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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, (115 reviews)
"So great all around!"
United States
Janet
The price is AU$298
includes taxes & fees
23 Mar - 24 Mar
Stone Hearth Inn and Eatery

Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (420 reviews)
"Great staff and service. "
United States
Chris
The price is AU$200
includes taxes & fees
10 Mar - 11 Mar
Fullerton Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
8.8 out of 10, Excellent, (68 reviews)
"Clean cozy rooms, overall good stay"
United States
Wade
The price is AU$211
includes taxes & fees
10 Mar - 11 Mar
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, (1,002 reviews)
"Great stay pool was very nice"
United States
Patrick
The price is AU$184
includes taxes & fees
10 Mar - 11 Mar
Best Western Plus Keene Hotel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,009 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
The Putney Inn

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (75 reviews)
"Everything was really lovely, clean and nice. Loved the downstairs lounge and bar areas, so warm and relaxing. The host was extremely gracious. Looking forward to going back soon! "
United States
James
The Inn at Weathersfield

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, (990 reviews)
"Staff were great place was clean and nice. "
United States
Alex
The price is AU$168
includes taxes & fees
10 Mar - 11 Mar
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, (1,008 reviews)
"Very clean hotel! "
United States
Robert
The price is AU$204
includes taxes & fees
22 Mar - 23 Mar
Hampton Inn and Suites Manchester

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, (766 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is AU$270
includes taxes & fees
17 Mar - 18 Mar
Fairfield Inn & Suites by Marriott Keene Downtown

Aspen At Manchester

Aspen At Manchester
2.5 star property
Manchester Center
8.8 out of 10, Excellent, (637 reviews)
"Super clean and modern rooms, excellent location, scenic views… "
United States
Fernando
The price is AU$181
includes taxes & fees
29 Mar - 30 Mar
Aspen At Manchester

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,004 reviews)
"Really clean hotel, friendly staff and great location."
United States
Aaron
The price is AU$278
includes taxes & fees
15 Mar - 16 Mar
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, (72 reviews)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is AU$352
includes taxes & fees
10 Mar - 11 Mar
The Inn At Quail Run

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (818 reviews)
"Great staff, huge clean room, tasty continental breakfast."
United States
Carey
The Manchester View

Brook Bound Inn

Brook Bound Inn
2.0 star property
Wilmington
9.2 out of 10, Wonderful, (16 reviews)
"Beautiful lodge very clean and comfortable "
United States
Virginia
Brook Bound Inn

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1,006 reviews)
"Clean, cozy , spacious, comfortable rooms, friendly staff, great area, excellent spa! "
United States
Ana
The price is AU$149
includes taxes & fees
10 Mar - 11 Mar
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, (781 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is AU$176
includes taxes & fees
15 Mar - 16 Mar
Comfort Inn & Suites Brattleboro I-91

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (948 reviews)
"Good breakfast, great staff and very good location "
United States
Valdeci
The price is AU$166
includes taxes & fees
16 Mar - 17 Mar
Hampton Inn Brattleboro

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (369 reviews)
"Clean, comfortable. "
United States
Jacklyn
The price is AU$257
includes taxes & fees
29 Mar - 30 Mar
Hampton Inn & Suites Keene

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,007 reviews)
"Easy check in and good parking"
United States
nicholas
The price is AU$98
includes taxes & fees
10 Mar - 11 Mar
The Covered Bridge Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (486 reviews)
"Instant check-in and check-out Very responsive and friendly staff. Clean and well maintained. Everything you need is provided. The room is spacious, and the beds are comfortable."
United States
Olga
The price is AU$165
includes taxes & fees
12 Mar - 13 Mar
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.

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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

Recent Reviews in Chester

More cheap accommodation in Chester

Find out more about Chester

Top reasons to visit Chester

  • Thrilling Skiing: Chester boasts excellent skiing opportunities at nearby ski fields and resorts, perfect for adventure lovers.
  • Scenic Outdoor Activities: Enjoy treasure hunts, picturesque golf courses, and the stunning Cheshire countryside for outdoor fun.
  • Charming Accommodation: Experience a mix of agritourism properties and delightful bed & breakfasts for a comfortable stay.
  • Rich Local Culture: Engage with friendly locals and explore historical sites, offering a glimpse into the area's heritage.
  • Family-Friendly Atmosphere: Chester caters to families with diverse activities, ensuring a memorable holiday for everyone.

