Cheshire Hotels

Top reasons to visit Cheshire

• Outdoor Adventures: Cheshire is a haven for outdoor enthusiasts, offering skiing, championship golf courses, and the scenic Cheshire Cycleway for cycling.
• Charming Countryside: Explore picturesque views and quaint towns that define the stunning Cheshire countryside.
• Cultural Experiences: Discover local arts centres, libraries, and unique boutique shops that celebrate the region's vibrancy.
• Family-Friendly Activities: Cheshire caters to all travellers, providing a range of activities suitable for families and couples.
• Diverse Accommodation: Choose from various resorts and hotels, ensuring a comfortable stay tailored to your needs.

Find great hotels near Cheshire

Explore a range of delightful accommodation options in Cheshire, Massachusetts, perfect for families, romantics, and adventure seekers alike. With a variety of resorts and hotels available, visitors can enjoy essential amenities such as gyms and unique lodging experiences. Whether you’re seeking a group stay or an intimate getaway, Cheshire offers something for everyone to ensure a memorable vacation.

• Holiday Inn & Suites Pittsfield-Berkshires by IHG: Situated 14.5km from Cheshire, this 3-star hotel is perfect for adventurers seeking a vibrant city-themed getaway. With a focus on inclusivity, it warmly welcomes LGBTQIA travellers. Guests can enjoy a range of adventure sports and recreation activities both onsite and nearby, including horse riding, hiking, fishing, and skiing. Located in the city centre, the hotel provides easy access to local attractions, making it an ideal base for those looking to explore the Berkshires.
• Club Wyndham Bentley Brook: Located 9.7km from Cheshire, this 3-star hotel is tailored for those craving a thrilling ski vacation. With ski shuttles and lifts within a short distance, it is a ski lover's paradise. Guests can indulge in onsite snowboarding or venture out for cross-country skiing and hiking. The hotel's picturesque setting and cosy amenities make it a perfect retreat for adventure enthusiasts looking to embrace the winter wonderland.
• Hotel Downstreet, Ascend Hotel Collection: Just 16.1km from Cheshire, this 3-star hotel is a haven for pet lovers and LGBTQIA guests alike. With a welcoming pet policy that accommodates dogs and cats, it ensures that your furry friends can join the fun. The hotel features comfortable rooms and a friendly atmosphere, making it a great choice for those travelling with pets. Its affiliation with LGBTQI travel guides highlights its commitment to inclusivity and comfort for all guests.

Where to stay near Cheshire

Cheshire offers a delightful mix of adventure and romance, perfect for families and couples alike. Explore the stunning Cheshire countryside, filled with picturesque views and charming towns. Discover the boutique allure that defines this region, where you can indulge in local shops and cafes. Whether skiing in winter or enjoying the scenic beauty in summer, Cheshire promises a memorable getaway that captures the essence of outdoor exploration and tranquil retreats.

• Williamstown: Nestled 17.7km from Cheshire, Williamstown is a charming city renowned for its scenic beauty and vibrant cultural scene. The town attracts visitors throughout the year, with peak activity from April to June and July. It is a haven for ski enthusiasts and adventure seekers, boasting excellent ski fields and resorts. Highlights include the historic college university, picturesque mountains, and serene lakes that provide both recreational opportunities and stunning views. Whether you're hitting the slopes or exploring the local art and history, Williamstown offers a fulfilling travel experience.
• Pittsfield: Located 14.5km from Cheshire, Pittsfield is a lively city that draws adventure lovers year-round, particularly from June to August. Known for its thrilling outdoor activities, the city features ski resorts and fields that cater to both beginners and experienced skiers. Visitors can enjoy nearby lakes and mountains, which provide a beautiful backdrop for hiking, boating, and relaxation. Additionally, the local water park offers family-friendly fun, making Pittsfield an ideal destination for travellers seeking both adventure and leisure.
• North Adams: Situated 16.1km from Cheshire, North Adams is a captivating city that thrives on its outdoor offerings and artistic flair. With a peak in visitor numbers from June to July and September, the city is perfect for those seeking adventure and cultural experiences. North Adams is home to exceptional ski fields and resorts, while local attractions include an art museum and vibrant public art displays. The cultural centre adds to the city's charm, making it a fantastic spot for both outdoor enthusiasts and art lovers looking to explore the creative side of Massachusetts.

