Find hotels in Chester, VT from $91

These Chester insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: August 14, 2026.

Top reasons to visit Chester

• Outdoor Adventure: Chester is perfect for skiing and outdoor sports, offering excellent local resorts and fields for adventure enthusiasts.
• Charming Accommodations: Enjoy a variety of cozy stays, from agritourism properties to welcoming bed & breakfasts, catering to all types of travelers.
• Scenic Parks: Explore beautiful parks and landmarks ideal for family outings and peaceful nature walks.
• Rich Local Culture: Experience the friendly atmosphere and rich history that make Chester a memorable destination.
• Golf Opportunities: Golf lovers will find numerous activities to enjoy in the picturesque surroundings of Chester.

Find great hotels near Chester

Discover charming accommodations in Chester, Vermont, where you'll find a variety of options including agritourism properties and cozy bed & breakfasts. Perfect for families, adventure seekers, and pet lovers alike, Chester's hotels offer a welcoming atmosphere and essential amenities to ensure a memorable stay. Whether you're searching for the best hotels or a quaint inn, Chester has something for every traveler.

• Pointe at Castle Hill Resort: Nestled 9 miles from Chester, this 3.5-star resort, rated 8.8, offers a vibrant adventure-themed experience perfect for thrill-seekers and business travelers alike. Guests can indulge in a variety of onsite activities, including skiing, mountain biking, and ziplining. The resort also features a luxurious full spa and pool service, providing options such as deep tissue massages and hot stone treatments, ensuring you unwind after a day of adventure.
• Best Western Springfield Hotel: Located 8 miles from Chester, this budget-friendly hotel boasts a guest rating of 8.8 and is ideal for pet owners looking for a comfortable stay. The hotel welcomes pets with specific amenities, making it a convenient choice for travelers who wish to bring their furry friends along. Its friendly atmosphere, combined with essential services, ensures a pleasant experience for all guests.
• Jackson Gore Village, A Vail Resorts Property: Situated 13 miles from Chester, this 3-star property, rated 8.6, is perfect for families and ski enthusiasts. With easy access to ski lifts and shuttles, guests can enjoy winter sports such as snowshoeing and snowboarding right at their doorstep. Families will appreciate the child-friendly amenities, including a playground and arcade game room, making it a fantastic choice for a fun-filled family getaway.

Where to stay in and around Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation for every traveler. This charming town is perfect for skiing and outdoor sports, while nearby resorts provide a touch of luxury. Experience the welcoming atmosphere of friendly locals and explore the rich history of the region. Whether you're seeking budget-friendly options or a serene getaway, Chester and its surrounding areas promise unforgettable memories for your vacation.

• Ludlow: Nestled 11 miles from Chester, Ludlow is a charming city that draws visitors year-round, especially from December to February when winter sports enthusiasts flock to its renowned ski resorts. This destination offers thrilling ski adventures along with picturesque views of nearby lakes and mountains. Outdoor lovers can also explore the stunning landscapes of national and state parks. Whether you're hitting the slopes or enjoying a cozy lodge, Ludlow provides an exhilarating getaway for adventure seekers.
• Springfield: Just 6 miles from Chester, Springfield is a vibrant city that attracts travelers throughout the year, peaking in February, July, and September. With a similar appeal to Ludlow, Springfield offers excellent skiing opportunities and access to beautiful lakes and mountains. The city boasts an array of outdoor activities, making it a fantastic spot for sports enthusiasts and adventurous spirits. Enjoy the local charm while indulging in the thrill of winter sports or summer hiking in its breathtaking natural surroundings.
• Andover: Located within the Chester area, Andover is a quaint village that welcomes visitors year-round, with peak arrivals from July to September. This serene destination is perfect for those seeking a more laid-back experience while still enjoying exciting recreational activities like skiing and exploring the surrounding lakes and mountains. Andover offers a unique charm with its natural beauty, including stunning archipelagos, making it an ideal stop for anyone looking to unwind while still embracing the spirit of adventure.

