Find hotels in Chester, VT from AED 369

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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, (433 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 AED 474
AED 516 total
includes taxes & fees
12 May - 13 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 AED 698
AED 761 total
includes taxes & fees
21 May - 22 May
Stone Hearth Inn and Eatery

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 AED 293
AED 322 total
includes taxes & fees
11 May - 12 May
Bromley View Inn

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (352 reviews)
"I love this place! It’s funky and kind. Kept clean and just has a really inviting and sweet vibe."
United States
Andrew
The price is AED 275
AED 303 total
includes taxes & fees
11 May - 12 May
Brittany Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (578 reviews)
"Quiet, well kept, comfortable, convenient."
United States
Elisabeth
The price is AED 249
AED 483 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock Motel

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 AED 338
AED 367 total
includes taxes & fees
11 May - 12 May
Claremont Motor Lodge

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.8 out of 10, Excellent, (68 reviews)
"Peaceful, historic property with amiable keepers."
United States
Elisabeth
The price is AED 559
AED 615 total
includes taxes & fees
12 May - 13 May
Lincoln Inn & Gallery

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 AED 592
AED 651 total
includes taxes & fees
21 May - 22 May
Best Western Springfield Hotel

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (353 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is AED 532
AED 585 total
includes taxes & fees
12 May - 13 May
Colonel Williams Inn

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (972 reviews)
"Clean room, great included breakfast, staff was nice and overall was just a good time"
United States
Savanna
The price is AED 465
AED 512 total
includes taxes & fees
7 Jun - 8 Jun
Hampton Inn Brattleboro

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (38 reviews)
"The hot tub was so amazing"
United States
Mark
The price is AED 479
AED 522 total
includes taxes & fees
11 May - 12 May
Four Columns Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
8.8 out of 10, Excellent, (93 reviews)
"Newly renovated, clean, easy self check in, and great location!"
United States
Dana
The price is AED 373
AED 410 total
includes taxes & fees
10 Jun - 11 Jun
Hideaway Inn Mt. Snow

Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (180 reviews)
"Very comfortable room and nice staff. Will stay there again. "
United States
Laura
The price is AED 465
AED 506 total
includes taxes & fees
12 May - 13 May
Aerie Inn of Vermont

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 AED 716
AED 788 total
includes taxes & fees
12 May - 13 May
The Inn At Quail Run

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,004 reviews)
"Great breakfast, friendly staff and good place to stay."
United States
Michael
The price is AED 340
AED 369 total
includes taxes & fees
14 May - 15 May
Days Inn by Wyndham Keene NH

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (164 reviews)
"We had a wonderful stay at The Burrell House. The room was large, beautifully renovated with a well thought out design. It is a very short walk or drive to Main Street where there were a multitude of restaurants and shops. We truly enjoyed our stay and plan to book again soon. "
United States
Melissa
The price is AED 511
AED 570 total
includes taxes & fees
14 May - 15 May
The Burrell House

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (262 reviews)
"If you're planning a trip to bellows falls or the surrounding areas I would highly recommend the Harvest Barn Inn. The location is beauti"
United States
Gabriel
The price is AED 547
AED 596 total
includes taxes & fees
21 May - 22 May
Harvest Barn Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,003 reviews)
"Pleasant stay!"
United States
Steven
The price is AED 345
AED 380 total
includes taxes & fees
13 May - 14 May
The Putney Inn

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,008 reviews)
"The stay was great"
United States
Devon
The price is AED 566
AED 614 total
includes taxes & fees
11 May - 12 May
Best Western Plus Keene Hotel

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (17 reviews)
"Warm hospitality, very nice breakfast"
United States
Christopher
The price is AED 569
AED 618 total
includes taxes & fees
12 May - 13 May
Inn at Valley Farms
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Where to stay in Chester

Find the best Chester areas and neighborhoods 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 stays in Chester

Hotels in Chester with star-rating

Find out more about Chester

Top reasons to visit Chester

  • Outstanding Skiing Opportunities: Chester is a haven for ski enthusiasts with various local ski resorts offering thrilling winter sports.
  • Charming Local Shops: The town features quirky boutiques that provide a unique shopping experience, adding to Chester's charm.
  • Beautiful Parks and Nature: Visitors can explore stunning parks and state parks, perfect for outdoor adventures and family outings.
  • Rich Historical Sites: Chester boasts historical museums and sites, enriching your understanding of the local culture.
  • Diverse Lodging Options: From cozy B&Bs to unique agritourism stays, Chester offers accommodations for every type of traveler.

