Hotels in Pittsfield

Some of the best places to stay in Pittsfield are Lenox, Williamstown and Great Barrington. Lenox, Williamstown, and Great Barrington each offer unique charms for travelers. Lenox is known for its cultural attractions and elegant accommodations, making it ideal for first-time visitors. Williamstown features art museums and stunning landscapes, while Great Barrington boasts a vibrant downtown and outdoor activities. All three areas provide a range of hotel options, from cozy inns to modern hotels, ensuring a comfortable stay. Whether you seek luxury or budget-friendly accommodations, these towns cater to diverse traveler preferences. Here are some of the most popular hotels with our guests in Pittsfield:

1. LenoxOpens in a new window: Lenox is a charming destination known for its cultural attractions and entertainment options, making it a perfect spot for visitors interested in the arts. Highlights include the Tanglewood Music Center, a renowned concert venue, and The Mount, a historic house that showcases the literary heritage of Edith Wharton. For accommodation, consider 33 MainOpens in a new window, a 4.0-star bed and breakfast offering complimentary breakfast and entertainment options like cable TV. Another great choice is Garden Gables InnOpens in a new window, which provides a range of recreational activities like skiing and hiking, along with free breakfast. Lastly, Seven Hills InnOpens in a new window is a pet-friendly hotel, making it ideal for travelers with furry companions.
2. WilliamstownOpens in a new window: Williamstown is a cultural hub, home to Williams College and the Massachusetts Museum of Contemporary Art, offering a rich artistic experience. This town is perfect for those who appreciate history and modern art. The Williams InnOpens in a new window is a 4.0-star hotel catering to both business and pet-friendly travelers, featuring meeting rooms and amenities for furry friends. The Orchards HotelOpens in a new window, a 3.5-star hotel, is also ideal for families and adventurers, providing access to outdoor activities and business facilities. For a budget-friendly option, Stay BerkshiresOpens in a new window allows pets and offers essential amenities.
3. Great BarringtonOpens in a new window: Great Barrington is an outdoor enthusiast's paradise, with ski fields like Ski Butternut and Catamount Ski Area nearby, perfect for winter sports lovers. The town also hosts cultural attractions like the National Shrine of the Divine Mercy. For accommodation, The Old Inn On The GreenOpens in a new window is a 4.0-star inn that welcomes pets and provides a cozy atmosphere. The White HartOpens in a new window, another 4.0-star hotel, caters to business travelers while allowing pets, making it a convenient option for those traveling with pets. Finally, Rock Hall Luxe LodgingOpens in a new window offers a luxurious experience with business amenities and a pet-friendly policy, ensuring a comfortable stay.

Three days in Pittsfield offers travelers a chance to explore its beautiful lakes, scenic parks, and rolling hills. Enjoy outdoor activities like hiking, boating, and picnicking, while also catching local sports events and vibrant performances in theater and opera. It's a perfect getaway for nature and culture enthusiasts alike. Here's a quick itinerary to make the most of your trip to Pittsfield:

• Day 1: Begin your adventure at October Mountain State Forest, where you can immerse yourself in nature with hiking trails and stunning views. Afterward, take a short drive to Wood's Pond for a peaceful lakeside experience; consider bringing a picnic to enjoy by the water. Finish your day at the Lee Library, where you can explore local literature and perhaps attend a community event or workshop that enriches your understanding of the Pittsfield area.
• Day 2: Your day starts at the National Shrine of the Divine Mercy, a serene place offering reflection and spiritual rejuvenation. Next, visit the historic Mission House, which gives insight into the region's colonial history. Conclude your day at the Norman Rockwell Museum, where you can admire the iconic works of one of America’s most beloved illustrators, capturing the essence of everyday life.
• Day 3: Kick off your morning at The Mount, the elegant estate of author Edith Wharton, where beautiful gardens and insightful tours await. Then, head to Ventfort Hall Mansion and Gilded Age Museum to explore the opulent lifestyle of the early 20th century. Wrap up your day with a visit to Pleasant Valley Wilderness Sanctuary, where you can enjoy tranquil walking trails and perhaps catch a glimpse of local wildlife as the sun begins to set.

1. Book for the cheapest times: The most affordable times to visit Pittsfield are March, November, and December, when hotel rates are significantly lower. If you're traveling internationally, it's best to book your flight at least two months in advance to secure better prices. To fully enjoy the main attractions, including local museums and the scenic lake, plan to stay for at least 2-3 days. This way, you can experience all that Pittsfield has to offer while sticking to a budget, making your trip a great value for money.
2. Look for last-minute deals on Hotels.com: If you're looking for great last-minute hotel deals in Pittsfield, Hotels.com is a fantastic resource. To explore these offers, head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section on the site, where you could find discounted rates for hotels just before your travel date. Also, consider enabling email alerts or push notifications from Hotels.com to keep yourself informed about flash sales and special promotions, increasing your chances of snagging a great deal on your Pittsfield stay.
3. Be flexible with dates: Hotel prices can fluctuate due to factors like the location, star rating, and the time of year. Therefore, being flexible with your travel dates may help you save on hotel expenses in Pittsfield.
4. Consider your location: Staying in the city center and close to local attractions in Pittsfield is usually more expensive. If you opt for accommodations further away from downtown, you can take advantage of transportation options like cars and buses to explore the area, which can be more likely to be affordable.
5. Upgrade with One Key: Become a member of Hotels.com's free One Key rewards program when booking your stay in Pittsfield. Earn points for your hotel bookings and progress through Blue, Silver, Gold and Platinum tiers. Unlock a range of exclusive rewards, including room upgrades when available, discounted rates, and member-only offers. Join today.

Here are a few popular dining spots in Pittsfield, Massachusetts, United States of America:

• The Roasted Garlic: A beloved local gem, this restaurant offers a delightful menu that celebrates fresh, seasonal ingredients with a creative twist. Known for its inventive takes on classic dishes, The Roasted Garlic showcases the rich flavors of the region, often incorporating locally-sourced produce and artisanal products.
• Papa Joe's Ristorante & Pizzeria: This popular spot combines traditional Italian recipes with a modern flair, serving up mouthwatering pizzas and pasta dishes that reflect the area's culinary heritage. Their commitment to quality ingredients ensures a memorable dining experience that captures the essence of Italian-American cuisine.
• KOTO Hibachi Steak House: Specializing in the art of hibachi, KOTO offers an interactive dining experience where chefs prepare delicious meals right before your eyes. Their menu features a variety of fresh seafood and steak options, emphasizing bold flavors while honoring Japanese culinary traditions.