Find hotels in Cheshire, MA from AED 209

Top reasons to visit Cheshire

• Outdoor Adventures: Cheshire offers thrilling activities like skiing in the Berkshire Mountains and hiking through scenic trails, perfect for adventure seekers.
• Family-Friendly Attractions: Enjoy a variety of attractions that cater to families, ensuring fun for all ages.
• Charming Town Center: Explore the quaint town center, featuring romantic spots and local shops.
• Natural Beauty: Experience the serene landscapes and nature reserves, ideal for relaxation and connecting with nature.
• Diverse Accommodations: Choose from a range of lodging options, from cozy hotels to family-friendly resorts, ensuring a comfortable stay.

Find great hotels near Cheshire

Cheshire, Massachusetts offers a diverse selection of accommodations to cater to every traveler’s needs, from family-friendly resorts to cozy hotels. Whether you're seeking a romantic getaway, an adventurous vacation, or simply a relaxing escape, you'll find a range of options that promise comfort and quality. Explore the best hotels in the area, read reviews, and discover luxury stays that elevate your experience in this charming town.

• Holiday Inn & Suites Pittsfield-Berkshires by IHG: Located a mere 14.5km from Cheshire, the Holiday Inn & Suites Pittsfield-Berkshires offers a vibrant city-themed experience perfect for families and pet lovers. This 3-star hotel boasts a welcoming atmosphere with amenities tailored for children, including free cribs and window guards for safety. Pets are also welcome, subject to specific policies, making it an ideal choice for travelers bringing furry companions. Its central location in the city provides easy access to local attractions, ensuring a memorable stay for everyone.
• Hotel Downstreet, an Ascend Collection Hotel: Just 16.1km from Cheshire, Hotel Downstreet presents a unique and inclusive environment, making it a favorite among LGBTQIA travelers. This 3-star hotel is pet-friendly, allowing both dogs and cats, and proudly supports LGBTQI travel initiatives. Guests can enjoy a comfortable stay with amenities that cater to both people and their pets. The warm and inviting ambiance of the hotel ensures that everyone feels welcome, creating a delightful retreat in the heart of the community.
• Club Wyndham Bentley Brook: Nestled only 9.7km from Cheshire, Club Wyndham Bentley Brook is the ultimate destination for adventure seekers and ski enthusiasts. This 3-star hotel offers direct access to ski lifts and shuttles, putting you right in the heart of outdoor activities. Guests can enjoy a range of adventure sports, including hiking, biking, snowboarding, and cross-country skiing—all within close proximity. With comfortable accommodations and a focus on recreation, this hotel is perfect for those looking to embrace the thrill of the Berkshires.

Where to stay near Cheshire

Cheshire, Massachusetts, offers a delightful blend of adventure and relaxation for travelers. Explore the beautiful landscapes of the Berkshire Mountains, perfect for skiing and outdoor activities. Enjoy family-friendly attractions and romantic spots in the charming town center. Nearby, discover the historic beauty of the region, making it an ideal weekend getaway. Whether you're seeking friendly vibes or scenic views, Cheshire promises a memorable vacation experience.

• Pittsfield: A vibrant city located 14.5km from Cheshire, Pittsfield is a hub for outdoor enthusiasts seeking adventure. Known for its ski resorts and beautiful landscapes, the city attracts visitors year-round, with peak travel during the summer months. Here, you can enjoy skiing during the winter, explore lakes and mountains, and visit local monuments. Pittsfield offers a blend of thrilling activities and serene natural beauty, making it an ideal destination for those looking to immerse themselves in outdoor experiences.
• Williamstown: Situated 17.7km from Cheshire, Williamstown is a charming city that draws travelers for its rich history and outdoor sports. With a peak in visitors from April to July, this city is particularly known for its ski fields and the prestigious Williams College. Explore the scenic lakes and mountains surrounding the city, or take a stroll through the historic university campus. Williamstown is perfect for adventure seekers and sports lovers alike, offering a unique blend of culture and nature.
• North Adams: Located 16.1km away from Cheshire, North Adams is a city that thrives on cultural experiences and adventure. With a peak in travelers during the summer, this vibrant city offers ski options and hosts exciting music concerts. The presence of art museums and public art installations enriches the cultural landscape, making it a great spot for art enthusiasts. North Adams invites you to explore its unique blend of adventure and culture, all while enjoying the stunning natural surroundings.

