Places to stay in Pittsfield, MA

This lakefront property on Onota Lake in the Berkshires offers stunning 180-degree views and is a short distance from Pittsfield's cultural attractions.
The one-bedroom, one-bathroom cottage sleeps four, features a fully equipped kitchen, air conditioning, a private beach, and direct lake access, making it ideal for families seeking a relaxing getaway near Pittsfield.

This charming house is situated in the Berkshires, just 30km from attractions like Tanglewood, The Mount, and MassMoca, offering a peaceful retreat in a picturesque setting. The house is ideal for families and groups of friends, with three bedrooms and two bathrooms, accommodating up to seven guests.
The house features a modern open-plan layout with a fully equipped kitchen, a garden, and a wrap-around deck with stunning views of the surrounding lake and mountains. Guests can enjoy al fresco dining, relax in the spacious living area, or explore the nearby hiking trails and state forests.

This family-friendly apartment in Pittsfield is located just 1.6 kilometres from the Ashuwillticook Rail Trail and 12.8 kilometres from Pittsfield State Forest, offering convenient access to outdoor pursuits and winter sports at Bousquet Mountain Ski Area (12.8 km) and Jiminy Peak Mountain Resort (19.2 km), with Park Square and the Berkshire Museum approximately 6.4 kilometres away.
This spacious accommodation sleeps up to 10 guests across 3 bedrooms and 3 bathrooms, featuring a full kitchen with two ovens and a Crockpot, air conditioning, a fireplace, a deck, balcony, gazebo, and a main-level bedroom and bathroom for accessibility, alongside family amenities like a high chair and Pack 'n Play for a comfortable stay.

This lakeside dwelling is situated just a 20-minute drive from Jiminy Peak Ski Resort, Tanglewood, and the Berkshire Museum, offering easy access to the region's attractions. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The spacious apartment boasts four bedrooms, four bathrooms, and an additional sleeping area, comfortably accommodating up to 10 guests. Enjoy the lakefront location with direct access to the water, a dock, kayaks, a fire pit, multiple decks, a garden, and a jacuzzi.

This 460 square meter residence in Pittsfield is situated a 11-minute walk from the Housatonic River and a 14-minute walk from the Colonial Theatre.
This family-friendly holiday home accommodates up to 10 guests across 5 bedrooms and 4 bathrooms, featuring a heated swimming pool, garden, on-site parking, and a fully equipped kitchen.

This charming cottage is located on the Pittsfield/Lenox border, just a few kilometres from Tanglewood and within easy reach of Pittsfield's restaurants, skiing, and autumn foliage attractions. It has received excellent ratings for its cleanliness, location, and user experience.
The cottage has one bedroom and one bathroom, accommodating up to four guests. It features original hardwood floors, a fireplace, high-end appliances, a king-size bed, luxurious linens, and access to a swimming pool, tennis court, and nature trails.

This Lenox holiday home is situated in a rural setting, less than 3km from the Housatonic River and the historical Arrowhead, home of Herman Melville.
This four-bedroom, three-bathroom property boasts 281 square metres of living space, a private pool, barbecue facilities, and sleeps eight guests, offering free Wi-Fi and a fully equipped kitchen.

Berkshire Mountain Lodge is conveniently located in Pittsfield, just a short drive from popular attractions like Berkshire Museum, Barrington Stage Company, and Tanglewood. This property has received very good user ratings and excellent location ratings, making it a popular choice for travellers.
This lodge offers a comfortable one-bedroom, one-bathroom accommodation with a full kitchen, a sofa bed for extra guests, and a private bathroom with hairdryer and free toiletries. Enjoy a range of amenities including an indoor swimming pool, a fitness centre, a hot tub, a games room, free Wi-Fi, and a restaurant and bar on-site.

This two-bedroom apartment is conveniently located in Pittsfield, just 10 kilometres from Bousquet Ski Resort and 15 kilometres from Jiminy Peak. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is suitable for up to four guests and features a spacious living and dining area, a well-equipped kitchen, a screened-in porch, and a shared backyard. Guests can enjoy amenities such as air conditioning, internet access, a washing machine and dryer, and a modern bathroom with a double vanity.

This two-bedroom flat is located in a quiet neighbourhood in Pittsfield, just 5km from Bousquet Ski Area and a short drive from Jimmy Peak, Tanglewood, Mass MoCA, and a variety of restaurants. This property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The flat offers ample space for relaxation and privacy, comfortably accommodating up to four guests. Guests can enjoy a fully equipped kitchen, air conditioning, parking, and internet access, as well as the convenience of being close to hiking and biking trails, making it an ideal base for exploring the Berkshires.

This Berkshires detached house in Pittsfield is a short drive from Cranwell Spa & Golf Club (15.9 kilometres), Tanglewood (17.7 kilometres), and the Norman Rockwell Museum (25.7 kilometres), with Albany International Airport located 72.4 kilometres away.
This spacious three-bedroom, two-bathroom property offers 143 square metres of living space, accommodating up to 11 guests with amenities including air conditioning, a dishwasher, microwave, on-site fitness centre, and private parking.

This Lanesborough lakeside house boasts a prime location on Pontoosuc Lake, offering 120 ft of private shoreline and easy access (within 32km) to Mount Greylock and Tanglewood.
The 2600 sq ft property features three bedrooms, two bathrooms, sleeping up to eight guests, and includes a private dock, gas fireplace, Weber grill, Roku TVs, and proximity to local attractions such as miniature golf and Krispy Kreme.

This flat in Pittsfield is located in a central, walkable neighbourhood, offering easy access to museums, music venues, theatres, lakes, rivers, and trails, with day trips to Great Barrington and Lenox, Massachusetts, within 16 kilometres, and Hudson and Chatham, New York, within 48 to 96 kilometres.
This accommodation for three guests includes a kitchen with a fridge, freezer, and microwave, air conditioning, a garden with a firepit, outdoor dining facilities, a grill, and a large, fenced backyard, alongside access to a fitness centre and parking, with pets welcome.

This newly built Lanesborough residence is situated on a quiet street, a mere 300 metres from Pontoosuc Lake, and a short drive to Jiminy Peak for skiing, the Ashuwillticook Rail Trail for cycling, and Pittsfield State Park for its natural beauty.
This spacious three-bedroom, three-bathroom house accommodates up to eight guests and includes amenities such as air conditioning, Wi-Fi, a kitchen, and parking for four vehicles, with outdoor EV charging available.

This Pittsfield lakeside property offers stunning lake views and easy access to Berkshire attractions such as Tanglewood and Mass MoCA, with distances varying depending on the precise location within the Berkshires.
This two-bedroom, one-bathroom holiday home sleeps four guests and boasts a fully equipped kitchen, Jacuzzi, fitness centre, garden, and patio with a fire pit; a hot tub is available for an additional fee.

This apartment is located in a great neighbourhood in Pittsfield, just a short distance from the river and a canoe launch. It has consistently received excellent ratings for cleanliness, location and user experience.
This charming three-bedroom property can accommodate up to six guests and offers a fully equipped kitchen, washer and dryer, a garage and storage space. Enjoy the convenience of a garden, air conditioning and internet access, as well as the unique charm of colonial lighting and tasteful design.