Chester hotels from HK$614

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Our top choices for Chester hotels

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.0 out of 10, Very good, (424 reviews)
"Gorgeous old Inn that is fairly well maintained to keep up with modern competition. We visited in the dead of winter so the quaint town of Chester, VT didn’t have a lot to offer. We plan on visiting again in the summer to get the full experience!"
United States
William
The price is HK$1,010
HK$1,101 total
includes taxes & fees
2 Apr - 3 Apr
Fullerton Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (115 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is HK$1,441
HK$1,570 total
includes taxes & fees
26 Mar - 27 Mar
Stone Hearth Inn and Eatery

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (434 reviews)
"Great place to stay. I really loved the place."
United States
Simon
Bromley View Inn

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (340 reviews)
"Check-in was easy and the property is cute and very clean. "
United States
Karin
The price is HK$587
HK$646 total
includes taxes & fees
31 Mar - 1 Apr
Brittany Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (560 reviews)
"A great place to stay with pets. Rooms are a little tight, but they are clean and comfortable."
United States
Ron
Sleep Woodstock Motel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,000 reviews)
"Great Stay!"
United States
Nicholas
The Putney Inn

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (786 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is HK$1,101
HK$1,211 total
includes taxes & fees
28 Mar - 29 Mar
Comfort Inn & Suites Brattleboro I-91

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,005 reviews)
"Clean room, quiet, good price "
United States
Derek
The price is HK$558
HK$614 total
includes taxes & fees
31 Mar - 1 Apr
The Covered Bridge Inn

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, (999 reviews)
"Clean room, polite staff,kids enjoyed the indoor heated pool they also have a small gym and breakfast in the morning couldn't beat the price definitely a great place for the family dogs are also welcome!!"
United States
Sean
The price is HK$986
HK$1,070 total
includes taxes & fees
14 Apr - 15 Apr
Keene Elm City Hotel, an Ascend Collection Hotel

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (170 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is HK$936
HK$1,016 total
includes taxes & fees
2 Apr - 3 Apr
The Carriage Barn Inn

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (159 reviews)
"Clean room nicely, appointed easy access to a welcoming lobby in the most gentle piano music playing in the parlor"
United States
Shannon
The Burrell House

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (844 reviews)
"Very friendly staff. The room and all surroundings were clean and fresh smelling."
United States
Alison
The price is HK$1,191
HK$1,310 total
includes taxes & fees
13 Apr - 14 Apr
Best Western Springfield Hotel

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (954 reviews)
"I wish I could have stayed longer. Very nice hotel "
United States
Rosa
The price is HK$1,021
HK$1,123 total
includes taxes & fees
31 Mar - 1 Apr
Hampton Inn Brattleboro

Chalet 239

Chalet 239
2.0 star property
West Dover
9.4 out of 10, Exceptional, (118 reviews)
"The room was clean and staff were kind and friendly. "
United States
Sung
The price is HK$963
HK$1,060 total
includes taxes & fees
2 Apr - 3 Apr
Chalet 239

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)
"Great stay pool was very nice"
United States
Patrick
The price is HK$1,167
HK$1,267 total
includes taxes & fees
26 Mar - 27 Mar
Best Western Plus Keene Hotel

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (488 reviews)
"This is a pet friendly hotel when we told the front desk there were loud dogs they immediately spoke to owners and moved our room Clean rooms and excellent. Firm mattress would def go back"
United States
Rita
The price is HK$705
HK$776 total
includes taxes & fees
26 Mar - 27 Mar
Black Mountain Inn

Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (486 reviews)
"Nice and clean newly renovated room. Just what we needed for a good nights rest. "
United States
Valerie
The price is HK$791
HK$858 total
includes taxes & fees
26 Mar - 27 Mar
Claremont Motor Lodge

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (349 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is HK$1,122
HK$1,235 total
includes taxes & fees
31 Mar - 1 Apr
Colonel Williams Inn

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.6 out of 10, Excellent, (65 reviews)
"Very pleasant and comfortable stay, about 20 mins drive to Killington nearby. Room was clean and quiet, and bed was very comfortable. Nice coffee/hot chocolate bar in the lobby but unfortunately not offering breakfast anymore."
United States
Andrew
The price is HK$1,215
HK$1,337 total
includes taxes & fees
26 Mar - 27 Mar
Lincoln Inn & Gallery

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
8.6 out of 10, Excellent, (77 reviews)
"Clean cozy rooms, overall good stay"
United States
Wade
The price is HK$765
HK$842 total
includes taxes & fees
19 Apr - 20 Apr
Hideaway Inn Mt. Snow
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Where to stay in Chester

Find the best Chester areas for the activities you enjoy most. Learn more about Chester
Learn more about Chester

Chester Depot

If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

Stay near popular Chester attractions

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

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

Top Chester Hotel Reviews

More cheap stays in Chester

Find out more about Chester

Top reasons to visit Chester

  • Thrilling Skiing: Chester is perfect for skiing enthusiasts, offering local ski resorts and fields for winter sports adventures.
  • Vibrant Arts Scene: Explore Chester's rich arts culture through various galleries showcasing local talent.
  • Beautiful Parks: Enjoy the stunning natural beauty of parks and nearby state parks, ideal for outdoor activities.
  • Family-Friendly Attractions: Engage in animal shows and agricultural exhibits, ensuring fun for visitors of all ages.
  • Charming Accommodations: Choose from cosy bed and breakfasts and agritourism properties catering to all budgets.

