Find hotels in Pittsfield, MA from $80

Top reasons to visit Pittsfield

• Winter Sports Paradise: Pittsfield is a top destination for skiing and adventure enthusiasts, offering local ski resorts and picturesque slopes.
• Scenic State Parks: Explore beautiful state parks and serene lakes, perfect for outdoor activities and relaxation.
• Charming Downtown: Discover a blend of historical sites and modern attractions in the vibrant downtown area.
• Local Culture: Immerse yourself in the warm atmosphere and friendly locals that define New England charm.
• Diverse Accommodations: Enjoy a variety of lodging options, from cozy bed & breakfasts to luxurious hotels.

Find great hotels in Pittsfield

Discover the charm of Pittsfield, Massachusetts, where a diverse selection of hotels awaits to suit every traveler's needs. From budget-friendly options to luxurious stays, you'll find accommodations ranging from cozy bed & breakfasts to well-appointed hotels. Whether you're seeking pet-friendly amenities, adventure activities, or business facilities, Pittsfield has you covered. Experience the perfect getaway in this picturesque city with comfortable lodging options that cater to all types of visitors.

• The Yankee, Trademark Collection by Wyndham: Experience a business-oriented escape at The Yankee, Trademark Collection by Wyndham, located just 3 miles from Pittsfield. This hotel is tailored for the modern traveler, offering extensive business amenities including a 24-hour business center, multiple meeting rooms, and conference space. The sleek design and comfortable accommodations provide an ideal environment for productivity and relaxation. Whether you're traveling for work or looking to combine business with leisure, The Yankee ensures all your professional needs are met.
• The Black Swan Lee - Lenox, Ascend Hotel Collection: Discover a family-friendly adventure at The Black Swan Lee - Lenox, Ascend Hotel Collection, situated 9 miles from Pittsfield. Perfect for families and outdoor enthusiasts, this 3-star hotel boasts a variety of recreational activities, including skiing, fishing, and mountain climbing—all nearby. The property is pet-friendly, welcoming dogs with specific restrictions, making it a great choice for travelers with furry companions. Families will appreciate the amenities designed for children, including cribs and safety features, ensuring a comfortable stay for all ages.
• Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel: Nestled 12 miles from Pittsfield, the Holiday Inn Club Vacations Oak n’ Spruce Resort offers a delightful blend of adventure and comfort. This 3.5-star hotel is an excellent choice for families and ski lovers, with easy access to ski rentals and lessons, as well as snow tubing and snowboarding. On-site amenities include a mini-golf course, playground, and arcade game room, providing endless fun for children. The resort is designed to cater to the adventurous spirit while ensuring a memorable family getaway.

Discover the best areas to stay in Pittsfield

Pittsfield, Massachusetts, is a perfect destination for skiing, adventure, and sports enthusiasts. Explore the charming downtown area, where you'll find a blend of historical sites and modern attractions. Venture into the scenic beauty of Western Massachusetts, offering family-friendly activities and romantic spots for relaxation. Experience the warmth of friendly locals and immerse yourself in the vibrant New England atmosphere during your stay. Whether you're seeking adventure or tranquility, Pittsfield has something for everyone.

• Lenox: Located 7 miles from Pittsfield, Lenox is a charming town that attracts visitors year-round, especially during the summer months from June to August. Known for its romantic atmosphere and family-friendly activities, Lenox offers a vibrant entertainment scene with music concerts and theater performances. Outdoor enthusiasts will enjoy the nearby lakes, mountains, and parks, perfect for hiking, picnicking, or simply soaking in nature's beauty. Whether you're looking for a cozy getaway or an adventure-filled vacation, Lenox provides a delightful experience for all travelers.
• Williamstown: Situated 18 miles from Pittsfield, Williamstown is a picturesque town that thrives on adventure and sports, drawing visitors throughout the year. While peak tourist seasons occur in April and from June to July, Williamstown maintains a steady flow of travelers. This area is renowned for its skiing opportunities, with several ski fields and resorts catering to all skill levels. Explore the historic college campus nearby, or enjoy the stunning mountain and lake views that make Williamstown a breathtaking destination for those seeking both recreation and culture.
• Stockbridge: Just 12 miles from Pittsfield, Stockbridge is a cultural gem that welcomes visitors with open arms, especially from July to September. This charming town is rich in history and entertainment, featuring local theaters and music concerts that cater to diverse tastes. Visitors can explore the serene lakes, captivating monuments, and spiritual shrines that dot the landscape, making it a perfect spot for romantic getaways or cultural excursions. With its blend of artistic flair and natural beauty, Stockbridge offers a unique experience that captivates every traveler.

