Find hotels in Chester, VT from CA $128

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Compare 2,923 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (780)
"Great stay!"
The price is CA $161
CA $177 total
includes taxes & fees
Sep 3 - Sep 4
Latchis Hotel

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1009)
"Great for stay"
The price is CA $219
CA $237 total
includes taxes & fees
Sep 3 - Sep 4
Best Western Plus Keene Hotel

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (317)
"We stayed one night. We were able to get checked early, enjoyed breakfast, quiet and charming atmosphere. Owners are very friendly. "
The price is CA $189
CA $208 total
includes taxes & fees
Sep 3 - Sep 4
Colonel Williams Inn

Fullerton Inn

2.5 star property
8.2 out of 10, Very good, (371)
"Everything was Awsome friendly staff"
The price is CA $191
CA $208 total
includes taxes & fees
Sep 3 - Sep 4
Fullerton Inn

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (94)
"Sweet place to stay"
The price is CA $300
CA $327 total
includes taxes & fees
Sep 3 - Sep 4
Stone Hearth Inn and Eatery

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1008)
"Very enjoyable stay"
The price is CA $147
CA $162 total
includes taxes & fees
Sep 3 - Sep 4
The Putney Inn

Claremont Motor Lodge

2.5 star property
8.6 out of 10, Excellent, (383)
"Great place to stay"
The price is CA $154
CA $167 total
includes taxes & fees
Sep 3 - Sep 4
Claremont Motor Lodge

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
8.4 out of 10, Very good, (890)
"Had a great time at this location"
The price is CA $172
CA $187 total
includes taxes & fees
Sep 9 - Sep 10
Keene Elm City Hotel, an Ascend Collection Hotel

The Manchester View

2.5 star property
9.4 out of 10, Exceptional, (746)
"We enjoyed our stay. Clean, great staff, great continental breakfast!"
The price is CA $180
CA $199 total
includes taxes & fees
Sep 7 - Sep 8
The Manchester View

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (378)
"Small rustic motel with lounge near Bromley winhall etc best prices around and clean overall. Nice staff decent breakfast "
The price is CA $183
CA $201 total
includes taxes & fees
Sep 3 - Sep 4
Bromley View Inn

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (330)
"Great hotel with friendly staff"
The price is CA $255
CA $276 total
includes taxes & fees
Sep 9 - Sep 10
Hampton Inn & Suites Keene

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (225)
"Enjoyed our stay - learning more about Inns and how they are not Hotels. Very pleasant - we'd stay there again."
The price is CA $175
CA $191 total
includes taxes & fees
Sep 7 - Sep 8
Harvest Barn Inn

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (516)
"Rooms are very clean , staff are very friendly , we enjoy our stay here . "
The price is CA $142
CA $179 total
includes taxes & fees
Sep 8 - Sep 9
Sleep Woodstock Motel

Brittany Motel

2.0 star property
9.4 out of 10, Exceptional, (318)
"We stayed in the cactus room and we loved the green bathroom. There is a lounge (a HUGE hit with my kiddo too) and the staff was great. WiFi was good (I worked from the room). We would stay there again."
The price is CA $158
CA $197 total
includes taxes & fees
Sep 3 - Sep 4
Brittany Motel

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (154)
"Excellent phenomenal cleanliness and so polite"
The price is CA $244
CA $264 total
includes taxes & fees
Sep 3 - Sep 4
The Carriage Barn Inn

Lincoln Inn & Gallery

3.0 star property
9.4 out of 10, Exceptional, (35)
"This place was great I cannot say enough about the innkeepers and the staff all in all you'll love it!!"
The price is CA $198
CA $218 total
includes taxes & fees
Sep 3 - Sep 4
Lincoln Inn & Gallery

Aerie Inn of Vermont

2.0 star property
9.4 out of 10, Exceptional, (163)
"So quaint and staff was super friendly and accommodating! We are looking forward to coming back again! "
The price is CA $163
CA $178 total
includes taxes & fees
Sep 3 - Sep 4
Aerie Inn of Vermont

Four Winds Country Motel

2.0 star property
8.4 out of 10, Very good, (508)
"Quiet, clean and nice staff. Nicely decorated. Love the pool!"
The price is CA $207
CA $228 total
includes taxes & fees
Sep 3 - Sep 4
Four Winds Country Motel

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1008)
"Would stay again"
The price is CA $158
CA $171 total
includes taxes & fees
Sep 7 - Sep 8
Days Inn by Wyndham Keene NH

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (461)
"Friendly staff. Room was nice "
The price is CA $182
CA $200 total
includes taxes & fees
Sep 3 - Sep 4
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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Check out pet-friendly hotels in Chester

Hotels with a hot tub in Chester may fit your trip

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.

Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most.

Chester Depot

2 out of top 10 points of interest in this area

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

DaVallia Art & Accents

DaVallia Art & Accents

Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.

Bonnie's Bundles Dolls

Bonnie's Bundles Dolls

Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views, or seek out its ski slopes.

More cheap stays in Chester

More cheap stays in Chester

Hotels in Chester with star-rating

Hotels in Chester with star-rating

Find out more about Chester

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester is perfect for skiing, hiking, and exploring local parks, catering to all adventure enthusiasts.
  • Rich History: History buffs can explore the area’s heritage at the local history museum, offering insights into the past.
  • Charming Accommodations: Enjoy a variety of cozy bed & breakfasts and agritourism properties for a unique stay.
  • Scenic Beauty: The picturesque surroundings provide stunning views and a tranquil atmosphere away from crowds.
  • Family-Friendly Activities: Chester offers various activities for families, ensuring a well-rounded vacation experience.

Find great hotels near Chester

Discover a charming selection of accommodations in Chester, Vermont, where agritourism properties and cozy bed & breakfasts cater to every type of traveler. Whether you're seeking family-friendly options, adventurous getaways, or pet-friendly stays, Chester offers a variety of hotels and inns to ensure a memorable experience. Explore the best hotels in the area, including the inviting Chester Inn, to enjoy a delightful stay in this picturesque New England town.

  • Best Western Springfield Hotel: Embrace a pet-friendly getaway at the Best Western Springfield Hotel, located 12.9km from Chester. This welcoming property is perfect for travellers looking to bring their furry friends along for the adventure. With amenities tailored for pets, including designated areas for dogs and a relaxed atmosphere, guests can enjoy a comfortable stay while exploring the surrounding beauty of Vermont. Convenience meets hospitality in this family-friendly hotel, making it an excellent choice for those seeking a home away from home.
  • Pointe at Castle Hill Resort: Experience the perfect blend of business and leisure at Pointe at Castle Hill Resort, just 14.5km from Chester. This 3.5-star hotel caters to business travellers with accessible meeting rooms and a fully equipped business centre. For those craving adventure, the resort offers a variety of outdoor activities, including fishing, skiing, and ziplining. After an exhilarating day, unwind at the full-service spa featuring massages and body treatments. Whether you're here for business or pleasure, this resort ensures an enriching stay.
  • Jackson Gore Village: Ideal for families and golf enthusiasts, Jackson Gore Village is located 20.9km from Chester and offers a delightful blend of relaxation and recreation. With amenities designed for children, including a playground and arcade games, families can enjoy quality time together. Golfers will appreciate the on-site golfing experience, while the full-service spa provides rejuvenating treatments like hot stone and deep tissue massages. This 3-star hotel combines family fun with wellness, making it an excellent choice for a memorable vacation.

Where to stay near Chester

Chester, Vermont, offers a delightful blend of historic charm and outdoor adventure, making it an ideal weekend getaway for Canadian travellers. Nestled in southern Vermont, this quaint town is perfect for skiing and sports, while also providing a relaxing atmosphere with low crowds. Explore nearby cities for a taste of luxury or budget-friendly options, all set against a backdrop of friendly locals and stunning scenery. Chester promises an unforgettable experience for every type of visitor.

  • Ludlow: Nestled 17.7km from Chester, Ludlow is a charming city that comes alive during the winter months, attracting visitors for its thrilling ski adventures. With its picturesque mountains and expansive ski resorts, it's a perfect destination for snow sports enthusiasts. Beyond skiing, Ludlow offers stunning views of lakes and valleys, making it an ideal spot for outdoor exploration year-round. Whether you’re hitting the slopes or taking a scenic hike, Ludlow promises a memorable travel experience.
  • Springfield: Just 9.7km away from Chester, Springfield is a vibrant city known for its year-round appeal. It attracts visitors for skiing, outdoor adventures, and sports, with peaks in travel during February, July, and September. The nearby national state park offers breathtaking landscapes, lush lakes, and mountain trails for hiking and exploration. Springfield’s blend of natural beauty and recreational activities ensures a delightful experience for every type of traveller.
  • Grafton: Located a mere 9.7km from Chester, Grafton is a quaint city that captivates outdoor enthusiasts seeking ski adventures and tranquil landscapes. While it sees its highest visitor numbers during the summer and early autumn, Grafton offers a year-round charm with its stunning lakes, valleys, and mountains. The area is perfect for skiing in the winter and hiking or biking in the warmer months, providing a fantastic escape into nature while still enjoying local culture.