Find great hotels near Chester

Discover a range of charming accommodations in Chester, Vermont, ideal for every type of traveller. From cosy bed and breakfasts to inviting agritourism properties, you’ll find affordable options that cater to families and adventure seekers alike. Many of these lodgings offer air conditioning, complimentary American breakfast, and spacious suites, making your stay both comfortable and memorable.

  • Best Western Springfield Hotel: Embrace a pet-friendly retreat at Best Western Springfield Hotel, located a mere 12.9km from Chester. This welcoming lodging is perfect for travellers seeking a hassle-free vacation with their furry companions. The hotel allows pets, with policies that ensure a comfortable stay for all. Guests appreciate the friendly atmosphere and essential amenities, making it an ideal base for exploring the charming surroundings of Vermont.
  • Pointe at Castle Hill Resort: Experience a blend of adventure and relaxation at Pointe at Castle Hill Resort, situated 14.5km away from Chester. This 3.5-star hotel caters to those with a thirst for outdoor activities and wellness. Guests can indulge in a variety of adventure sports, from hiking and biking to snow tubing and skiing. The property boasts a full-service spa, complete with a sauna and hot stone massages, ensuring a rejuvenating escape after an exciting day. Perfect for business travellers and adventure seekers alike, this resort offers a unique getaway in a stunning natural setting.
  • Jackson Gore Village: Discover the ideal mix of adventure and leisure at Jackson Gore Village, located 20.9km from Chester. This 3-star hotel is a haven for golf enthusiasts and those seeking a diverse range of outdoor activities. With options for mountain biking, hiking, and even ziplining, guests are never short of excitement. The full spa and indoor pool provide a tranquil retreat after a day of adventure, featuring services such as Swedish massages and a hot tub for ultimate relaxation. Jackson Gore Village offers a vibrant community atmosphere, making it a fantastic choice for families and groups.

Where to stay near Chester

Chester, Vermont, offers a delightful escape for tourists seeking adventure and relaxation. Surrounded by stunning autumn foliage, this charming town boasts a friendly atmosphere and various activities, from skiing to exploring historical sites. Nearby regions further enhance your experience with luxurious accommodations and budget-friendly options, allowing you to celebrate nature in style. Whether you're looking for a tranquil retreat or an exciting getaway, Chester promises unforgettable memories amidst its picturesque landscapes.

  • Rockingham: Nestled a mere 11.3km from Chester, Rockingham is a charming village that offers a blend of outdoor adventure and historical allure. This destination is particularly popular among travellers seeking skiing experiences, with nearby ski fields and resorts drawing visitors during the peak months of July to September. The area is also home to picturesque lakes, an esteemed historic college, and serene parks, making it an ideal spot for those who relish nature and exploration. Whether you're hitting the slopes or enjoying a leisurely stroll by the lake, Rockingham promises a delightful experience.
  • Londonderry: Located 17.7km from Chester, Londonderry is a vibrant city that attracts visitors year-round, especially in January, July, and September. Known for its thrilling skiing opportunities, this city boasts excellent ski resorts and fields that cater to both novices and seasoned skiers. Surrounded by stunning landscapes, including lakes, majestic mountains, and lush valleys, Londonderry is perfect for outdoor enthusiasts. The combination of adventure sports and scenic beauty makes this city a must-visit for those looking to immerse themselves in Vermont's natural wonders.
  • Charlestown: Just 14.5km from Chester, Charlestown is a city that beckons nature lovers and adventure seekers alike. With a moderate seasonal influx of visitors, peaking from July to September, Charlestown offers a wealth of outdoor activities, including skiing and hiking. Its proximity to breathtaking lakes, towering mountains, and a national state park provides ample opportunities for exploration and scenic enjoyment. The charming atmosphere and the beauty of the surrounding landscape ensure that every visitor leaves with unforgettable memories.

Things to do near Chester

Chester, Vermont, offers a delightful mix of activities for adventure seekers and sports enthusiasts. Visitors can enjoy skiing at local ski resorts and fields, while also exploring the vibrant arts scene through galleries. Don't miss the chance to partake in animal shows and agricultural exhibits, or embark on scenic day trips to fully experience the charm of this picturesque town.

