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Top Pittsfield hotels
Hotel On North
"Great location, clean room!"
Reviewed on Sep 14, 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
"Left wake up calls for 8 AM every day. Got one call at 8 and one at 7:30. So, didn't get one for 5 days."
Reviewed on Sep 17, 2026
Hilton Garden Inn Lenox Pittsfield
"Hotel was very clean, spacious, and staff was very courteous. Bar and restaurant onsite are hood, Guidos market is right in front and is AMAZING!! Definitely a great value and comfortable!"
Reviewed on Sep 14, 2026
Best Western Plus Berkshire Hills Inn & Suites
"I checked in at 2:15pm on Wednesday and around 8pm my daughter had a bedbug crawling on her. I had the front desk clerk come to the room. She was not helpful at all and instead of apologizing for it she asked me if I brought them with me. Then the manager came and she asked the same thing. This was ..."
Reviewed on Sep 13, 2026
The Central Downtown Inn & Suites
"It was priced well. The central location was convenient. The space inside was much larger than usual. There was a bedroom, living room and dining room combo with a full kitchen. It appears that it was an apartment at one time."
Reviewed on Sep 7, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
"Nice place, would stay again"
Reviewed on Sep 15, 2026
FairBridge Inn Express
"It's a pretty shoddy place. The staff was nice enough, but the whole facility could use a coat of paint. Our non-smoking room was definitely a smoking room at some point. Given how close it is to the Berkshires the price is appealing, but it's not as nice as their internet photos. It's sketchy."
Reviewed on Sep 14, 2026
Berkshire Mountain Lodge
Berkshire Inn
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Pittsfield Hotel & Travel Guide
Visitors to The Berkshires are in the ideal position when it comes to start researching the perfect hotels in Pittsfield. Spend some time comparing the 21 accommodation alternatives on Travelocity, all of which can be found within a 6-mile (10-kilometer) radius of the city's heart.
See the attractions by the commercial district of Pittsfield. Travelocity-listed hotels in the district include Berkshire Inn and Heart of the Berkshires Motel.
Travelocity's extensive database contains only a few economical lodgings in Pittsfield. The Econo Lodge is one of them.
8 miles (12 kilometers) from the middle of Pittsfield, you can find the Rookwood Inn. Alternatively, the Gateways Inn & Restaurant can be found about 8 miles (12 kilometers) away. Alternate places to rest your head include the Hampton Terrace Inn and the Cranwell Spa and Golf Resort.
After you've seen Pittsfield, you should leave time to explore the diverse activities of the Western Massachusetts area. Western Massachusetts proudly offers mountains. Interesting traveler sites are history museums. Visitors in this section of United States of America can enjoy skiing.
Looking for activities? Spend a few hours discovering Mount Greylock State Reservation Visitor Center and Skyline Country Club, which can be found in Lanesborough, 6 miles (10 kilometers) to the northeast of Pittsfield. If you head to Lanesborough, be sure to check out the The Weathervane Motel and Lanesborough Country Inn. Alternatively, you could stay in Williamstown, 14 miles (22 kilometers) north of Pittsfield, where you can choose between the The Spring's Inn and Berkshire Hills Country Inn. While in Williamstown, be sure to explore the Williams College and Williams College Museum of Art.
Simply because you're on vacation, who is to say that you can't fuel your love of all things sport. Find Times Union Center 25 miles (43 kilometers) to the northwest of Pittsfield. Book Travelocity-listed accommodation near the action at the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.
Albany International Airport is a commonly used airport, and is situated 35 miles (53 kilometers) away from Pittsfield. Accommodation options nearby are Albany Marriott and Homewood Suites by Hilton Albany.
Top reasons for your vacation to Pittsfield
- Tanglewood Music Center: Enjoy outdoor concerts and events at this renowned music center.
- Skiing and Snowboarding: Experience the thrill of skiing and snowboarding at nearby resorts.
- Museums and Historical Sites: Explore the rich history of Pittsfield through its museums and historical sites.
- Great Barrington and Western Massachusetts: Discover the nearby cities known for their rich history and stunning landscapes.
- Local Shopping Centers: Indulge in some retail therapy and find unique gifts and souvenirs.