Things to do near Chester

Chester, Vermont, offers an exciting blend of skiing and outdoor adventures, making it an ideal destination for sports enthusiasts. Visitors can enjoy various activities at local ski resorts, explore scenic sightseeing opportunities, and unwind around cozy fire pits. Whether you're hitting the slopes or relaxing in the great outdoors, Chester promises a memorable vacation experience for all.

Shopping

In Chester, visit the Vermont Country Store, a charming spot located 9.7km away, offering unique gifts and Vermont-made products. My Minds Design, also 9.7km away, features eclectic home décor. If you're up for a drive, the West River Farmers Market, 17.7km away, showcases local produce and crafts.

Recreation

Experience the scenic Fox Run Golf Course, just 19.3km from Chester, where you can enjoy outdoor sports in a vibrant atmosphere. Alternatively, indulge in wellness and relaxation at The Ice House Ice Skating, located 20.9km away, perfect for unwinding with friends and family.

Adventure

At Okemo Mountain Resort, located 17.7km from Chester, experience thrilling skiing amidst stunning landscapes. Morningside Flight Park, 19.3km away, offers breathtaking scenic flights that will elevate your adventure. For more excitement, try the Solitude Express Ski Lift, also 19.3km from Chester, providing exhilarating access to the slopes.

Nightlife

In Chester, Vermont, the nightlife offers a mix of culture and entertainment. The Weston Playhouse and Bellows Falls Opera House provide captivating theatrical experiences, while Maple Lanes ArcadeAdventureZone adds an adventurous twist with fun arcade games, perfect for families and friends seeking a lively night out.

*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 and November for lower accommodation prices. Tuesdays are the most affordable days to stay, while Fridays tend to be pricier. Use Expedia’s search tool to find budget-friendly options, and consider eco-certified hotels for sustainable choices. Additionally, combining your hotel, flights, and activities into an Expedia package can lead to significant savings. Take advantage of free activities in the area, and explore on foot to save on transportation costs.

  • 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 refine your preferences based on your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. 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 stay in Chester with your flights and activities by choosing an Expedia package.

Find the best attractions in and around Chester

Chester, Vermont, is an excellent destination for adventure seekers and sports enthusiasts alike. Visitors can enjoy various activities in local parks and state parks, while history buffs can explore the area's rich heritage at the history museum. With its emphasis on outdoor experiences, cultural attractions, and family-friendly activities, Chester offers a well-rounded vacation for all types of travellers looking to immerse themselves in nature and local history.

  • DaVallia Art & Accents: Immerse yourself in the vibrant culture of Chester at this unique gallery. Featuring local artists and captivating exhibitions, DaVallia Art & Accents offers a delightful experience for art enthusiasts and casual visitors alike.
  • Lowell Lake State Park: Just 14.5km from Chester, this stunning park is perfect for outdoor adventurers. With its picturesque scenery, hiking trails, and serene lake, you can enjoy activities like kayaking, fishing, or simply soaking in nature's beauty.
  • Bonnie's Bundles Dolls: Located in Chester, this charming attraction is a delightful stop for families and collectors. With its romantic atmosphere and handmade dolls, Bonnie's Bundles Dolls offers a nostalgic experience that warms the heart.

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

To visit Chester, Vermont, you have several airport options. Lebanon Municipal Airport (LEB) is situated 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 from LEB. Rutland Southern Vermont Regional Airport (RUT) is 28.0km away, with options such as the 3.5-star Killington Grand Hotel, 16.1km from RUT. Lastly, Hartness State Airport (VSF) is conveniently located just 11.3km from Chester, with nearby stays like the 4-star Inn at Weathersfield, 1.6km away. Each airport offers various transportation services to ensure a smooth arrival.