Find great hotels near Chester

Experience the charm of Chester, Vermont, with a variety of lodging options that cater to every traveler. From cozy bed & breakfasts to unique agritourism properties, you'll find accommodations perfect for family adventures or pet-friendly getaways. Explore Chester's hotels and inns, read reviews, and discover the perfect hotel rooms to make your stay memorable in this picturesque destination.

  • Best Western Springfield Hotel: Nestled 12.9km from Chester, Best Western Springfield Hotel is a welcoming retreat for pet owners and their furry friends. This hotel prides itself on providing a pet-friendly atmosphere, ensuring that your pets are treated with care. With amenities such as designated dog areas and a flexible pet policy, it caters to travelers looking for a comfortable stopover. The hotel features cozy accommodations, complimentary breakfast, and a fitness center, making it an ideal choice for families and those seeking a convenient base to explore the surrounding area.
  • Pointe at Castle Hill Resort: Located 14.5km from Chester, Pointe at Castle Hill Resort offers a luxurious escape for adventure enthusiasts and business travelers alike. This 3.5-star hotel features an array of exciting activities such as rafting, hiking, and skiing nearby, ensuring an action-packed stay. Guests can unwind at the full-service spa, which includes rejuvenating body wraps and facial treatments, or take a dip in the pool and hot tub. The resort's elegant accommodations and business facilities make it a perfect blend of relaxation and productivity, appealing to those who seek both adventure and comfort.
  • Jackson Gore Village: Situated 20.9km from Chester, Jackson Gore Village is an excellent choice for those who love skiing and golfing. This 3-star hotel offers direct access to ski lifts and shuttles, making it easy for guests to hit the slopes. With on-site amenities for snow tubing and snowshoeing, adventure is right at your doorstep. Golf enthusiasts will appreciate the nearby golfing opportunities, while comfortable accommodations provide a cozy retreat after a day of outdoor activities. Jackson Gore Village is perfect for families and groups looking for a fun-filled getaway.

Where to stay near Chester

Chester, Vermont, is a charming destination perfect for a weekend getaway, offering a mix of relaxation and adventure. Explore downtown Chester for its friendly atmosphere and historical sites, or head to nearby areas for skiing and outdoor sports. With various recreational opportunities, you can enjoy both budget-friendly and luxurious experiences. Whether you're seeking thrilling activities or a peaceful retreat, Chester has something for every traveler to enjoy.

  • Ludlow: Nestled 17.7km from Chester, Ludlow is a charming city known for its vibrant ski culture. Visitors flock here for thrilling winter sports and adventure activities, making it a popular destination from December to February. The ski fields and resorts are prime spots for both novices and seasoned skiers. In addition to winter sports, Ludlow's stunning natural landscapes, including lakes and mountains, provide the perfect backdrop for outdoor enthusiasts year-round.
  • Springfield: Located just 9.7km from Chester, Springfield offers a diverse travel experience with a mix of adventure and nature. The city attracts visitors throughout the year, with peak seasons occurring in February, July, and September. Known for its ski resorts and outdoor activities, Springfield is a hub for sports lovers. Nearby attractions, including lakes and national state parks, invite exploration and relaxation, making it a well-rounded destination for all types of travelers.
  • Grafton: Situated 9.7km away from Chester, Grafton is a picturesque city that draws visitors for its outdoor adventures and stunning scenery. With peak travel times in July and September to October, Grafton is perfect for those seeking both adrenaline-pumping activities and serene landscapes. The nearby ski fields and resorts cater to winter sports enthusiasts, while the surrounding valleys and mountains offer breathtaking views and trails for hiking and exploring in the warmer months.

Things to do near Chester

Chester, Vermont, is a perfect destination for ski enthusiasts and adventure seekers. Visitors can enjoy a variety of skiing options at local ski resorts, along with numerous outdoor activities. Beyond the slopes, the town features quirky shops that add a unique charm to your experience. Whether you're hitting the trails or exploring the local boutiques, Chester offers a delightful mix of adventure and leisure for every traveler.

Shopping

In Chester, you can shop at the Vermont Country Store and My Minds Design, both located 9.7km away. If you're up for a drive, visit the West River Farmers Market, 17.7km away, for a vibrant local market experience with fresh produce and unique crafts.

Recreation

Fox Run Golf Course offers a picturesque setting for golf enthusiasts, featuring lush greens and outdoor activities just 19.3km from Chester. For a more relaxed atmosphere, visit The Ice House Ice Skating, located 20.9km away, where you can enjoy skating in a tranquil environment. Stratton Mountain Golf Course, also 20.9km away, provides more outdoor sports opportunities amidst stunning views.

