Book Hotels in Cheshire, MA
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Top Cheshire hotels
The Williams Inn
A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff.
Reviewed on Feb 7, 2026
The Yankee, Trademark Collection by Wyndham
All of the above plus its consistency. Reliable stay every time.
Reviewed on Feb 11, 2026
Berkshire Mountain Lodge
Perfect location, big rooms, nice staff.
Reviewed on Feb 10, 2026
Berkshires Untold
This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place!
Reviewed on Feb 10, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The room was beautiful - great for our family. Plenty of room and we enjoyed the gurgling brook out back! The pool was great along with the hot tub. Although the hot tub was supposed to be adult only, it was not enforced unless we left to request someone to do it. The bar near the pool area was fun ...
Reviewed on Feb 8, 2026
Vacation Village in the Berkshires
Excellent location and terrific space and amenities.
Reviewed on Feb 11, 2026
Hotel Downstreet, an Ascend Collection Hotel
Staff was friendly. The pool was nice. The room was a good size and very clean and comfortable.
Reviewed on Feb 10, 2026
The Red Lion Inn
Love the warmth and lobby’s wood-burning fireplace. Some of the amenities could be updated (EV chargers were broken, the fitness center was messy and missing weights) but there are few inns this charming in New England, and at this price level.
Reviewed on Feb 8, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Bathroom had somebody’s hair on the door and shower
Reviewed on Feb 9, 2026
Cheshire Hotel & Travel Guide
Within a 6-mile (10-kilometer) distance of the hustle and bustle of Cheshire, with Travelocity's reservations page you can choose from a small, but excellent offering of accommodations. With 4 places to stay on Travelocity within a 6-mile (10-kilometer) sweep of the city center, it shouldn't be hard to find a place suitable.
Travelocity-listed hotels that are located within a short drive of Cheshire include the The Spring's Inn and The Weathervane Motel.
Check out the Rookwood Inn and also the Gateways Inn & Restaurant. The Rookwood Inn is situated 16 miles (25 kilometers) outside of the main part of Cheshire. The Gateways Inn & Restaurant, can be found just 16 miles (25 kilometers) away. The Hampton Terrace Inn along with the Cranwell Spa and Golf Resort are two other Travelocity-listed accommodation options worth looking into in Cheshire.
If you have the time, why not spread your wings and explore the many attractions dotted around Western Massachusetts while you are here? Fall in love with Western Massachusetts's mountains and rolling hills. You should also venture to a few of its history museums. In this area of United States of America adventurous travelers may also enjoy skiing and cross-country skiing.
20 miles (32 kilometers) away from Cheshire, you'll find Lee, where you can spend a few hours exploring Lee Prime Outlets and Tyringham Cobble. When you spend a few nights in Lee, be sure to check out the Black Swan Inn, an Ascend Collection Hotel and Chambery Inn. Alternatively, you could stay in Lenox, 15 miles (24 kilometers) southwest of Cheshire, where you have the options of the Birchwood Inn and Hampton Inn & Suites Berkshires Lenox. The Shakespeare and Company and Tanglewood Music Center are other popular places to check out when in Lenox.
If you are into sports and enjoy attending thrilling games you could spend a day at Times Union Center, which can be found 30 miles (50 kilometers) to the west of Cheshire. Book accommodation right in the thick of the sporting action at the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.
Situated 35 miles (57 kilometers) outside Cheshire's center is Albany International Airport. Find nearby rooms at Albany Marriott or Homewood Suites by Hilton Albany.
Top reasons for your vacation to Cheshire
- Thrilling Skiing Adventures: Cheshire, Massachusetts is a premier destination for family ski vacations. Hit the slopes at local ski resorts and experience the thrill of skiing down snowy mountains.
- Breathtaking Scenic Lakes: Take in the stunning views of nearby lakes as you ski, creating a picturesque backdrop for your adventures.
- Tranquil Cheshire Countryside: Embrace the tranquility of nature as you explore the charming Cheshire countryside, surrounded by serene forests and parks.
- Nearby City Excursions: Visit nearby cities like Pittsfield and North Adams for a change of pace. Enjoy shopping, dining, and immerse yourself in cultural experiences.
- Cozy Small-Town Vibes: Experience the welcoming atmosphere of Cheshire, a charming small town that offers a perfect blend of outdoor excitement and cozy vibes for a memorable ski vacation.
Find your favorite hotels in Cheshire
If you're planning a ski vacation in Cheshire, Massachusetts, you'll find a variety of hotel accommodations to choose from. Whether you're looking for a cozy lodge, a family-friendly resort, or a luxurious hotel, there are options to suit every traveler's preference. Many hotels in Cheshire offer amenities such as pools, spas, and on-site dining. To make the most of your stay, be sure to check out hotel reviews to find the perfect fit for your family's needs.
| Hotel name | Type | Stars | Description |
| Harbour House Inn | Bed & breakfast | 3.5 | This 3.5-star Bed & Breakfast is a great option for your ski vacation in Cheshire, Massachusetts. Located in close proximity to various recreational activities such as horseback riding, fishing, and mountain biking, this hotel offers plenty of opportunities for outdoor adventure. Additionally, its convenient location makes it accessible to the wedding venues, boating facilities, and beautiful gardens in the area. With its free breakfast and no smoking policy, Harbour House Inn ensures a comfortable and enjoyable stay for you and your family. |
Explore the best activities and sights in Cheshire
Cheshire, Massachusetts is the perfect destination for a family ski vacation. With its close proximity to family-friendly activities, there's something for everyone to enjoy. Hit the slopes at the local ski resorts and spend quality time together as you glide down the snowy mountains. If skiing isn't your thing, explore the charming town and indulge in some shopping or dining. Take a hike in the nearby forest parks and admire the stunning natural beauty. Don't miss out on the chance to spot wildlife and enjoy the serene lakeside views. Cheshire is the ultimate destination for a memorable family ski vacation.