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Explore a world of travel with Expedia

Frequently asked questions

What is the best area to stay in Chester?
Chester Depot is the premier area to stay for travellers seeking both adventure and tranquillity in Vermont. This charming village combines picturesque landscapes with a welcoming community feel. Nestled between lush mountains and serene rivers, Chester Depot offers easy access to outdoor activities such as hiking and skiing in the nearby Green Mountains. The quaint downtown area features delightful shops, local eateries, and a rich history that beckons exploration.

For couples planning a romantic escape, Chester Depot provides an idyllic backdrop. Stroll hand-in-hand along the scenic paths or enjoy a cosy meal at one of the charming bistros. The peaceful surroundings and stunning views create the great setting for memorable moments together.

Families will also find Chester Depot appealing, as it offers a wealth of outdoor adventures suitable for all ages. From exploring the nearby state parks to enjoying family-friendly festivals, there's something for everyone. The community's warm hospitality ensures that families feel right at home while making lasting memories.
What are the best hotels in Chester that travellers recommend?
Stone Hearth Inn and Eatery is a highly praised option in Chester, boasting an exceptional score of 9.2. This charming inn offers breathtaking mountain views and air-conditioned comfort, making it a relaxing retreat for couples seeking a romantic getaway or simply a peaceful escape from daily life. Guests rave about the cozy atmosphere and attentive service, ensuring a memorable stay.
What are the best family hotels in Chester?
Stone Hearth Inn and Eatery in Chester, Vermont, is a delightful family-friendly retreat, boasting a traveller review score of 9.2, which reflects its warm hospitality and friendly setting. This charming inn offers a range of amenities designed to cater to families, including complimentary cribs and rollaway beds, ensuring that everyone has a comfortable stay. Find more child-friendly accommodations in Chester.
What hotels in Chester offer free breakfast?
Stone Hearth Inn and Eatery is a charming option in Chester, Vermont, known for its friendly space and excellent service, achieving an excellent review score of 9.2 from guests. This delightful inn offers a complimentary breakfast that features a buffet, allowing guests to start their day on a delicious note while enjoying breathtaking mountain views right from the property. Find more hotels with free breakfast in Chester.
What are the best budget hotels in Chester?
Stone Hearth Inn and Eatery is a charming option for budget-conscious travellers seeking both comfort and convenience. With an impressive review score of 9.2, guests rave about the complimentary buffet breakfast and free in-room WiFi, making it easy to start your day and stay connected. Nestled in a picturesque mountain location, this inn offers easy access to outdoor adventures such as skiing, mountain biking, and cross-country skiing, ensuring that families and adventure-seekers alike will find their thrills nearby.

For families, the Stone Hearth Inn is particularly accommodating, providing free cribs and highchairs, along with an assortment of books and games for children. This thoughtful attention to family needs creates a inviting space for those traveling with kids.

Another budget-friendly property in Chester is the Motel in the Meadow, which has a review score of 8.4. This cozy motel allows pets, making it an excellent choice for families who want to travel with their furry companions. Guests appreciate the included continental breakfast and the convenience of free self-parking. View all budget hotels in Chester.
When is the best time to go to Chester?
The best time to visit Chester is during the late spring and early autumn months, particularly in May and September. In May, temperatures typically range from 10 to 17°C, creating a refreshing atmosphere great for exploring the city's historic sites and beautiful gardens. September, with similar mild conditions, offers the added charm of a vibrant community calendar filled with events and festivals.

The peak tourist season runs from July to August when Chester sees the highest influx of visitors. During these months, you can enjoy a lively atmosphere, with numerous outdoor activities and cultural events taking place. The pleasant weather encourages leisurely strolls along the River Dee or through the picturesque rows of half-timbered buildings in the city centre.

If you're someone who enjoys a good balance between pleasant weather and fewer crowds, May is particularly appealing. The blooming flowers in the city's parks and gardens create an enchanting backdrop for your adventures, while the overall atmosphere remains relaxed and welcoming. Plus, with lower accommodation prices compared to the peak summer months, you'll find excellent value for your stay.

September is another wonderful option, especially for couples or those interested in cultural experiences. The city often hosts events celebrating local heritage, giving you a chance to engage with the community and discover Chester's rich history. Outdoor dining becomes a delightful experience as many restaurants offer al fresco seating, allowing you to enjoy local delicacies while soaking in the charming surroundings.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Chester hotel for you.
How can I save on a Chester hotel booking with Expedia?
With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Chester hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.
How much is the nightly rate at a Chester hotel?
Prices for hotels in Chester often vary, but you can find a great deal from CA $128 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.