Hotels in Pittsfield

Pittsfield: Where Art Meets Nature in a Scenic Oasis

Nestled in the heart of the Berkshires, Pittsfield, Massachusetts, is a charming blend of culture and nature. Explore the vibrant downtown, where art galleries and local shops flourish alongside historical sites. Visit the renowned Berkshire Museum for a taste of local history and art, then unwind at picturesque Onota Lake, perfect for kayaking or a leisurely stroll. Embrace the scenic beauty of nearby parks and trails, ideal for hiking and outdoor adventures. With its rich history, artistic spirit, and stunning landscapes, Pittsfield is an inviting weekend getaway for those seeking both relaxation and inspiration. For our best hotel rates in Pittsfield and to enhance your stay, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Discover great hotels in Pittsfield

Pittsfield offers a variety of hotel accommodations, from cozy boutique hotels to comfortable chain options. Whether you prefer a charming B&B or a spacious suite, you'll find plenty of great places to stay in this vibrant city, perfect for exploring the beautiful Berkshires. Here are some of the best hotels in Pittsfield that our travelers love:

1. 33 MainOpens in a new window: 33 Main is a charming 4.0-star Bed and Breakfast that provides a delightful blend of comfort and hospitality. This property offers a variety of dining options, including complimentary full breakfast, ensuring a great start to your day. Guests can unwind with entertainment features like a flat-screen television and cable channels. Located near the city center and a historical district, 33 Main is perfect for leisure travelers seeking a picturesque experience. The reviews highlight its beautiful ambiance and excellent location, making it a perfect choice for those looking to return to a serene setting.
2. Garden Gables InnOpens in a new window: Garden Gables Inn stands out as a 4.0-star hotel with a focus on leisure travelers. This property boasts an array of dining options, such as free breakfast and couples dining experiences. With recreational activities like hiking and skiing nearby, it's an ideal retreat for adventure seekers. The hotel features modern entertainment amenities, including premium television channels and flat-screen TVs. Guests appreciate the beautiful rural and village views, along with its proximity to historical sites, creating a unique and enriching stay. Positive sentiments highlight its inviting atmosphere and excellent amenities.
3. The Central Downtown Inn & SuitesOpens in a new window: The Central Downtown Inn & Suites, a 4.0-star guesthouse, caters specifically to travelers looking for a pet-friendly experience. This property welcomes pets, offering a comfortable environment with amenities suited for animal lovers. With a spacious suite and a well-stocked kitchen, The Central Downtown Inn & Suites provides a home-like feel that appeals to leisure travelers. The effortless check-in and check-out process enhances convenience, allowing guests to enjoy their stay without stress. Positive reviews emphasize its cleanliness, value for money, and the enjoyable nearby dining options, making it a delightful choice for those exploring the Berkshires.

Top locations to stay in Pittsfield

When visiting Pittsfield, Massachusetts, great areas to stay in include Lee, Lenox, and Stockbridge. Stockbridge is renowned for its charming gardens and museums, while Lenox offers beautiful architecture and a vibrant library. Lee boasts scenic lakes and rich history. For first-time visitors, Stockbridge is best suited, given its diverse attractions and cultural experiences.

1. LeeOpens in a new window: Lee is a charming destination perfect for those who appreciate a cozy atmosphere enriched by local culture. With its historic churches and beautiful lakes, it's an ideal spot for relaxation. Check out the Norman Rockwell Museum and the scenic Housatonic River Walk for a delightful day out. For shopping enthusiasts, Lee Premium Outlets offers a variety of brand-name stores, making it easy to browse for great deals. Enjoy a leisurely stroll through the town's quaint streets, where you'll find unique shops and local art, creating a perfect blend of culture and community.
2. LenoxOpens in a new window: Lenox is a picturesque town that boasts stunning gardens and rich architectural heritage. It's home to the renowned Tanglewood Music Center, where you can catch a concert in a beautiful outdoor setting. The Mount, a historic home designed by Edith Wharton, adds a unique touch, showcasing exquisite architecture and lush gardens. For those who love reading, the town's libraries offer a peaceful retreat. The local shopping scene includes boutique stores and specialty markets, providing a delightful experience for visitors looking to take a piece of Lenox home.
3. StockbridgeOpens in a new window: Stockbridge is a quintessential New England town that's steeped in history and culture. The Norman Rockwell Museum is a must-visit, celebrating the iconic artist's work in a charming setting. Nature lovers will appreciate the beautiful gardens and the nearby National Shrine of the Divine Mercy, offering a serene escape. The town also features cultural attractions like Shakespeare and Company and Mahaiwe Performing Arts Center, providing a vibrant arts scene. With an array of unique shops and antique stores, Stockbridge is a fantastic choice for those looking to explore local craftsmanship while enjoying the picturesque surroundings.