Find great hotels near Chester

Discover the charming accommodation options in Chester, Vermont, where a mix of agritourism properties and delightful bed & breakfasts await. Perfect for families, adventure seekers, and pet lovers, Chester offers a welcoming atmosphere for all travellers. Whether you're searching for star-rated hotels or luxury stays, you'll find a variety of choices to suit your needs while enjoying the picturesque landscapes and local attractions.

  • Best Western Springfield Hotel: Located a mere 12.9km from Chester, Best Western Springfield Hotel is the perfect choice for pet-loving travellers seeking a welcoming atmosphere. This hotel allows pets on-site, making it an ideal spot for those who want to bring their furry friends along. With amenities that include a pet-friendly policy, guests can enjoy a hassle-free stay while indulging in the hotel’s comfortable accommodations and friendly service. A great base for exploring the surrounding areas, this hotel offers convenience and comfort.
  • Jackson Gore Village: Situated 20.9km from Chester, Jackson Gore Village is a family-oriented 3-star hotel that caters to adventure seekers and ski enthusiasts alike. With easy access to ski shuttles and lifts, this property is a winter wonderland for those keen on snow sports. On-site activities include snow tubing, a ropes course, and mini-golf, ensuring fun for all ages. Families can benefit from a range of child-friendly amenities such as a playground and arcade game room, making this a versatile choice for a memorable family vacation.
  • The Upper Pass Lodge at Magic Mountain: Nestled 16.1km from Chester, The Upper Pass Lodge at Magic Mountain is a charming motel that embraces adventure and pet-friendly experiences. With a variety of outdoor activities like cross-country skiing, snowboarding, and ziplining nearby, this lodge is perfect for thrill-seekers. Guests can relax knowing their pets are welcome too, as the property allows pets with a waived fee for service animals. This lodge promises a blend of adventure and comfort for an unforgettable getaway.

Where to stay near Chester

Chester, Vermont, offers a delightful mix of adventure and relaxation for travellers. Embrace the thrill of skiing and exploring the picturesque Cheshire countryside, while also enjoying the charming local atmosphere. Visit nearby historical sites, indulge in budget-friendly activities, or simply unwind in the serene surroundings. With friendly locals and captivating attractions, Chester promises a memorable escape for every kind of traveller.

  • Ludlow: Located approximately 17.7km from Chester, Ludlow is a charming city that comes alive in the winter months, drawing visitors for its exceptional skiing opportunities. With a vibrant ski culture, you'll find top-notch ski fields and resorts that cater to both beginners and seasoned adventurers. Beyond skiing, Ludlow is surrounded by stunning landscapes, including serene lakes and majestic mountains, making it a perfect spot for outdoor enthusiasts year-round. The local community is warm and welcoming, offering a variety of dining and shopping experiences that reflect the region’s character.
  • Springfield: Just 9.7km from Chester, Springfield is a delightful city that welcomes visitors throughout the year. The town is particularly popular during February, July, and September, when outdoor sports and activities thrive. Springfield is known for its skiing, with access to excellent ski resorts and fields. Nature lovers will appreciate the nearby national state park, offering numerous hiking trails and breathtaking views. The mix of adventure and leisure activities ensures that there’s something for everyone, whether you're seeking adrenaline-pumping experiences or a peaceful retreat in nature.
  • Grafton: Also located 9.7km from Chester, Grafton is a picturesque city that attracts visitors with its outdoor adventure offerings. Known for its skiing, this charming town is a gateway to ski fields and resorts that promise thrilling winter sports. Grafton's stunning landscapes, featuring rolling valleys and towering mountains, provide ample opportunities for hiking, biking, and enjoying the great outdoors. Peak visitor months are July and September to October, making it an ideal time to explore the natural beauty and local attractions that make Grafton a hidden gem in Vermont.

