Centre hotel offers a seasonal outdoor pool and free bike rentals to explore nearby hiking trails. Just minutes from Bromley Mountain for skiing enthusiasts, with complimentary WiFi and parking. Guests praise the helpful staff and clean, comfortable rooms.

"Super clean and modern rooms, excellent location, scenic views… "
United States
Fernando
The price is NZ$206
includes taxes & fees
13 Jan - 14 Jan 2026
Aspen At Manchester

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1003)
Step into comfort at this Manchester Centre hotel, just minutes from shopping destinations. The indoor pool and spa pool offer year-round relaxation, while rooms include convenient refrigerators and microwaves. Enjoy complimentary breakfast, WiFi, and parking before exploring nearby attractions.

"Great time "
United States
Paul
The price is NZ$246
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn and Suites Manchester

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
The price is NZ$335
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield Inn & Suites by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1002)
Stylish accommodation in Keene City centre, close to Colonial Theatre and Central Square. Enjoy a refreshing swim in the indoor pool, grab a bite at the coffee shop, then unwind at the bar. Free WiFi and parking make exploring the area convenient.

"Very comfortable and clean."
United States
Christina
The price is NZ$335
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Keene Downtown

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (71)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is NZ$424
includes taxes & fees
3 Jan - 4 Jan 2026
The Inn At Quail Run

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (782)
Surrounded by Green Mountains, this Manchester Centre hotel offers a seasonal outdoor pool and free breakfast. Hike nearby trails or enjoy skiing at Bromley Mountain. Spacious rooms provide comfort after exploring Dana L. Thompson Memorial Park.

"Staff and room was clean "
United States
Melissa
The Manchester View

Brook Bound Inn

Brook Bound Inn
2.0 star property
Wilmington
9.6 out of 10, Exceptional, (11)
Brook Bound Inn offers a charming Vermont retreat just minutes from Mount Snow. Enjoy snowmobiling on-site, then relax in the seasonal outdoor pool. With free WiFi and parking, this golf hotel puts North Branch Deerfield River adventures within easy reach.

"Great property. Amazing views!"
United States
Ryan
Brook Bound Inn

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
Manchester Center
8.4 out of 10, Very good, (866)
Surrounded by Vermont's natural beauty, this Manchester Centre hotel offers a golf course minutes from Bromley Mountain Ski Resort. Guests enjoy the spa pool, American dining at Clove + Maple, and complimentary breakfast while exploring nearby Lye Brook Falls.

"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
United States
Amanda
The price is NZ$219
includes taxes & fees
19 Jan - 20 Jan 2026
The Palmer House Resort, an Ascend Collection Hotel

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1001)
Located in Brattleboro, this motel offers American cuisine at India Masala House restaurant and a welcoming bar. Comfortable rooms include refrigerators and microwaves, while the spa provides relaxing massage treatments near Brattleboro Bowl.

"Nice place to stay for the night."
United States
Robin
The price is NZ$226
includes taxes & fees
29 Dec - 30 Dec
Colonial Motel And Spa

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (746)
Located minutes from Brattleboro Station, this welcoming hotel offers free breakfast, WiFi, and parking. Work out in the fitness centre before dining at the on-site restaurant. United States Navy Seabee Bridge and Brattleboro Bowl are nearby.

"Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!"
United States
Jack
The price is NZ$226
includes taxes & fees
31 Dec - 1 Jan 2026
Comfort Inn & Suites Brattleboro I-91

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (928)
Located minutes from Brattleboro Station, this welcoming hotel offers a relaxing spa pool and fitness centre for unwinding after exploring. Enjoy the complimentary breakfast before visiting nearby United States Navy Seabee Bridge or grabbing coffee at the café.

"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is NZ$277
includes taxes & fees
3 Jan - 4 Jan 2026
Hampton Inn Brattleboro

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (359)
Free breakfast, parking, and 24-hour fitness centre make this Keene hotel a great choice. Swim in the indoor pool or request room service after exploring nearby Cheshire Children's Museum. Travellers praise the helpful staff and morning meal.

"Clean comfy nice staff "
United States
Katherine
The price is NZ$308
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn & Suites Keene

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1001)
Set in Brattleboro, this charming inn sits near hiking trails and winter sports activities. Enjoy free continental breakfast each morning, complimentary WiFi, and parking. The United States Navy Seabee Bridge and Brattleboro Bowl are just minutes away.

"Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street. "
United States
Megan
The price is NZ$147
includes taxes & fees
28 Dec - 29 Dec
The Covered Bridge Inn
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.
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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?
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This holiday home rental outside of Chester is located on the waterfront, and has a balcony, a garden 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. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. 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 Bonnie's Bundles Dolls and DaVallia Art & Accents 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. Pointe at Castle Hill Resort and Grand Summit Resort, A Vail Resorts Property 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. A top sight in the area is Stratton Mountain Resort. 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. Additionally, you'll find Stratton Mountain Resort 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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