- St Mary's of the Assumption Church: St Mary's of the Assumption Church is a charming point of interest that embodies the beauty of nature and the rich cultural heritage of Cheshire. Situated amidst breathtaking mountains and scenic hiking trails, this church offers a peaceful retreat for visitors seeking a spiritual experience. The serene lake nearby provides a tranquil backdrop, perfect for reflection and contemplation. Additionally, the church is located close to a renowned university, making it an ideal spot for those interested in exploring the academic and intellectual side of the town. Whether you're interested in immersing yourself in nature, attending an opera performance, or simply admiring the picturesque scenery, St Mary's of the Assumption Church promises a unique and unforgettable experience.
Where to stay in Cheshire
Prepare for a delightful ski vacation in Cheshire, Massachusetts, where you and your family can indulge in thrilling activities, breathtaking scenery, and a welcoming small-town atmosphere. As you hit the slopes, take in the stunning views of the nearby scenic lakes, creating a picturesque backdrop for your skiing adventures. Afterward, explore the charming Cheshire countryside and embrace the tranquility of nature. For a change of pace, consider visiting the nearby cities, such as Pittsfield and North Adams, where you can enjoy shopping, dining, and cultural experiences. Cheshire offers the perfect blend of outdoor excitement and cozy small-town vibes for an unforgettable ski vacation.
- Lenox: Lenox is a charming city located 15.5 miles away from Cheshire. It is known for its beautiful gardens, museums, and live music scene. Families can explore the rich art and architecture, enjoy hiking in the scenic surroundings, and visit the local library. Lenox offers a unique blend of entertainment and tranquility, making it a perfect destination for a ski vacation with your family.
- Pittsfield: Located just 9.1 miles away from Cheshire, Pittsfield is a vibrant city with a rich historical background. It offers a variety of activities for families, including baseball games, sports events, theater performances, and opera shows. Families can also visit museums, enjoy biking around the city, and spend time by the lake. With its proximity to ski resorts, Pittsfield is an excellent choice for a ski vacation with a mix of cultural and outdoor experiences.
- Williamstown: Situated 10.6 miles away from Cheshire, Williamstown is a picturesque city known for its university and art scene. Families can explore the museums, go hiking in the nearby mountains, and enjoy ski activities. The city also offers theater performances, a library, and various entertainment options. With its family-friendly atmosphere and stunning scenery, Williamstown is a great choice for a ski vacation that combines cultural experiences with outdoor adventures.
The travel seasons of Cheshire
Trips to Cheshire show a small change in popularity throughout the year. The peak season to visit is from June to August, with July being the highest month. Off-peak season starts from November to January, and December sees the least travelers.
Cheshire has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 67.6 degrees Fahrenheit. The wettest month in Cheshire is July, so pack accordingly.
 Calendar Month |  Temperature |  Precipitation |  Cloudiness |
| January | 19.9°F (-6.7°C) | Light Rain | Mostly Cloudy |
| February | 22.1°F (-5.5°C) | Light Rain | Mostly Cloudy |
| March | 29.7°F (-1.3°C) | Light Rain | Mostly Cloudy |
| April | 41.4°F (5.2°C) | Light Rain | Mostly Cloudy |
| May | 53.8°F (12.1°C) | Light Rain | Mostly Sunny |
| June | 61.5°F (16.4°C) | Light Rain | Mostly Sunny |
| July | 67.6°F (19.8°C) | Light Rain | Mostly Sunny |
| August | 65.7°F (18.7°C) | Light Rain | Mostly Sunny |
| September | 58.6°F (14.8°C) | Light Rain | Mostly Sunny |
| October | 47.7°F (8.7°C) | Light Rain | Mostly Cloudy |
| November | 35.4°F (1.9°C) | Light Rain | Mostly Sunny |
| December | 27.0°F (-2.8°C) | Light Rain | Mostly Cloudy |
How do I find a great hotel with Travelocity?
Ensure your whole crew enjoys an unforgettable vacation. Utilize our family-friendly badge to find hotels that offer extra amenities for children. Take advantage of our custom filters to narrow down options, choosing hotels closest to popular attractions, with enhanced cleaning measures, and within your budget. Trust our reliable online travel platform for a seamless booking experience.
Why should I book with Travelocity?
Conference calls, to-do lists, and, of course, football practice. Busy lives and packed schedules call for hassle-free trips. Our aim is to provide worry-free travel every time you and your family book with us, so you can spend less time fretting and more time creating cherished memories. With our assistance, you can discover and plan your ideal journey, benefiting from transparent pricing, reliable reviews, and 24/7 guaranteed customer support before, during, and after your vacation.
How can I save money on my trip to Cheshire?
Avoid the peak season from June to August when planning your trip to Cheshire. This is when prices are higher and attractions are more crowded. To save money, consider bundling your flights, hotel, and car bookings as a package deal. Three inexpensive activities you can enjoy in Cheshire are hiking in the beautiful nature trails, exploring the local shops for budget-friendly shopping, and taking your family for a picnic by the serene lakeside.
Frequently asked questions
Recent Cheshire hotel reviews by fellow wanderers
Vacation Village in the Berkshires
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