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Our top choices for Chester hotels

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (439 reviews)
"Beautiful old inn Great Staff"
United States
Elizabeth A
The price is NZ$288
includes taxes & fees
30 June - 1 July
Fullerton Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (120 reviews)
"Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
United States
Kathleen
The price is NZ$373
includes taxes & fees
9 July - 10 July
Stone Hearth Inn and Eatery

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, (1,003 reviews)
"Good stay everything you could ask for from a budget friendly hotel."
United States
Stephen
The price is NZ$209
includes taxes & fees
29 June - 30 June
Keene Elm City Hotel, an Ascend Collection Hotel

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (821 reviews)
"Perfectly comfortable and convenient for us, and the complimentary breakfast buffet was better than most!"
United States
Bonnie
The price is NZ$220
includes taxes & fees
2 July - 3 July
Comfort Inn & Suites Brattleboro I-91

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,005 reviews)
"Best place to stay the food was good and we had a wonderful stay. Swimming pool was fun and safe for kids"
United States
Nidia Ruby
The price is NZ$229
includes taxes & fees
29 June - 30 June
Best Western Plus Keene Hotel

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (1,001 reviews)
"Clean and professionally-run hotel - would stay again."
United States
Heidi
The price is NZ$223
includes taxes & fees
2 July - 3 July
Hampton Inn Brattleboro

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (449 reviews)
"The staff was very friendly and helpful."
Canada
Dumitru Florin
The price is NZ$170
includes taxes & fees
1 July - 2 July
Bromley View Inn

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (522 reviews)
"Great stay and good location"
Canada
Alexandre
The price is NZ$185
includes taxes & fees
28 June - 29 June
Claremont Motor Lodge

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (372 reviews)
"The bed was very comfortable! We had a great sleep and made our breakfast in the "snack room". It was pleasant and quiet- we sat on chairs out front looking at the mountain in front of us. It was a great place to stay."
United States
Susan
The price is NZ$168
includes taxes & fees
6 July - 7 July
Brittany Motel

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (171 reviews)
"Self check-in and checkout. Room was very clean but a bit too much potpourri for my allergies. Will stay here again when in Keene. "
United States
Charles
The price is NZ$262
includes taxes & fees
5 July - 6 July
The Burrell House

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (129 reviews)
"Staff very helpful. Everything was very clean"
United States
Patrick
The price is NZ$221
includes taxes & fees
8 July - 9 July
Chalet 239

The Landgrove

The Landgrove
3.5 star property
Londonderry
The price is NZ$308
includes taxes & fees
28 June - 29 June
The Landgrove

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
The price is NZ$307
includes taxes & fees
28 June - 29 June
Colonel Williams Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is NZ$341
includes taxes & fees
28 June - 29 June
The Carriage Barn Inn

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, (1,000 reviews)
"Breakfast was delicious!"
United States
Jean
The price is NZ$290
includes taxes & fees
2 July - 3 July
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (865 reviews)
"Great place to stay"
United States
Daniel
The price is NZ$349
includes taxes & fees
9 July - 10 July
Best Western Springfield Hotel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.6 out of 10, Excellent, (1,000 reviews)
"Perfect for an overnight!"
United States
Lori
The price is NZ$212
includes taxes & fees
29 June - 30 June
The Putney Inn

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (395 reviews)
"We have stayed at The Common Man Inn many times. It is always a treat. Right in town, very clean, restaurant is great and breakfast is perfect to start your day. The staff is very helpful and always available as well as friendly."
United States
Robert
The price is NZ$299
includes taxes & fees
13 July - 14 July
The Common Man Inn & Restaurant

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (43 reviews)
"The hot tub was so amazing"
United States
Mark
The price is NZ$237
includes taxes & fees
30 June - 1 July
Four Columns Inn

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
2.5 star property
Manchester Center
9.6 out of 10, Exceptional, (1,001 reviews)
"This was a great hotel. So fresh and clean and the staff was wonderful. "
United States
Kathryn
The price is NZ$254
includes taxes & fees
5 July - 6 July
Hampton Inn and Suites Manchester
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.

A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

Recent Reviews in Chester

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 Latchis Hotel. 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?
Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains is a top dog-friendly option for your stay. Motel in the Meadow 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. On The River Inn 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 62 hotels and other accommodation options to choose from. Find out more about Chester.
What should I do while I'm visiting Chester?
Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are fun for everyone. You'll also find Vermont Country Store and Lowell Lake State Park 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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