Search Chester hotels

  • 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

Our top choices for Chester hotels

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (434 reviews)
"The staff were incredible and the property have the perfect vibes for a ski trip. The food was great and everything was very clean and comfy."
United States
Rob
The price is NZ$236
includes taxes & fees
25 May - 26 May
Fullerton Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (118 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is NZ$340
includes taxes & fees
14 May - 15 May
Stone Hearth Inn and Eatery

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,000 reviews)
"We love staying here. It’s very clean, staff is always friendly,and the breakfast choices are great!!"
United States
Jennifer
The price is NZ$280
includes taxes & fees
26 May - 27 May
Best Western Plus Keene Hotel

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (856 reviews)
"Location and amenities were great and so was breakfast "
United States
Adina
The price is NZ$314
includes taxes & fees
1 June - 2 June
Best Western Springfield Hotel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,000 reviews)
"Easy access off the highway close enough to town for a meal or groceries "
United States
Kathleen
The price is NZ$174
includes taxes & fees
17 May - 18 May
The Putney Inn

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (973 reviews)
"Clean room, great included breakfast, staff was nice and overall was just a good time"
United States
Savanna
The price is NZ$234
includes taxes & fees
7 June - 8 June
Hampton Inn Brattleboro

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
"Great stay "
United States
Rashida
The price is NZ$255
includes taxes & fees
27 May - 28 May
Keene Elm City Hotel, an Ascend Collection Hotel

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)
"The girl at the front desk was very helpful and made our stay very pleasant."
United States
Brenda
The price is NZ$297
includes taxes & fees
17 May - 18 May
Hampton Inn and Suites Manchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,005 reviews)
"Great breakfast, friendly staff and good place to stay."
United States
Michael
The price is NZ$190
includes taxes & fees
14 May - 15 May
Days Inn by Wyndham Keene NH

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (803 reviews)
"Staff were friendly and the breakfast was very good, great selection of items to choose from 🙂"
United States
Desiree
The price is NZ$263
includes taxes & fees
1 June - 2 June
Comfort Inn & Suites Brattleboro I-91

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1,001 reviews)
"Excellent breakfast good parking safe atmosphere helpful staff and very clean overall "
United States
Danny
The price is NZ$331
includes taxes & fees
7 June - 8 June
Holiday Inn Express Hotel & Suites Brattleboro by IHG

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (387 reviews)
"Beautiful inn! Room exceeded expectations, tall ceilings, brickwork and river view!! Lots of cozy nooks throughout inn for board games, reading, etc. Breakfast options were excellent- fresh pastries, breakfast sandwiches and fruit. Highly recommend @"
United States
Sarah
The price is NZ$284
includes taxes & fees
21 May - 22 May
The Common Man Inn & Restaurant

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (993 reviews)
"Amazing hotel"
United States
Luis
The price is NZ$264
includes taxes & fees
28 May - 29 May
The Black Bear Lodge at Stratton Mountain Resort

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (772 reviews)
"Great hotel for a weekend getaway. Very walkable neighborhood too!"
United States
Stacey
The price is NZ$327
includes taxes & fees
31 May - 1 June
Fairfield Inn & Suites by Marriott Keene Downtown

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (499 reviews)
"Convenient location and friendly staff."
United States
Robert
The price is NZ$168
includes taxes & fees
14 May - 15 May
Claremont Motor Lodge

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is NZ$308
includes taxes & fees
25 May - 26 May
The Carriage Barn Inn

Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (545 reviews)
"Clean room, friendly staff. "
United States
Ken
The price is NZ$201
includes taxes & fees
14 May - 15 May
Four Winds Country Motel

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (385 reviews)
"Clean rooms, good location, easy parking, excellent service!"
United States
Kerry
The price is NZ$362
includes taxes & fees
7 June - 8 June
Hampton Inn & Suites Keene

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (441 reviews)
"We had an enjoyable stay and would stay again. "
United States
Donna
The price is NZ$155
includes taxes & fees
19 May - 20 May
Bromley View Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (491 reviews)
"Small place. Retro style. Nice for a stop over. Clean room. Felt safe. Super helpful staff. "
United States
Grace
The price is NZ$233
includes taxes & fees
14 May - 15 May
Black Mountain 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.
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?
Based on our traveller data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. Other good choices for your stay in the area are Woodstock Inn & Resort and Pointe at Castle Hill Resort. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Mountainside 5-BR Ski-In/Out Okemo Villa: This holiday home rental outside of Chester is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 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 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 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. Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains 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: Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. Pointe at Castle Hill Resort 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 66 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 The Nature Museum 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