Things to do in Pittsfield

Pittsfield offers a fantastic vacation experience for ski and adventure enthusiasts, featuring popular activities like skiing at local ski resorts and exploring picturesque ski fields. In addition to winter sports, visitors can enjoy various area attractions that highlight the charm of this Massachusetts city, making it an ideal destination for sports lovers and outdoor adventurers alike.

Food and drinks

Pittsfield offers a delightful culinary scene! Try the Lobster Roll at The Roasted Garlic, or enjoy Mediterranean flavors at Papa Joe's Ristorante & Pizzeria. For a unique experience, visit Furnace Brook Winery at Hilltop Orchards for wine and entertainment, just 8 miles from downtown.

Shopping

Pittsfield offers great shopping options like Guido's Marketplace, a vibrant public market right in town. If you're up for a drive, visit Lee Premium Outlets, 11 miles away, for a variety of brand-name deals, or check out the Berkshire Mountain Country Store, located 10 miles from Pittsfield.

Recreation

Explore Kennedy Park for serene walks and nature trails, perfect for relaxation and mindfulness. At Wyndhurst Golf & Club, enjoy a round of golf surrounded by beautiful landscapes. Experience the magic of dance at Jacob's Pillow, where captivating performances ignite romance and cultural appreciation.

Adventure

At Jiminy Peak Mountain Resort, located 8 miles from Pittsfield, experience thrilling skiing and snowboarding on diverse trails. The nearby Skyline Trail, 13 miles away, offers breathtaking views and invigorating hikes through stunning landscapes. Bousquet Ski Area, within Pittsfield, provides a fun-filled atmosphere for ski enthusiasts.

Nightlife

Pittsfield offers a vibrant nightlife with the Colonial Theater showcasing captivating performances and romantic atmospheres. For a stellar experience, visit the nearby Hopkins Observatory for family-friendly entertainment. Don't miss Shakespeare and Company, where culture and creativity come alive just minutes away from downtown.

Booking tips and Expedia advantages for Pittsfield

To save money on your trip to Pittsfield, Massachusetts, consider visiting popular free attractions like the National Shrine of the Divine Mercy and Lee Premium Outlets. Travel during the cheaper months of March and November to December for lower accommodation rates. Book your hotel about a month in advance or look for last-minute deals on Expedia. Utilize their search tool to filter based on budget and preferences, and consider combining your hotel, flights, and activities for additional savings. Joining Expedia's One Key membership can also grant you exclusive discounts and OneKeyCash for future stays.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Pittsfield are March and November to December, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
• The best time to book a hotel: The cheapest time to book a hotel in Pittsfield is usually 1 month out from when you are planning to stay. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your choices based on your budget, desired location, and preferred hotel type. For instance, selecting the "Eco-certified" option will showcase sustainable and eco-friendly hotels that are currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel booking in Pittsfield with your flights and activities through an Expedia package.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in Pittsfield

Pittsfield, Massachusetts, is an ideal destination for skiing, adventure, and sports vacations. Visitors can explore beautiful state parks, serene lakes, and historic houses that offer a mix of outdoor activities and cultural experiences. Don't miss the nearby Great Barrington for additional attractions, and take time to discover the various districts within Pittsfield for a true taste of local charm and adventure.

• Hancock Shaker Village: Experience the rich history and culture of the Shaker community in this beautifully preserved village. Explore restored buildings, gardens, and interactive exhibits that showcase the Shakers' unique lifestyle and craftsmanship.
• October Mountain State Forest: Just 9 miles from Pittsfield, this expansive state forest offers endless outdoor adventures. Hike, bike, or picnic amidst stunning scenery, with trails that wind through lush forests and around serene lakes.
• Berkshire Museum: Located in Pittsfield, this family-friendly museum features a blend of art, history, and natural science exhibits. Enjoy interactive displays, live animals, and special events that cater to visitors of all ages.

Best time to go to Pittsfield

Visitor numbers in Pittsfield is generally unchanged in popularity throughout the year. The best time to visit Pittsfield is dependant 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	Average
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	Slightly Low

The nearest major airports for your trip to Pittsfield

Traveling to Pittsfield, Massachusetts, is convenient with several nearby airports. Albany International Airport (ALB) is 35 miles away, with hotel options like Park Manor Hotel and DoubleTree by Hilton Schenectady Downtown, both 8 miles from the airport. Bradley International Airport (BDL) in Hartford, CT, is located 46 miles from Pittsfield, offering nearby accommodations such as DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile away. Lastly, Pittsfield Municipal Airport (PSF) is only 3 miles from the city, with options like The Central Downtown Inn & Suites, 2 miles away, providing easy access for travelers looking to explore the region.