Find hotels in Pittsfield, MA from $68

These Pittsfield insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: September 2, 2026.

Top reasons to visit Pittsfield

• Outdoor Adventures: Experience skiing at local resorts and hiking through the scenic trails of Pittsfield State Forest.
• Historic Charm: Explore beautifully preserved historic houses and the vibrant downtown area that blends old-world charm with modern amenities.
• Scenic Beauty: Discover the stunning Berkshire Hills, perfect for outdoor activities and picturesque views.
• Family-Friendly Atmosphere: Enjoy neighborhoods that cater to families, romantic outings, and unforgettable experiences.
• Diverse Accommodations: Choose from a variety of hotels that offer options for every type of traveler.

Find great hotels in and around Pittsfield

Discover the charming city of Pittsfield, Massachusetts, where a variety of hotel accommodations await you. Whether you're seeking a family-friendly resort or a romantic getaway, you'll find options that cater to every type of traveler. Enjoy adventure-filled vacations or relaxing retreats at the best hotels in Pittsfield, designed to ensure a memorable stay. Explore the perfect lodging that suits your needs in this beautiful New England destination.

• The Yankee, Trademark Collection by Wyndham: The Yankee, Trademark Collection by Wyndham is a budget-friendly hotel with a guest rating of 9.2, ideal for business travelers seeking comfort and convenience. Situated 3 miles from Pittsfield, this hotel offers a practical yet inviting atmosphere. Amenities include complimentary Wi-Fi, a business center, and comfortable guest rooms designed for productivity and relaxation. Its proximity to local business hubs makes it a perfect choice for those on work-related trips, while the warm hospitality ensures a pleasant stay.
• Berkshire Mountain Lodge: Berkshire Mountain Lodge is a 3-star lodge with a guest rating of 9.0, perfect for adventure seekers and outdoor enthusiasts. Located in Pittsfield, this property boasts a unique ski and golf theme, catering to those looking for an exhilarating vacation experience. Guests can enjoy easy access to ski lifts and golf courses, as well as a range of adventure sports like hiking, kayaking, and ziplining. The lodge features cozy accommodations and recreational activities, making it an excellent choice for families and friends looking to explore the great outdoors.
• Holiday Inn & Suites Pittsfield-Berkshires by IHG: Holiday Inn & Suites Pittsfield-Berkshires by IHG is a 3-star hotel with a guest rating of 8.0, situated in the heart of Pittsfield. This family-friendly property offers a blend of adventure and city experiences, making it an ideal base for exploring the Berkshires. Onsite amenities include a fitness center, a restaurant, and family-oriented services such as cribs and breakfast options for children. Guests can engage in various activities nearby, including skiing, fishing, and biking, ensuring an exciting stay for all ages.

Where to stay near Pittsfield

Pittsfield, Massachusetts, offers a delightful blend of adventure and relaxation for every traveler. Explore the vibrant downtown, where historic charm meets modern amenities. Venture into the stunning Berkshire Hills for outdoor fun, whether skiing or hiking. Nearby neighborhoods provide a family-friendly atmosphere, romantic spots, and picturesque scenery, making it a perfect getaway for all. Discover the heart of Pittsfield and create unforgettable memories in this charming destination.

• Lenox: Located 7 miles from Pittsfield, Lenox is a charming town that attracts visitors with its blend of culture and outdoor activities. Known for its vibrant arts scene, Lenox hosts numerous music concerts and theater performances, making it a perfect stop for those seeking entertainment. The peak travel season from June to August sees an influx of couples and culture enthusiasts drawn to its romantic atmosphere. Outdoor lovers can enjoy the stunning local landmarks, including picturesque lakes and mountains. Don't miss the opportunity to relax at one of the event conference venues that frequently host seasonal events and gatherings.
• Lee: Just 10 miles from Pittsfield, Lee offers a delightful escape for families and couples alike. With a travel experience that remains relatively steady year-round, visitors flock here primarily during the summer months. Lee is known for its engaging entertainment options, including theaters and music concerts, as well as thrilling ski fields in the winter. The scenic beauty of local lakes and mountains provides a stunning backdrop for outdoor activities. History buffs can explore nearby monuments that reflect the town's rich heritage, making it an ideal destination for those seeking both adventure and culture.
• Hancock: Only 7 miles from Pittsfield, Hancock is a haven for adventure seekers and sports enthusiasts. With its travel peak occurring in the spring and summer months, this city is especially popular among skiing aficionados who come for its world-class ski resorts and fields. The breathtaking mountains and serene lakes that surround Hancock provide a perfect setting for outdoor exploration, whether you're skiing in winter or hiking in summer. The urban parks offer a relaxing spot to unwind after a day of adventure, making Hancock a must-visit for those looking to blend excitement with natural beauty.