Find your favorite hotels in Pittsfield
If you're planning a ski vacation in Pittsfield, Massachusetts, you'll find a variety of hotels to choose from. Whether you're looking for luxury accommodations or cozy lodges, there are options to suit every preference and budget. These hotels provide convenient access to the ski slopes and other attractions in the area. With their comfortable amenities and friendly service, they offer the perfect place for you and your family to relax and enjoy your winter getaway.
| Hotel name | Type | Stars | Description |
| Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel | Hotel | 3.0 | This 3.0-star rating hotel is conveniently located near museums, library, indoor pool, wedding venues, theaters, massage facilities, saunas, and ski resorts. With friendly staff and nearby cafes, it offers a comfortable and enjoyable stay for your ski vacation. |
| Berkshire Mountain Lodge | Lodge | 3.0 | A 3.0-star rating lodge, it is in close proximity to baseball, sports, entertainment, theaters, operas, museums, biking trails, lakes, and ski areas. With a touch of history, this lodge is an ideal option for your ski vacation. |
| Best Western Plus Berkshire Hills Inn & Suites | Hotel | 2.5 | This 2.5-star rating hotel is known for its friendly staff and convenient location near ski resorts, fitness centers, urban areas, sports facilities, breakfast options, and relaxing amenities. It offers a complimentary breakfast and is suitable for business and leisure travelers. |
Explore the best activities and sights in Pittsfield
Planning a ski vacation in Pittsfield, Massachusetts? You're in for a treat! This charming town offers a range of family-friendly activities and attractions. Nearby, you'll find top landmarks like the Tanglewood Music Center, where you can enjoy outdoor concerts and events. If you're looking for outdoor adventures, Pittsfield has plenty to offer, including skiing and snowboarding at nearby resorts. The area also boasts a rich history, with museums and historical sites to explore. Whether you're seeking cultural experiences, outdoor fun, or both, Pittsfield has something for everyone in the family to enjoy.
- Bousquet Ski Area: Bousquet Ski Area is a picturesque ski destination nestled in a small town. This family-friendly point of interest offers thrilling sports experiences for all ages. Enjoy the scenic beauty of the surrounding nature while skiing or snowboarding down the slopes. The area also features a charming lake, perfect for a leisurely stroll or a relaxing picnic. After a day of outdoor adventures, unwind with some entertainment at the nearby opera house. Bousquet Ski Area is the ideal spot for nature lovers and outdoor enthusiasts looking for an unforgettable skiing experience in a serene and friendly environment.
- Hancock Shaker Village: Immerse yourself in the rich history and culture of this small town gem, Hancock Shaker Village. Wander through the beautifully preserved village, admiring the historical buildings and gardens. Explore the fascinating museums that showcase the Shaker lifestyle and traditions. Take a peaceful hike in the surrounding hills, enjoying the serene natural beauty. For a touch of entertainment, catch a performance at the opera house. Hancock Shaker Village is a place where history comes alive, offering a unique opportunity to step back in time and experience the charm and tranquility of a bygone era.
- Pittsfield State Forest: Embark on an adventurous journey at Pittsfield State Forest, a national state park. This family-friendly destination offers a wide range of activities surrounded by breathtaking natural beauty. Discover scenic hiking trails that lead to stunning viewpoints and encounter diverse wildlife along the way. For those seeking a thrilling outdoor experience, try your hand at biking through the forest. After a day of adventure, indulge in some shopping and dining in the nearby town. Pittsfield State Forest is the perfect getaway for nature lovers and adventure seekers, providing a refreshing escape into the great outdoors.
Where to stay in Pittsfield
Get ready for an exhilarating ski vacation in Pittsfield, Massachusetts! Located in Berkshire County, this charming town offers a plethora of affinities for you and your family to enjoy. Firstly, you can explore the nearby cities of Great Barrington and Western Massachusetts, which are known for their rich history and stunning landscapes. Secondly, indulge in some retail therapy at the local shopping centers, where you can find unique gifts and souvenirs. Lastly, don't miss the opportunity to hit the slopes and experience the thrill of skiing in the picturesque mountains of Pittsfield. Get ready for a memorable winter getaway!
- Lenox: Lenox is a charming city located 6.5 miles away from Pittsfield. It offers a unique experience with its beautiful gardens, museums, yoga studios, live music venues, and entertainment options. The city is also known for its scenic views, art galleries, and architectural wonders. Families can enjoy hiking in the surrounding nature trails and visit the local library for a quiet afternoon. Lenox is a perfect destination for a ski vacation with your family, as it offers a diverse range of activities and attractions for all ages.