Things to do near Cheshire

Cheshire offers a delightful blend of outdoor adventures, making it perfect for skiing enthusiasts and thrill-seekers alike. Visitors can enjoy the nearby ski resorts and fields, alongside championship golf courses for a more relaxed day. The Cheshire Cycleway provides a scenic route for cycling aficionados looking to explore the natural beauty of the area. Whether you're hitting the slopes or enjoying a round of golf, Cheshire promises a memorable holiday experience.

Shopping

In Cheshire, you can enjoy shopping at local spots like the North Adams Center, North Adams Gateway Center, and Colonial Plaza, each offering a mix of business and family vibes, all located 16.1km away. If you're up for a drive, these centres make for a delightful shopping experience.

Recreation

At Skyline Country Club, enjoy a round of golf amidst scenic outdoors, just 8.0km from Cheshire. Windsor Lake Park, located 14.5km away, provides a serene environment for relaxation and wellness activities. Additionally, the Williams College Taconic Golf Course offers another splendid golfing experience, 16.1km from Cheshire.

Adventure

Experience exhilarating skiing at Jiminy Peak Mountain Resort, located 11.3km from Cheshire, where you can enjoy the thrilling slopes. For a blend of adventure and stunning outdoor scenery, explore the Broad Brook Trailhead, situated 20.9km away, perfect for hiking enthusiasts seeking natural beauty.

Nightlife

In Cheshire, the nearby Williamstown Theatre Festival offers a delightful mix of culture and romance, perfect for an entertaining evening. The Adams Theater, with its family-friendly atmosphere, is also a charming option. For a more adventurous night, the Alpine Super Slide promises fun just a short drive away.

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 and November, with Tuesday being the least expensive day to stay. Avoid weekends, especially Saturdays, which tend to be pricier. Use Expedia to find tailored accommodation options, applying filters for eco-friendly hotels and sorting by price for the best deals. Additionally, bundling your hotel, flights, and activities can lead to significant savings. Explore free local attractions to further stretch your budget while enjoying your stay in Cheshire.

• 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: Utilise Expedia’s search tool to tailor your options according to your budget, preferred location, and desired type of accommodation. For instance, selecting the Eco-certified filter will reveal sustainable and environmentally-friendly hotels that are currently available. To find the most affordable prices and offers, simply sort the price filter from low to high.
• Consider bundling your trip: You can enjoy savings by combining your hotel reservation in Cheshire with your flights and activities through an Expedia package.

Find the best attractions near Cheshire

Cheshire, Massachusetts offers an ideal setting for ski, adventure, and outdoor enthusiasts. Visitors can explore a variety of attractions including the local library, scenic mountains, and vibrant arts centres. Whether you're seeking cultural experiences, outdoor activities, or family-friendly adventures, Cheshire has something to cater to every kind of traveller, ensuring a memorable holiday filled with exploration and enjoyment.

• Mount Greylock: Experience stunning panoramic views from the highest peak in Massachusetts, perfect for outdoor enthusiasts. Enjoy hiking trails that lead through lush forests and scenic landscapes, showcasing the natural beauty of the Berkshires.
• Mount Greylock State Reservation Visitor Center: This visitor centre offers a gateway to adventure, with educational exhibits about the park’s ecology and history. It's an ideal starting point for families looking to explore the surrounding wilderness.
• Williams College: Delve into the rich cultural heritage of this prestigious institution. Stroll through its historic campus, admire the architecture, and visit the Williams College Museum of Art for a taste of exquisite exhibitions.

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

Cheshire, Massachusetts, is conveniently accessible via three major airports. Bradley International Airport (BDL) in Hartford, CT, is around 80.5km distant, with nearby hotel options like the DoubleTree by Hilton Hartford—only 1.6km away—and the Marriott Hartford Downtown, situated 19.3km from the airport. Albany International Airport (ALB) is approximately 56.3km away, with excellent hotels such as the Park Manor Hotel and The Landing Hotel at Rivers Casino, both 12.9km from ALB. The closest option is Pittsfield Municipal Airport (PSF), merely 19.3km from Cheshire, where you can find the luxurious Miraval Berkshires Resort & Spa just 9.7km away, offering limited shuttle services to the airport.