Find hotels in Chester, MA from $68

These Chester insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: August 26, 2026.

Top reasons to visit Chester

• Outdoor Adventures: Chester is an ideal destination for hiking, skiing, and enjoying various outdoor activities amidst its scenic landscapes.
• Charming Accommodations: The town offers a range of cozy stays, from bed and breakfasts to comfortable hotels, catering to all types of travelers.
• Historic Sites: Explore local history through picturesque historic houses and charming urban parks.
• Family-Friendly Atmosphere: The town welcomes families with activities that provide fun for all ages.
• Romantic Getaways: Chester's serene environment makes it perfect for couples seeking a romantic escape.

Find great hotels near Chester

Explore the charming town of Chester, Massachusetts, and discover a variety of hotel accommodations tailored to your needs. From cozy bed and breakfasts to comfortable hotels, you'll find options perfect for family vacations or adventurous getaways. Whether you're looking for pet-friendly options or the best hotels to enjoy a memorable stay, Chester offers a welcoming atmosphere for all travelers.

• Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This 3.5-star resort, with an impressive guest rating of 9.0, is a fantastic choice for those seeking a family-friendly adventure in the Berkshires. Located 15 miles from Chester, the resort offers easy access to ski lifts and shuttles, making it ideal for winter sports enthusiasts. Families will appreciate the on-site playground, arcade game room, and mini-golf, while adventure seekers can enjoy a variety of activities like skiing, snowboarding, and hiking. With its emphasis on recreation and comfort, this resort ensures a memorable stay for guests of all ages.
• The Black Swan Lee - Lenox, an Ascend Collection Hotel: Rated 9.2 and conveniently located 15 miles from Chester, this 3-star hotel is perfect for families and pet lovers alike. The Black Swan Lee - Lenox offers a cozy atmosphere with amenities for children, including cribs and safety features. Guests can partake in various activities such as fishing, skiing, and snow tubing. The hotel’s pet-friendly policy allows for a stress-free stay with your furry friends. Whether you're looking for a relaxing getaway or an exciting outdoor adventure, this hotel's unique charm and welcoming environment will make your visit unforgettable.
• Quality Inn Westfield - Springfield: A budget-friendly option, the Quality Inn Westfield - Springfield is located 16 miles from Chester and offers a comfortable stay for families and business travelers. With a guest rating of 8.0, this hotel provides essential amenities such as free cribs for children and a pet-friendly policy, allowing you to bring your four-legged companions along. The hotel's convenient location offers easy access to local attractions, making it a practical choice for those seeking value and comfort on their trip.

Where to stay near Chester

Chester, Massachusetts, is a charming city perfect for outdoor adventures and romantic getaways. Explore its scenic views and historic sites while enjoying a family-friendly atmosphere. Nearby regions offer a relaxing vibe, ideal for recreation and leisurely strolls. Whether you're hiking through picturesque landscapes or indulging in local culture, Chester and its surroundings promise memories filled with charm and beauty awaiting your discovery.

• Lenox: Nestled 17 miles from Chester, Lenox is a charming city that attracts visitors year-round, with peak travel in the summer months. Known for its rich cultural scene, Lenox offers a delightful mix of entertainment, romance, and artistic experiences. Enjoy music concerts and theatrical performances at renowned venues, or hit the nearby ski slopes in winter. The scenic beauty of the area is enhanced by picturesque lakes and mountains, making it a perfect spot for outdoor enthusiasts. Don't miss the local event conference venues that often host exciting gatherings and celebrations.
• The Berkshires: Just 12 miles from Chester, The Berkshires is a diverse region that invites adventure seekers and nature lovers alike. With a steady flow of visitors throughout the year, the area is particularly lively from June to August. Here, you can immerse yourself in outdoor activities, from skiing at top-notch resorts to exploring the stunning scenery of the mountains and lakes. The Berkshires is also home to various events and conferences, adding to its appeal as a vibrant destination for tourists seeking both excitement and relaxation.
• Lee: Located 14 miles from Chester, Lee is a delightful city that welcomes travelers with its family-friendly atmosphere and romantic charm. With a consistent influx of visitors year-round, peak seasons occur in the summer. Lee boasts a variety of entertainment options, including theaters and live music concerts, ensuring a lively experience. The area's natural beauty is complemented by historical monuments and serene lakes, providing the perfect backdrop for leisurely strolls and family outings. Whether you're seeking a cozy getaway or an action-packed adventure, Lee has something for everyone.