Things to do near Cheshire

Cheshire, Massachusetts, is perfect for adventure seekers and outdoor enthusiasts, offering thrilling activities like skiing at local ski resorts and ski fields. Visitors can explore various attractions, enjoy outdoor adventures, and consider a trip to nearby Chester for more entertainment options. Whether you crave adrenaline or scenic views, Cheshire has something to satisfy every adventurer's spirit.

Shopping

In Cheshire, visit the North Adams Center, a shopping hub with a vibrant city and family atmosphere located 16.1km away. If you're up for a drive, check out the North Adams Gateway Center and Colonial Plaza, both offering a delightful mix of shops in a friendly environment, also 16.1km away.

Recreation

Experience a round of golf at Skyline Country Club, where outdoor vibes enhance your play. For relaxation, visit Windsor Lake Park, a serene spot perfect for unwinding. Another great golfing option is Waubeeka Golf Links, offering beautiful landscapes and sports activities.

Adventure

At Jiminy Peak Mountain Resort, enjoy thrilling skiing and snowboarding on well-groomed trails, with vibrant sports vibes. Berkshire East Ski Resort offers exhilarating outdoor adventures and diverse ski options. Skyline Trail invites you to hike through breathtaking scenery, immersing you in the beauty of nature and adventure.

Nightlife

In Cheshire, the Williamstown Theatre Festival offers a captivating mix of romance and culture just 12.9km away, while the Adams Theater is only 8.0km away, providing a similar enchanting experience. For thrill-seekers, the Mountain Coaster, located 11.3km away, adds an exciting twist to the nightlife.

Booking tips and Expedia advantages for Cheshire

To save money on your trip to Cheshire, Massachusetts, consider visiting during the cheaper months of March to April or November, and aim for a Tuesday stay, which is the least expensive day. Use Expedia's search tool to compare room rates and find exclusive discounts by arranging results from lowest to highest price. Combine your hotel, flights, and activities for additional savings through package deals. For transportation, explore the area on foot or utilize the affordable public transport options available to keep costs down while enjoying your visit.

• 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 refine 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 deal.

Find the best attractions near Cheshire

Cheshire, Massachusetts, is perfect for outdoor enthusiasts and families seeking adventure. Visitors can explore the local library, hike the nearby mountains, or enjoy the serene beauty of nature reserves. With a blend of cultural experiences and recreational activities, Cheshire offers a delightful getaway for those looking to connect with nature and enjoy family-friendly attractions.

• Mount Greylock: Experience the breathtaking views from the highest peak in Massachusetts, perfect for hiking and outdoor adventures. Enjoy the stunning scenery that changes with the seasons, offering a unique backdrop for nature lovers and thrill-seekers alike.
• Mount Greylock State Reservation Visitor Center: A great starting point for families and outdoor enthusiasts, this visitor center provides information on trails and activities. Explore the surrounding wilderness, picnic areas, and educational exhibits that showcase the area's natural beauty and history.
• Williams College: Immerse yourself in the rich cultural atmosphere of this historic college, known for its beautiful campus and impressive art collections. Enjoy a stroll through the picturesque grounds and discover the vibrant academic community that thrives here.

Best time to go to Cheshire

The best time to visit Cheshire is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately 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	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

When planning your visit to Cheshire, Massachusetts, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is located 80.5km away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. Albany International Airport (ALB) in Albany, NY, is 56.3km away, offering accommodations such as the Park Manor Hotel, 12.9km from the airport. The closest option is Pittsfield Municipal Airport (PSF), situated 19.3km from Cheshire, with hotels like The Central Downtown Inn & Suites, just 3.2km away. Each airport provides convenient access to nearby lodging for a comfortable stay.