Find hotels in Cheshire, MA from $88

Top reasons to visit Cheshire

• Outdoor Adventures: Cheshire is a haven for outdoor enthusiasts, offering skiing and scenic trails for all skill levels.
• Charming Towns: Explore nearby towns with friendly attractions, showcasing the region’s historic charm.
• Family-Friendly Activities: The area features a variety of attractions suitable for families, ensuring fun for all ages.
• Arts and Culture: Enjoy local cultural experiences, including an arts center and a community library.
• Comfortable Lodging: Cheshire provides diverse accommodation options, from luxury stays to cozy inns.

Find great hotels near Cheshire

Cheshire, Massachusetts, offers a variety of lodging options to cater to all types of travelers. Whether you're seeking a family-friendly resort, a romantic getaway, or an adventurous vacation experience, you'll find numerous hotels that fit your needs. From luxury accommodations to highly-rated hotels with glowing reviews, Cheshire combines comfort with the charm of New England. Start exploring your perfect stay in this picturesque town today.

• Holiday Inn & Suites Pittsfield-Berkshires by IHG: Located 9 miles from Cheshire, the Holiday Inn & Suites Pittsfield-Berkshires by IHG is ideal for business travelers and families alike. This 3-star hotel offers a range of amenities designed to cater to both work and play. Business facilities include a 24-hour business center, accessible meeting rooms, and a conference center, making it a perfect choice for corporate events. Families will appreciate the child-friendly features, such as free cribs and window guards for added safety. The hotel is situated in the heart of the city, providing easy access to local attractions and dining options.
• Club Wyndham Bentley Brook: Just 6 miles from Cheshire, Club Wyndham Bentley Brook is a fantastic destination for adventure enthusiasts. This 3-star hotel is perfect for those who enjoy winter sports, with nearby ski lifts and shuttles. On-site, guests can engage in a variety of outdoor activities, including downhill skiing, snowboarding, hiking, and biking. With comfortable accommodations and a focus on adventure, this hotel is designed for thrill-seekers looking to embrace the great outdoors.
• Hotel Downstreet, Ascend Hotel Collection: Situated 10 miles from Cheshire, Hotel Downstreet offers a welcoming atmosphere tailored for LGBTQIA travelers and pet owners. This 3-star hotel embraces inclusivity, providing a safe space for all guests. The hotel is pet-friendly, allowing dogs and cats on-site, with specific amenities to ensure a comfortable stay for both pets and their owners. With its commitment to diversity and welcoming spirit, Hotel Downstreet is an excellent choice for those seeking a unique and accommodating experience.

Where to stay near Cheshire

Cheshire, Massachusetts, is the perfect destination for outdoor enthusiasts and families alike. Enjoy a weekend getaway filled with skiing, scenic adventures, and romantic moments. Explore nearby charming towns that offer friendly attractions and a glimpse into the region’s historic charm. Whether you're looking for a relaxing retreat or an action-packed vacation, Cheshire provides a diverse atmosphere that caters to every traveler's needs while showcasing the beauty of the Berkshires.

• Williamstown: Located 11 miles from Cheshire, Williamstown is a charming town known for its beautiful landscapes and vibrant arts scene. Visitors flock here primarily for skiing and outdoor adventures during the winter months, with peak travel occurring in April and from June to July. The town is home to renowned institutions like Williams College, which adds a historic and academic flair to the area. Outdoor enthusiasts can explore nearby mountains and lakes, making it an ideal spot for both relaxation and recreation.
• Pittsfield: Just 9 miles from Cheshire, Pittsfield is a lively city that offers a mix of cultural attractions and outdoor activities. The peak tourist season runs from June to August, attracting visitors eager to enjoy the local lakes and the nearby ski fields. Pittsfield is known for its waterpark, which is a great family-friendly destination during the summer months. The city’s picturesque surroundings, including mountains and recreational areas, provide ample opportunities for adventure seekers and sports enthusiasts alike.
• North Adams: Approximately 10 miles from Cheshire, North Adams is a hidden gem that is perfect for those seeking an outdoor and cultural experience. The city sees an influx of visitors during the summer, particularly in June, July, and September, who come for its adventurous offerings and ski resorts. North Adams is also home to the Massachusetts Museum of Contemporary Art (MASS MoCA) and various public art installations, making it a vibrant cultural hub. With its scenic landscapes and artistic vibe, North Adams is a must-visit on your vacation.