Things to do in Chester

Chester, Massachusetts, is perfect for outdoor adventures and romantic getaways. Visitors can enjoy skiing at local ski fields, catch a performance at the theater, or hit the golf course for a round of golf. With its scenic landscapes and charming attractions, Chester invites exploration through its various amenities and local sights, making it an ideal destination for those seeking both relaxation and adventure.

Shopping

In Chester, you can explore local shops offering unique crafts and souvenirs. If you're up for a drive, head to the nearby shopping malls like the Berkshire Mall in Lanesborough for a wider selection, or check out the Eastfield Mall in Springfield for more mainstream retailers.

Recreation

Chester's Wellness Retreat offers rejuvenating spa treatments, yoga sessions, and guided meditation in a tranquil setting. For outdoor enthusiasts, the surrounding scenic trails provide opportunities for hiking, birdwatching, and peaceful picnics, allowing you to recharge while immersing yourself in nature's beauty.

Adventure

In Chester, explore the scenic hiking trails of the Chester-Blandford State Forest, where you'll encounter breathtaking views and diverse wildlife. For water enthusiasts, the nearby Westfield River offers thrilling kayaking and canoeing experiences amidst beautiful surroundings, perfect for an adventurous day out.

Nightlife

Chester offers a charming nightlife experience with cozy bars and local eateries. Enjoy a drink at the Chester Tavern, where friendly locals gather. For a laid-back evening, try the nearby picnic spots along the river, perfect for stargazing and unwinding after a day of exploration.

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 March and December to January, where the prices are slightly lower. This is in comparison to July to August 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 Saturday.
• Find cheap hotels on Expedia: Utilize Expedia's search tool to narrow down your preferences, such as your budget, desired location, and 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 stay in Chester with your flights and activities through an Expedia package deal.

Find the best attractions near Chester

Chester, Massachusetts, is an ideal destination for outdoor enthusiasts, adventure seekers, and couples looking for a romantic getaway. Visitors can explore a variety of attractions, including urban parks, nature reserves, and historic houses. Whether you're seeking family-friendly activities or thrilling outdoor experiences, Chester offers a delightful mix of points of interest that cater to diverse tastes and interests.

• National Shrine of the Divine Mercy: Located 17 miles from Chester, this serene shrine offers a peaceful retreat with stunning architecture and beautiful gardens, perfect for reflection and spiritual growth.
• Becket Land Trust Historic Quarry: Just 3 miles away, this preserve combines adventure and family-friendly activities, featuring hiking trails and scenic views, making it a trendy spot for both luxury and budget travelers.
• Littleville Lake: Located 5 miles from Chester, this picturesque lake is ideal for outdoor enthusiasts, offering opportunities for swimming, picnicking, and enjoying romantic sunset views along its scenic shoreline.

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 average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	23.5°F (-4.7°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	25.3°F (-3.7°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
March	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	44.8°F (7.1°C)	Light Rain	Mostly Cloudy	Average	Average
May	56.5°F (13.6°C)	Light Rain	Mostly Sunny	Average	Average
June	64.4°F (18.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	70.5°F (21.4°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	68.7°F (20.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	61.9°F (16.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	50.7°F (10.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	30.2°F (-1.0°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low

The nearest major airports for your trip to Chester

When traveling to Chester, Massachusetts, you have several airport options. Hartford, CT (BDL-Bradley Intl.) is located 28 miles away, with nearby hotels like DoubleTree by Hilton Hartford - Bradley Airport and Marriott Hartford Downtown, both offering convenient access to the airport. Providence, RI (PVD-T.F. Green) is 88 miles from Chester, with excellent hotel choices such as Omni Providence Hotel and Hotel Providence situated 7 miles from the airport. ALBany, NY (ALB-Albany Intl.) is 53 miles away, featuring hotels like The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both 8 miles from the airport. Each location provides accessible transportation options for travelers.