Places to stay in Pittsfield, MA

This Lanesborough lakeside property, near Pontoosuc Lake, is conveniently located 3.2km from Balanced Rock State Park, 8km from Pittsfield State Forest, and 12.9km from Jiminy Peak Mountain Resort.
This five-bedroom, two-bathroom holiday home offers 186 square metres of space, accommodating up to six guests, and boasts direct waterfront access with kayaks, canoes, a pedal boat, a private dock, a furnished sunroom, a fire pit, a gas grill, and parking for seven vehicles plus small trailers or boats.

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.

This apartment is conveniently located in downtown Pittsfield, just 7km from the Bosquet ski area and 28km from Jiminy Peak, making it ideal for exploring the town and enjoying winter sports. The property has received excellent ratings for cleanliness, location, and user experience.
The apartment has three bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and a wet towel basket in each bedroom, ensuring a comfortable stay.

Hygge House is situated in the Berkshires, a central region of Massachusetts, 24 kilometres from Mount Greylock State Reservation and 14.5 kilometres from Mass Audubon's Pleasant Valley Wildlife Sanctuary. This property has received excellent ratings for its location, cleanliness, and overall user experience.
This three-bedroom, two-bathroom home spans 195 square metres and comfortably accommodates up to six guests. The house offers a range of amenities, including private water access, two nearby beaches, fishing opportunities, hiking trails, a fireplace, multiple living areas, a well-equipped kitchen, a children's play area, a yoga/meditation space, and the option to arrange in-home massage services and meals prepared by local chefs.

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 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 Pittsfield holiday home, a short drive (under 5km) from Hancock Shaker Village and 3 minutes from Balderdash Cellars, offers convenient access to local attractions.
The three-bedroom, two-bathroom apartment includes an attached garage, in-unit laundry, Wi-Fi, a fully equipped kitchen with oven, stovetop, refrigerator, microwave, coffee maker and toaster, and air conditioning; sleeps up to six guests comfortably.

This two-bedroom flat in Richmond offers a country cottage ambiance with a private community beach on Richmond Pond, situated a short walk from Tanglewood and Bousquet ski area.
This pet-friendly accommodation for four features a wood-burning fireplace, a back balcony with woodland views, and a newly renovated kitchen, with access to a tandem kayak for use on Richmond Pond.

This six-bedroom, four-bathroom holiday home in Pittsfield is located a 0.8km walk from the Canoe Meadows Wildlife Sanctuary and a 3.2km drive from the Housatonic River.
The property sleeps fourteen guests and features a fully equipped kitchen with dishwasher and microwave, in-unit laundry, air conditioning, on-site parking, and outdoor barbecue and fireplace facilities; nearby attractions include the Berkshire Museum, Bousquet Ski Area, and the Berkshire Scenic Railway Museum.

This Richmond flat offers a serene setting by Richmond Pond, just 300 metres from Balderdash Cellars and 8 kilometres from Tanglewood.
This spacious 255 square metre split-level property accommodates up to six guests and includes a newly renovated kitchen, air conditioning, a jacuzzi, a terrace, a garden, parking, and two kayaks and bicycles for exploring the area.

This renovated two-bedroom apartment in Pittsfield, Massachusetts, is conveniently located near Highway 7, offering easy access to cultural attractions such as the Kripalu Center for Yoga & Health, Lenox, and Tanglewood (all within a 24km radius).
The property features a spacious layout, accommodating up to four guests, with a kitchenette, full bathroom, and a screened-in porch; shared access to a garden is also available.

This lakefront cottage in the Berkshires offers direct access to the water, with the Ashuwilltook Rail Trail 8 kilometres away and Barrington Stage Company 8 kilometres distant.
This recently renovated two-bedroom dwelling sleeps up to eight guests, featuring a fully equipped kitchen, a grill, a large deck, and a firepit, with nearby attractions including Ramblewild Adventure Park and Bousquet Mountain, and year-round activities from swimming to skiing.

This southern Pittsfield holiday home, minutes from both Pittsfield and Lenox town centres, provides easy access to Berkshire attractions such as Tanglewood (approximately 16km away).
The four-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen, private garden with deck and BBQ, a dedicated cinema room, and a games room with foosball and Pac-Man; nearby activities include the Barrington Stage Company and Bousquet Ski Area.

This seven-bedroom Pittsfield holiday home is conveniently located within a 1.6km walk of the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, and under 1.6km from the Housatonic River and Barrington Stage Company.
This spacious 307 square metre property sleeps nine guests and boasts a fully equipped kitchen, two bathrooms, laundry facilities, a fireplace, terrace, garden, and parking, all within easy reach of Pittsfield's cultural attractions and transport links.