Things to do near Chester

Chester, Vermont, is an ideal destination for ski enthusiasts and adventure seekers, offering excellent skiing opportunities at local resorts and fields. The area is perfect for a weekend getaway, with various sightseeing experiences available for visitors. Golf lovers will also find activities to enjoy. Whether you're looking for interactive adventures or relaxing sightseeing journeys, Chester promises a memorable vacation filled with outdoor fun.

Shopping

In Chester, visit local shops like The Vermont Country Store for unique gifts and souvenirs. If you're up for a drive, check out the Green Mountain Shopping Plaza, located 12 miles away, which offers a mix of retail stores and dining options for a pleasant shopping experience.

Recreation

At Brattleboro Country Club, located 27 miles from Chester, you can indulge in luxury wellness activities amid picturesque landscapes. Enjoy serene golf courses, unwind with spa treatments, and savor gourmet dining options, all designed to rejuvenate your mind and body in a tranquil setting.

Adventure

Explore the scenic trails at the Green Mountain National Forest for hiking and breathtaking vistas. For a thrilling experience, try zip-lining at Okemo Mountain Resort, where you can soar through the treetops and enjoy panoramic views of the beautiful Vermont landscape.

Nightlife

Explore the cozy atmosphere at The Fullerton Inn, where you can enjoy local brews and live music. For a laid-back vibe, visit the Chester Depot for trivia nights and friendly gatherings. Don't miss the charming local pubs for a taste of Vermont's craft beers and warm hospitality.

Booking tips and Expedia advantages for Chester

• 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 tailor your options based on your budget, desired location, and preferred hotel type. To find the best prices and offers, simply arrange 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 in and around Chester

Chester, Vermont, is a fantastic destination for ski and adventure enthusiasts, offering a blend of outdoor activities and cultural experiences. Visitors can explore beautiful parks and landmarks, ideal for family outings and outdoor adventures. Whether you're hitting the slopes or enjoying the scenic beauty, Chester has something for everyone looking to create lasting memories in this charming locale.

• Bonnie's Bundles Dolls: Step into a charming world at Bonnie's Bundles Dolls, where romantic vibes intertwine with handcrafted artistry. This unique attraction in Chester showcases an array of beautifully crafted dolls, perfect for collectors and those seeking a sentimental gift.
• Lake Rescue: Experience the serene beauty of Lake Rescue, located 14 miles from Chester. This picturesque lake offers outdoor adventures, a lovely beach, and breathtaking scenery, making it an ideal spot for a romantic getaway or a family picnic.
• Lowell Lake State Park: Just 9 miles away, Lowell Lake State Park is a nature lover's paradise. With stunning scenery and plenty of outdoor activities, this state park invites you to embrace adventure while exploring its pristine landscapes.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	20.7°F (-6.3°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly High
February	22.6°F (-5.2°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly High
March	30.7°F (-0.7°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
April	42.8°F (6.0°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Average	Slightly Low
June	63.1°F (17.3°C)	Light Rain	Mostly Sunny	Average	Average
July	69.3°F (20.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	48.6°F (9.2°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	36.1°F (2.3°C)	Light Rain	Mostly Sunny	Average	Slightly Low
December	27.3°F (-2.6°C)	Light Rain	Mostly Cloudy	Average	Average

The nearest major airports for your trip to Chester

When visiting Chester, Vermont, you can consider flying into several major airports. Hartford, CT (BDL-Bradley Intl.) is 92 miles away, with nearby hotels like the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport. ALBany, NY (ALB-Albany Intl.) is 71 miles away, offering options such as The Landing Hotel at Rivers Casino & Resort, located 8 miles from the airport. Burlington, VT (BTV-Burlington Intl.) is 88 miles away, featuring the 4-star DoubleTree by Hilton Burlington Vermont, only 2 miles from the airport. Each airport provides accessible transportation options to nearby hotels for a convenient travel experience.