Things to do in Pittsfield

Nestled amidst rolling hills and sparkling waters, Pittsfield offers a delightful mix of outdoor fun and vibrant entertainment. Enjoy leisurely days on the lake with boating or fishing, and soak up the natural beauty on scenic hikes. Evenings come alive with thrilling sports events and captivating performances, making it a must-visit destination for excitement and relaxation.

• Hancock Shaker VillageOpens in a new window – Step back in time at this historic village, where you can explore beautifully preserved buildings and learn about the unique Shaker way of life. Enjoy the lush landscapes and serene lake while engaging with interactive exhibits that showcase the community's craftsmanship and sustainable living practices.
• National Shrine of the Divine MercyOpens in a new window – Visit this serene shrine dedicated to the message of Divine Mercy. The peaceful grounds invite you to reflect and pray, with stunning architecture and beautiful gardens surrounding you. Don’t miss the opportunity to partake in daily masses and special events that foster spiritual growth.
• The MountOpens in a new window – Discover the former home of author Edith Wharton, nestled in picturesque gardens and offering breathtaking views of the Berkshires. Wander through the elegant interiors and lush landscape, each telling stories of Wharton's life and literary contributions.
• Berkshire MuseumOpens in a new window – Dive into the wonders of nature and art at this natural history museum. Explore fascinating exhibits that range from local wildlife to fine art, ensuring a fun and educational experience for visitors of all ages. The museum’s diverse collections will pique your curiosity!
• Pleasant Valley Wilderness SanctuaryOpens in a new window – Embrace the outdoors in this beautiful preserve where hiking trails wind through diverse ecosystems. Whether you're birdwatching, picnicking, or simply enjoying nature, the sanctuary offers a peaceful retreat perfect for escaping the hustle and bustle.

5 tips for savvy savings when booking a hotel in Pittsfield

1. Book for the cheapest times: The most budget-friendly times to visit Pittsfield are March, April, and November, when hotel prices are lower. To fully appreciate the city's historical and cultural offerings, a stay of at least 2 to 3 days is recommended. During your visit, you can explore various landmarks and attractions, such as local museums and the scenic lake, making this trip a great value for money for those on a budget. Given the seasonality, hotel rates might drop during these months, enhancing the affordability of your stay.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Pittsfield, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted hotel rates as your travel date approaches. Enabling email alerts or push notifications can keep you informed about flash sales and special promotions, helping you save on your stay. Additionally, the Smart ShoppingOpens in a new window tool available in the app allows you to compare hotel prices and amenities, making it easier to find the best hotel deal. With these features, you'll be among the first to know if prices drop or rooms become available for your last-minute getaway.
3. Be flexible with dates: Prices can fluctuate due to factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates may help you save on your stay in a Pittsfield hotel. If you're in search of something different, boutique hotels can provide a more personalized experience and sometimes offer better value. When you book through Hotels.com, we'll inform you if the price for your chosen dates is above or below the average. If the price is on the higher end, we'll suggest alternative dates that could be more affordable, helping you find the best deal.
4. Consider your location: Hotels near the city center usually tend to be more expensive, but with Pittsfield's outstanding public transportation options, you may discover a more affordable independent hotel a bit farther out that’s still well-connected. If you're interested in exploring alternative, less crowded neighborhoods or even some lesser-known nearby towns, you can often find great value for your money. Opting for these alternative destinations could provide a more authentic and budget-friendly experience.
5. Join One Key™: Become a One Key MemberOpens in a new window for free and book your next stay in Pittsfield. Save on over 100,000 hotels worldwide with exclusive member prices. As a member, you can quickly progress through the tiers and enjoy perks, like free room upgrades when available and food and beverage discounts at select VIP Access properties.

Best time to go to Pittsfield

Pittsfield experiences its lowest average temperature in January, at 22.6°F (-5.2°C), while July is the hottest month, with an average temperature of 70.3°F (21.3°C). October is typically the wettest month. If you’re looking to soak up the lively atmosphere in Pittsfield, June to August are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, accompanied by light rainfall. However, if you prefer a more relaxed experience, October to December are perfect for a quieter getaway, marked by light rainfall and mostly sunny to mostly cloudy conditions.