Best apartment offers in Pittsfield, MA

This five-bedroom, three-bathroom house is situated in the exclusive Black Diamond section of Jiminy Peak Mountain Resort in the Berkshires, offering ski-in/ski-out access to Grouse Run.
The 2600+ sq ft property boasts a spacious layout including a large great room with fireplace, game room, chef's kitchen, and private ski room with drying facilities; sleeping up to ten guests and providing access to the resort's pool, hot tubs, and fitness centre.

This expansive holiday home is situated in a secluded, wooded setting near New Lebanon, approximately 16 kilometres from Pittsfield's extensive retail and service amenities.
This pet-friendly residence offers seven bedrooms and four bathrooms for up to ten guests, featuring a fully equipped kitchen, air conditioning, a swimming pool, fitness centre, and ample parking, with extensive grounds ideal for outdoor activities and family gatherings.

Polly's Place, a four-bedroom Lanesborough holiday home, is situated near the summit of a hill, approximately 1.6km from the Ashuwillticook Rail Trail, 1.3km from Elle Day Spa, and 5.6km from the Mount Greylock Visitor Centre.
This self-catering property sleeps six guests and boasts a 1960s Tappan range, a sunken sunroom with fireplace, modern amenities including smart TVs and Bose speakers, plus a large garden perfect for outdoor games; it's even been a favourite retreat for Olympic skier Mikaela Shiffrin.

This comfortable home is located in a central Pittsfield neighbourhood, just a short distance from attractions such as Tanglewood, the Norman Rockwell Museum, and Mass MOCA. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It is equipped with a fully equipped kitchen, air conditioning, a garden, and a fitness centre, providing everything you need for a relaxing and enjoyable stay.

This ground-floor apartment at Jiminy Peak Mountain Resort in Hancock, Massachusetts offers ski-in/ski-out access in winter and proximity to summer activities.
The one-bedroom, one-bathroom flat sleeps four guests, featuring a king bed, queen sofa bed, fully equipped kitchenette with appliances including a dishwasher and air fryer, plus a private coded lock, smart TVs, and access to resort amenities such as a heated pool and fitness centre.

This apartment is located in the Berkshires, a short drive from Pittsfield, just 5 km from Bousquet Ski Mountain and 20 km from Jiminy Peak, making it a great choice for those looking to explore the region's natural beauty and outdoor activities. It has received excellent ratings for location, cleanliness, and overall experience.
This single-storey property can accommodate up to 5 guests and offers a comfortable and private stay. It includes a fully equipped kitchen, a garden, a deck and an enclosed porch, as well as access to a grill and yard games, perfect for relaxing and enjoying the outdoors.

This three-level condominium in Jiminy Peak's Mountainside district offers convenient walking access to the ski lifts and village, situated within Hancock.
This designer-appointed apartment sleeps eight, featuring three bedrooms including two king suites, four bathrooms, a well-equipped kitchen with a microwave and dishwasher, and parking, with the Jiminy Peak adventure park and Mount Greylock State Reservation nearby.

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 Richmond flat offers a secluded Berkshire escape on 2.5 acres, located a short drive from Balderdash Cellars (1.6 kilometres), Hancock Shaker Village (6.4 kilometres), Bousquet Mountain Ski Area (14.5 kilometres), Tanglewood (22.5 kilometres), and the Norman Rockwell Museum (27.4 kilometres).
This 191 square metre residence accommodates up to six guests with three bedrooms and two bathrooms, featuring a fully equipped kitchen, an outdoor grill, high-speed Wi-Fi, and a garden, with pets welcome for a one-time fee.

This three-bedroom house is situated on a lake in Lanesborough, Massachusetts, just 9.6 kilometres from Mount Greylock State Reservation, offering stunning lake views and proximity to the highest peak in Massachusetts.
The property features a Jacuzzi, a terrace, a garden, and parking, and can accommodate up to six guests, making it ideal for families or groups of friends looking for a relaxing getaway.

This one-bedroom flat in Pittsfield is located in the scenic Berkshires, offering a mountain lodge retreat ideal for exploring the region's ski resorts, fall foliage, and summer outdoor activities.
This apartment accommodates up to four guests and features internet, air conditioning, a kitchen, a swimming pool, a Jacuzzi, a fitness centre, and parking.

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.

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 Lanesborough lakefront property offers spectacular sunrise views and private dock access, located a short drive from Tanglewood and several art museums.
The four-bedroom, two-bathroom house sleeps seven guests and boasts a fully equipped kitchen, jacuzzi, garden, parking, and excellent guest ratings; nearby activities include hiking in state parks and skiing at various resorts.

This four-bedroom apartment in Pittsfield is located just 1.6 kilometres from Bousquet Ski Area and within walking distance of Guido's Marketplace, a popular local grocery store. The apartment has four bathrooms, a fully equipped kitchen, a washing machine, a fireplace, a Smart TV with a DVD player, a terrace, and access to a fitness centre and swimming pool.

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.