Things to do near Chester

Chester, Vermont, offers an exciting getaway for adventure lovers and families alike, featuring excellent skiing opportunities at local ski fields and resorts. Beyond the slopes, you can enjoy thrilling treasure hunts and explore scenic golf courses, making it a perfect destination for a memorable holiday. Whether you're hitting the powder or enjoying family-friendly activities, Chester has something for everyone to enjoy.

Shopping

In Chester, the Vermont Country Store and My Minds Design, both 9.7km away, offer charming local gifts. If you're up for a drive, the West River Farmers Market, located 17.7km from Chester, provides a vibrant atmosphere with fresh produce and unique crafts.

Recreation

Experience a round of golf at Crown Point Golf Course, surrounded by beautiful landscapes and outdoor vibes, only 12.9km from Chester. Alternatively, enjoy a relaxing skate at The Ice House Ice Skating, located 20.9km away, perfect for unwinding in a tranquil atmosphere.

Adventure

Hit the slopes at Magic Mountain Ski Resort, located 16.1km from Chester, for thrilling skiing experiences. For a different perspective, soar above the stunning landscapes at Morningside Flight Park, 19.3km away. Alternatively, enjoy the exhilarating ride on the Sachem Ski Lift, also 19.3km from Chester.

Nightlife

Experience the vibrant nightlife in Chester with a show at the Weston Playhouse, just 16.1km away, offering a mix of culture and romance. For a thrill, try the Timber Ripper Mountain Coaster, 20.9km away, or enjoy family fun at Maple Lanes, 22.5km away, for an arcade adventure!

Booking tips and Expedia advantages for Chester

For a budget-friendly trip to Chester, Vermont, consider visiting during the off-peak months of April to May and November for lower accommodation prices. Tuesdays typically offer the best rates, while Fridays are the priciest. Use Expedia's search tool to sort hotels by budget and filter for eco-friendly options. Combine hotel bookings with flights and activities for added savings. Take advantage of free local attractions and opt for public transport or consider renting a bicycle to explore the charming town without breaking the bank.

  • 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: Expedia's search tool lets you set your budget, choose your desired location, and much more. You can sort your results to display prices from lowest to highest, ensuring you find the most affordable accommodation first. Additionally, you have the option to narrow your choices by hotel type—for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are ready for booking.
  • Consider bundling your trip: You can save some cash by combining your Chester hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions in and around Chester

Chester, Vermont, is an ideal destination for ski and adventure holidays, offering stunning national parks, scenic mountains, and inviting parks. This charming town provides a plethora of outdoor activities and cultural experiences for families. While exploring the area, don't miss the chance to find the best hotels in Chester for a comfortable stay.

  • Lowell Lake State Park: Experience the great outdoors at this stunning state park, located 14.5km from Chester. Enjoy activities like hiking, fishing, and picnicking while surrounded by beautiful scenery and tranquil lake views, perfect for adventure enthusiasts.
  • DaVallia Art & Accents: Nestled in Chester, this charming gallery showcases local art and unique accents. Immerse yourself in the vibrant culture as you explore various artworks and crafts, making it a delightful stop for art lovers.
  • Vermont Museum of Mining and Minerals: Located 9.7km away, this fascinating museum offers a deep dive into the region's mining history. It's a great family-friendly attraction, featuring engaging exhibits that educate visitors of all ages.

Best time to go to Chester

The best time to visit Chester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

When visiting Chester, Vermont, you have several airport options. Lebanon Municipal Airport (LEB) is 46.7km away, with nearby hotels such as the 4-star Hanover Inn Dartmouth and the 3-star Hotel Coolidge. Rutland Southern Vermont Regional Airport (RUT) is slightly closer at 40.2km, with accommodation options like the Killington Mountain Lodge and Killington Grand Hotel, both rated 3.5 stars. For an even closer choice, Hartness State Airport (VSF) is only 11.3km from Chester, with the Castle Hill Resort and Spa as a notable 3.5-star option. All these airports provide convenient access to Chester, ensuring a pleasant arrival experience.

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 The Equinox Golf Resort & Spa 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 68 hotels and other accommodation options to choose from. Find out more about Chester.
What should I do while I'm visiting Chester?
A couple of favourite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. 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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