Things to do in Pittsfield

Pittsfield, Massachusetts, offers a variety of activities for adventure seekers and sports enthusiasts. Enjoy skiing at local resorts and fields, or explore the scenic trails at Pittsfield State Forest for hiking. The city also features entertainment venues and event spaces, making it a great destination for both outdoor adventures and lively events. Dive into the local amenities and discover what makes Pittsfield a unique spot for your vacation.

Shopping

Pittsfield offers charming shopping options like the Berkshire Mall, featuring popular retail stores and dining. If you're up for a drive, head to the nearby Lee Premium Outlets for great deals on brand-name apparel and accessories.

Recreation

Experience tranquility at Canyon Ranch, where you can indulge in holistic treatments, fitness classes, and nutritious dining options. For rejuvenation, head to the Berkshire Yoga Dance and Fitness studio for yoga sessions that connect mind and body amidst serene surroundings.

Adventure

Visit Bousquet Mountain for thrilling skiing and snowboarding in winter, and mountain biking in summer. The nearby Pittsfield State Forest offers hiking trails with stunning views, perfect for nature lovers seeking adventure. Don't miss the serene beauty of Lake Onota for kayaking and fishing opportunities.

Nightlife

Pittsfield's nightlife offers a vibrant atmosphere with live music at The Colonial Theatre and craft brews at Big Elm Brewing. For a laid-back vibe, check out the Berkshire Museum's evening events or enjoy a cozy cocktail at The Lantern Bar & Grill, perfect for unwinding after a day of exploration.

Booking tips and Expedia advantages for Pittsfield

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Pittsfield 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 Pittsfield is Tuesday. The most expensive day to stay in Pittsfield is Saturday.
• Find cheap hotels on Expedia: Expedia’s search tool makes it easy to choose your budget, desired location, and additional preferences. You can sort the results to display hotels from the lowest to the highest price, helping you find the most affordable options first. Additionally, you can refine your search by hotel type; for instance, selecting the Eco-certified filter will show you sustainable and environmentally friendly hotels that you can book.
• Consider bundling your trip: You can save money by combining your hotel stay in Pittsfield with your flights and activities through an Expedia package deal.

Find the best attractions in and around Pittsfield

Pittsfield, Massachusetts, is an ideal destination for adventure seekers and sports enthusiasts, offering a variety of attractions. Explore the area's beautiful reserves, historic houses, and majestic mountains, perfect for outdoor activities and cultural experiences. Whether you’re skiing or delving into local history, Pittsfield has something for every traveler looking to create unforgettable memories.

• Hancock Shaker Village: Experience the unique lifestyle of the Shakers at this living history museum. Explore beautifully preserved buildings, engage with costumed interpreters, and enjoy tranquil gardens that reflect Shaker principles of simplicity and sustainability.
• National Shrine of the Divine Mercy: Nestled 11 miles from Pittsfield, this serene shrine offers spiritual reflection and stunning architecture. Visitors can participate in daily worship and appreciate the peaceful grounds that invite contemplation and prayer.
• Norman Rockwell Museum: Located 12 miles away, this art museum celebrates the beloved American illustrator Norman Rockwell. Explore his iconic works, enjoy rotating exhibits, and learn about his impact on American culture and art.

Best time to go to Pittsfield

The best time to visit Pittsfield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.6°F (-5.2°C)	Light Rain	Mostly Cloudy	Average	Average
February	24.6°F (-4.1°C)	Light Rain	Mostly Cloudy	Average	Average
March	32.4°F (0.2°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	44.2°F (6.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	56.3°F (13.5°C)	Light Rain	Mostly Sunny	Average	Average
June	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	70.3°F (21.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	68.4°F (20.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	61.3°F (16.3°C)	Light Rain	Mostly Sunny	Average	Average
October	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High
November	37.6°F (3.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	29.3°F (-1.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

The nearest major airports for your trip to Pittsfield

If you are visiting Pittsfield, Massachusetts, the closest major airports are Hartford, CT (BDL-Bradley Intl.), ALBany, NY (ALB-Albany Intl.), and Worcester, MA (ORH-Worcester Regional). Bradley International Airport is 46 miles away, with nearby hotels such as the 4-star DoubleTree by Hilton Hartford - Bradley Airport, located 1 mile from the airport. Albany International Airport is 35 miles away, offering options like The Landing Hotel at Rivers Casino & Resort, just 8 miles from the airport. Worcester Regional Airport is 72 miles away, with the 4-star Beechwood Hotel located 5 miles from the airport. Transportation services are readily available from these hotels to their respective airports.