- Williamstown: Williamstown, situated 18.4 miles away from Pittsfield, is a vibrant city known for its prestigious university and rich art scene. Families can visit museums, go hiking in the nearby mountains, and even enjoy skiing during the winter season. The city also offers a family-friendly atmosphere with libraries, entertainment options, and picturesque scenery. Williamstown is an ideal destination for a ski vacation with your family, as it combines outdoor adventures with cultural experiences.
- Great Barrington: Great Barrington, located 18.3 miles away from Pittsfield, is a lively city known for its rock climbing spots, hiking trails, and live music venues. Families can enjoy the beautiful scenery, visit charming cafes and restaurants, and experience the local dining scene. The city also offers entertainment options such as theaters and flower festivals. Great Barrington is a perfect choice for a ski vacation with your family, as it provides a mix of adventure, relaxation, and cultural experiences.
The travel seasons of Pittsfield
Trips to Pittsfield show no 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 October to December, and December sees the least travelers.
Pittsfield 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 70.3 degrees Fahrenheit. The wettest month in Pittsfield is October, so pack accordingly.
 Calendar Month |  Temperature |  Precipitation |  Cloudiness |
| January | 22.6°F (-5.2°C) | Light Rain | Mostly Cloudy |
| February | 24.6°F (-4.1°C) | Light Rain | Mostly Cloudy |
| March | 32.4°F (0.2°C) | Light Rain | Mostly Cloudy |
| April | 44.2°F (6.8°C) | Light Rain | Mostly Cloudy |
| May | 56.3°F (13.5°C) | Light Rain | Mostly Sunny |
| June | 64.0°F (17.8°C) | Light Rain | Mostly Sunny |
| July | 70.3°F (21.3°C) | Light Rain | Mostly Sunny |
| August | 68.4°F (20.2°C) | Light Rain | Mostly Sunny |
| September | 61.3°F (16.3°C) | Light Rain | Mostly Sunny |
| October | 50.0°F (10.0°C) | Light Rain | Mostly Sunny |
| November | 37.6°F (3.1°C) | Light Rain | Mostly Sunny |
| December | 29.3°F (-1.5°C) | Light Rain | Mostly Cloudy |
Food and dining in Pittsfield
If you're a food lover visiting Pittsfield, Massachusetts, you're in for a treat. The city is surrounded by scenic woods, providing a beautiful backdrop for your culinary adventures. Start your day with a delicious breakfast at Highland Restaurant, known for its highly rated North American dishes. For lunch, head to Panera Bread for a variety of fresh sandwiches and salads. In the evening, you can enjoy a dining experience at your hotel or explore numerous restaurants in the neighborhood. Don't forget to try the famous clam chowder, a local favorite. Applebee's and Friendly's are both popular options for moderately rated North American cuisine.
How do I find a great hotel with Travelocity?
Ensure that your entire crew enjoys an unforgettable vacation with our reliable and comprehensive online travel platform. Easily find the ideal accommodations by using our family-friendly badge, which identifies hotels offering extra amenities for children. Our custom filters make it effortless to narrow down options based on proximity to top attractions, enhanced cleaning measures, and price range.
Why should I book with Travelocity?
Conference calls, to-do lists, and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide worry-free travel every time you and your family book with us so that you can spend less time fretting and more time creating cherished memories. To that end, we will assist you in discovering and planning your ideal trip, along with offering transparent pricing and reliable reviews, as well as 24/7 guaranteed customer support before, during, and after your vacation.
How can I save money on my trip to Pittsfield?
Save money by visiting Pittsfield during the less popular October-December season. You can also bundle your flights, hotel, and car bookings to get a discounted price. For inexpensive local activities, consider visiting the baseball field for a game, exploring the museums to learn about the city's history, or enjoying biking around the beautiful lakes. These options provide affordable entertainment for the whole family.
Frequently asked questions
Recent Pittsfield hotel reviews by fellow wanderers
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
"I really love staying here. It’s no nonsense clean and i feel safe traveling as a woman alone… However they really need to step up their morning breakfast. I eat gluten free and they never have any. I’ve asked for ivermectin a month now and they just tell me they will mention it…."
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