Adventure

At Okemo Mountain Resort, 17.7km from Chester, experience thrilling skiing and snowboarding on diverse trails. The Solitude Express Ski Lift, located 19.3km away, offers breathtaking views and easy access to adventure slopes. For an unforgettable experience, soar through the skies at Morningside Flight Park, also 19.3km from Chester.

Nightlife

Experience a vibrant nightlife in Chester with a visit to the Weston Playhouse for captivating performances, or enjoy family fun at Maple Lanes arcade. For a dose of culture, catch a show at the Bellows Falls Opera House, where romance and entertainment blend seamlessly.

*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, Vermont, consider visiting during the off-peak months of April to May or November, when accommodation prices are lower. Tuesdays are the cheapest days to stay, while Fridays tend to be more expensive. Use Expedia to filter for budget-friendly hotels and combine your bookings for flights and activities to secure package deals. Additionally, explore free local attractions and utilize public transport for affordable travel around the area, ensuring a memorable yet cost-effective vacation.

  • 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: Utilize Expedia's search tool to customize your preferences, such as budget, desired location, and the type of hotel you’re looking for. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservations in Chester with your flights and activities through an Expedia package deal.

Find the best attractions near Chester

Chester, Vermont, is an ideal destination for ski enthusiasts and adventure seekers, offering a variety of outdoor activities and cultural experiences. Visitors can explore beautiful parks, historical museums, and state parks that cater to families and travelers looking for enriching experiences. Whether you're in the mood for sports or simply soaking in the local history, Chester provides a unique blend of nature and culture for an unforgettable vacation.

  • Vermont Museum of Mining and Minerals: Located 9.7km from Chester, this museum offers a fascinating glimpse into Vermont's mining history. Families can explore interactive exhibits and discover the rich geological resources of the region, making it both educational and entertaining.
  • Lowell Lake State Park: Just 14.5km away, this state park is a haven for outdoor enthusiasts. With its stunning scenery, visitors can enjoy hiking, fishing, and picnicking amidst nature’s beauty, providing a perfect backdrop for adventure seekers.
  • Grafton Historical Society: Situated 9.7km from Chester, this historical society presents a deep dive into local history. Visitors can appreciate the cultural heritage of the area through exhibits and artifacts, enriching their understanding of Grafton's past.

Best time to go to Chester

The best time to visit Chester is dependent 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, there are several nearby airports to consider. Lebanon Municipal Airport (LEB) is located 46.7km away, with nearby accommodations like the 4-star Hanover Inn Dartmouth, 8.0km from the airport, and the 3-star Hotel Coolidge, 3.2km away. Rutland Southern Vermont Regional Airport (RUT) is 28.0km away, featuring hotels such as the 3.5-star Killington Mountain Lodge, 17.7km from the airport, and the Snowed Inn, also 17.7km away. The closest option is Hartness State Airport (VSF) in Springfield, just 11.3km away, with the 4-star Inn at Weathersfield located 1.6km from the airport, offering convenient access to Chester.

Frequently asked questions

Where is the best place to stay in Chester?
Based on our traveler 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 trip to the area are Woodstock Inn & Resort and Pointe at Castle Hill Resort. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental that Chester has to offer?
Mountainside 5-BR Ski-In/Out Okemo Villa: You might want to consider this vacation rental near Chester, which is located in the mountains and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a 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 provided that you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
Where can I learn more about changing or cancelling my trip to Chester?
For additional details about rescheduling or cancelling your trip to Chester, head over to our customer service page.
What's the best hotel for a family vacation to 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. Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are also fun for kids of all ages. Find more child-friendly accommodations in Chester.
What's the best accommodation for a romantic vacation in Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favorite guesthouse for couples, and features free WiFi and a garden. See all romantic hotels in Chester.
What's the best pet-friendly accommodation in Chester?
Motel in the Meadow is a top pet-friendly option for your stay. Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains is another good option for a stay with your pet. See more pet-friendly hotel accommodations in Chester.
What are some accommodations 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 with an onsite pool. View all hotels with pools in Chester.
What's the best accommodation near Hartness State Airport (VSF)?
The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.
What is staying in Chester like?
Visitors to Chester are sure to enjoy the ski areas, coffeehouses, and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 66 hotels and other accommodations to choose from. Find out more about Chester.
What should I see while I'm in Chester?
A couple of favorite 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. Check out what more 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 temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.