Things to do near Cheshire

Cheshire, Massachusetts, is an ideal destination for outdoor enthusiasts, offering a range of activities such as skiing at local resorts and exploring scenic trails. Visitors can enjoy thrilling adventures in the beautiful surroundings, as well as attractions like nearby Chester and various theme parks. Whether you're hitting the slopes or seeking outdoor fun, Cheshire provides a perfect backdrop for an unforgettable vacation.

Shopping

In Cheshire, you can enjoy local shops for gifts and souvenirs. If you're up for a drive, visit North Adams Center, North Adams Gateway Center, and Colonial Plaza, all about 10 miles away, featuring a mix of family-friendly and city vibes for your shopping pleasure.

Recreation

Skyline Country Club offers a scenic golf experience with lush fairways and stunning views, perfect for outdoor enthusiasts. For relaxation, visit Windsor Lake Park, where you can unwind by the water and enjoy nature. Waubeeka Golf Links provides another excellent golfing option in a tranquil setting.

Adventure

At Jiminy Peak Mountain Resort, 7 miles from Cheshire, enjoy thrilling skiing and snowboarding on diverse slopes. Berkshire East Ski Resort, 15 miles away, offers outdoor adventures like zip-lining and mountain biking. For a scenic hike, explore the Skyline Trail, also 15 miles away, featuring stunning views and lush landscapes.

Nightlife

Experience the vibrant nightlife in Cheshire by catching a show at the Williamstown Theatre Festival, just 8 miles away, or enjoy a performance at the Adams Theater, only 5 miles from town. For family fun, the Alpine Super Slide, 7 miles away, offers an exciting amusement ride experience.

Booking tips and Expedia advantages for Cheshire

To save money on your trip to Cheshire, consider visiting during the cheaper months of March to April or November, and aim for a Tuesday stay, as Saturday rates are the highest. Use Expedia to compare room rates, customize your search, and book package deals that combine hotels, flights, and activities for greater savings. Joining the Expedia One Key membership can provide exclusive discounts and OneKeyCash for future bookings. Additionally, explore free local activities and utilize public transport to keep your expenses low.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Cheshire are March to April and November, 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 Cheshire is Tuesday. The most expensive day to stay in Cheshire is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia's search tool to customize your preferences, such as your budget, desired location, and preferred hotel type. To find the best prices and deals, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Cheshire with your flights and activities through an Expedia package.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Cheshire

Cheshire, Massachusetts, is perfect for travelers seeking outdoor adventures and cultural experiences. The area offers a variety of attractions, including scenic mountains, a local library, and an arts center. Whether you're into skiing, exploring nature, or enjoying family-friendly activities, Cheshire has something for everyone. Plan your visit to discover the charm and excitement this quaint town has to offer.

• Mount Greylock: Experience breathtaking views from the highest point in Massachusetts, just 5 miles from Cheshire. Hike through scenic trails and immerse yourself in the natural beauty of the outdoors, perfect for adventure seekers and nature lovers alike.
• Mount Greylock State Reservation Visitor Center: Located 3 miles away, this visitor center offers a gateway to adventure with family-friendly activities and educational exhibits. Explore the surrounding lush landscapes and learn about the rich history of the region.
• Williams College: A short 10-mile drive will take you to this prestigious institution, where you can stroll through its historic campus, admire beautiful architecture, and soak in the vibrant cultural atmosphere of the college community.

Best time to go to Cheshire

The best time to visit Cheshire can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Cheshire falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Cheshire falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	19.9°F (-6.7°C)	Light Rain	Mostly Cloudy	Average	Average
February	22.1°F (-5.5°C)	Light Rain	Mostly Cloudy	Moderately Low	Average
March	29.7°F (-1.3°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	41.4°F (5.2°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	53.8°F (12.1°C)	Light Rain	Mostly Sunny	Average	Average
June	61.5°F (16.4°C)	Light Rain	Mostly Sunny	Moderately High	Average
July	67.6°F (19.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	65.7°F (18.7°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
September	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Average	Average
October	47.7°F (8.7°C)	Light Rain	Mostly Cloudy	Average	Slightly High
November	35.4°F (1.9°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
December	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Moderately Low	Average

The nearest major airports for your trip to Cheshire

To visit Cheshire, Massachusetts, you can fly into three major airports. Hartford, CT (BDL-Bradley Intl.) is approximately 50 miles away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, located 1 mile from the airport. Albany, NY (ALB-Albany Intl.) is about 35 miles away, offering options such as the Park Manor Hotel, just 8 miles from the airport. The closest option is Pittsfield, MA (PSF-Pittsfield Municipal), located 12 miles from Cheshire, with accommodations like The Central Downtown Inn & Suites, 2 miles away. Each airport is easily accessible from these hotels, providing convenient transportation for your trip.