Shopping

For delightful shopping in Chester, visit the Vermont Country Store and My Minds Design, both located 9.7km away. If you're up for a drive, the West River Farmers Market, situated 17.7km away, offers a vibrant public market experience with a local flair.

Recreation

At Hooper Golf Club, enjoy a round of golf surrounded by picturesque landscapes, just 25.7km from Chester, offering an invigorating outdoor experience. Crown Point Golf Course, located 12.9km away, also provides a vibrant sports atmosphere. For relaxation, visit The Ice House Ice Skating, 20.9km from Chester, where wellness takes centre stage.

Adventure

Okemo Mountain Resort, located 17.7km from Chester, offers exhilarating skiing experiences on its diverse slopes, perfect for both beginners and experts. Meanwhile, Magic Mountain Ski Resort, 16.1km away, boasts thrilling runs and a vibrant sports atmosphere, ideal for an adrenaline-filled day on the snow.

For a unique adventure, the Solitude Express Ski Lift, situated 19.3km from Chester, provides breathtaking views as you ascend to explore the expansive terrain, combining the thrill of skiing with the beauty of the surrounding landscape.

Nightlife

Experience a vibrant evening in Chester with a visit to the Weston Playhouse, offering captivating performances just 16.1km away. For a thrill, venture to Maple Lanes, an exciting arcade 22.5km away, or enjoy the Timber Ripper Mountain Coaster, located 20.9km away, for a memorable adventure.

*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 off-peak months of April to May and November when accommodation prices are lower. Aim to book your stay on a Tuesday for the best rates. Utilise Expedia's search tool to filter for eco-certified hotels and arrange results by price from lowest to highest. For additional savings, consider booking a package that combines your hotel, flights, and activities. Don't forget to check for app deals and compare prices to find the best options available.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are April to May and November, where the prices are slightly lower. This is in comparison to January to February and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Friday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels currently available. To find the most affordable prices and offers, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Chester with your flights and activities by booking a package through Expedia.

Find the best attractions near Chester

Chester, Vermont, is an ideal destination for those seeking ski and adventure sports holidays. This charming town offers a variety of attractions, including beautiful parks, the nearby state park, and fascinating history museums. Visitors can immerse themselves in outdoor activities, cultural experiences, and family-friendly adventures that cater to all interests. Whether you're skiing down the slopes or exploring the local heritage, Chester promises an enjoyable getaway for every traveller.

  • Fletcher Farm School for the Arts and Crafts: This unique educational institution, located 16.1km from Chester, offers a rich cultural experience. Visitors can engage in various arts and crafts workshops, perfect for unleashing creativity and learning new skills in a picturesque setting.
  • Buttermilk Falls: Situated 22.5km away, Buttermilk Falls is a stunning waterfall surrounded by nature, providing a romantic and adventurous atmosphere. It's an ideal spot for hiking, picnicking, and enjoying the beauty of Vermont's outdoors.
  • Vermont Museum of Mining and Minerals: Located just 9.7km from Chester, this family-friendly natural history museum showcases fascinating exhibits on mining and minerals, offering a cultural insight into Vermont’s geological heritage.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.7°F (-6.3°C)Light RainMostly CloudySlightly LowSlightly High
February22.6°F (-5.2°C)Light RainMostly CloudySlightly LowSlightly High
March30.7°F (-0.7°C)Light RainMostly CloudySlightly LowAverage
April42.8°F (6.0°C)Light RainMostly CloudyAverageSlightly Low
May55.8°F (13.2°C)Light RainMostly SunnyAverageSlightly Low
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnySlightly HighAverage
August67.3°F (19.6°C)Light RainMostly SunnySlightly HighAverage
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
October48.6°F (9.2°C)Light RainMostly SunnyAverageSlightly High
November36.1°F (2.3°C)Light RainMostly SunnyAverageSlightly Low
December27.3°F (-2.6°C)Light RainMostly CloudyAverageAverage

The nearest major airports for your trip to Chester

Chester, Vermont, is conveniently accessible via several major airports. Glens Falls, NY (GFL-Floyd Bennett Memorial) is situated 82.1km away, with nearby accommodation options like the 4-star Lodges At Cresthaven and the 3.5-star Six Flags Great Escape Lodge & Indoor Waterpark. Lebanon, NH (LEB-Lebanon Municipal) is a mere 46.7km from Chester, offering the 4-star Hanover Inn Dartmouth and the charming Windsor Mansion Inn. The nearest airport is Rutland, VT (RUT-Rutland Southern Vermont Regional), located 40.2km away, where you can find options such as the Killington Mountain Lodge, a 3.5-star hotel. Transport services are readily available from these hotels to their respective airports.

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?
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: 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 12 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. 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?
Pointe at Castle Hill Resort: Offers a full-service spa, an indoor pool and free self parking. Woodstock Inn & Resort and Hideaway Inn Mt. Snow 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 69 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 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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