Compare Vacation Rentals & Airbnb in Pittsfield, MA

This secluded three-bedroom lodge, formerly owned by BSO timpanist Vic Firth, is situated beside a brook on a private quarry pond in Lenox, offering convenient access to Tanglewood (1.4 km), The Mount (1.4 km), and Shakespeare & Company (1.6 km).
This family-friendly and pet-friendly accommodation for six guests features air conditioning, high-speed Wi-Fi, a modern kitchen with a fridge, microwave oven, and dishwasher, and a spacious garden with an outdoor grill, with Bousquet Mountain Ski Area (1 km) and Kennedy Park (1 km) nearby for outdoor activities.

This waterfront holiday home in Pittsfield offers direct access to Onota Lake, located a short distance from the Tanglewood Music Centre and the Crane Museum of Papermaking, with the Colonial Theatre and Herman Melville's Arrowhead also nearby.
This spacious 167 square meter residence accommodates up to 10 guests across 3 bedrooms and 2 bathrooms, featuring a large dock, expansive outdoor living space with a covered deck and sunroom, and modern climate control, ideal for water sports, cultural excursions, and nearby outdoor pursuits.

This charming 3-bedroom house is located on a quiet street in southeast Pittsfield, just a short drive from local restaurants, shops, and popular attractions like Hancock Shaker Village and MASS MoCA. The home has received excellent ratings for location, cleanliness, and overall experience.
The house offers a spacious living area with a comfortable gas stove and new furniture, perfect for relaxing after a day of exploring. Guests can enjoy the home's amenities, including a fully equipped kitchen, air conditioning, a large garden, and ample off-street parking.

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.

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 apartment in Pittsfield is located just 2 kilometres from the town centre and 3 kilometres from the lake, offering easy access to both the vibrant town and the tranquil lakeside. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The property offers a spacious living space suitable for up to 5 guests. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, a private garden, off-street parking, and a washer and dryer.

This three-bedroom, two-bathroom apartment in Friendly Hills, Hancock, offers stunning panoramic views and direct access to private hiking trails, with Hancock Shaker Village nearby.
The mid-century modern flat, sleeping six, boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, Wi-Fi, parking, and unique design features inspired by Frank Lloyd Wright.

This three-bedroom Pittsfield lakeside house, boasting excellent guest reviews, offers direct access to Onota Lake with a private dock and is conveniently located near Pittsfield's ski slopes and hiking trails, the precise distance unspecified.
Sleeping up to five guests, this self-catering property features a fully equipped kitchen, a large deck with mountain views, a fenced yard, on-site laundry, and access to kayaks and paddleboards; a BBQ area is also available in the shared backyard.

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 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 rustic cottage in Lenox offers a serene woodland setting beside a brook on a private quarry pond, with Tanglewood and Bousquet Mountain Ski Area a mere 6-9 minute drive away.
This 76 square meter property accommodates up to six guests with three bedrooms, a fully-equipped modern kitchen, high-speed Wi-Fi, and a garden with an outdoor grill, making it an ideal Berkshire retreat for families and pet owners.

This detached house is situated in a rural area near Richmond, 11.6 kilometres from the Tanglewood Musical Center and 17.7 kilometres from the Norman Rockwell Museum.
This property offers accommodation for up to 11 guests across 3 bedrooms and 2 bathrooms, featuring a 256 square metre floor area, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a hot tub, a terrace, a garden, and on-site parking.

This two-bedroom flat in Southeast Pittsfield provides a quiet base, conveniently located for accessing Berkshire attractions such as the Clark Art Institute and Tanglewood, as well as skiing and hiking opportunities within a 30 kilometre radius.
The accommodation offers a fully equipped kitchen, a king-sized bed and a queen-sized bed, a large bathroom with a walk-in shower, a separate half-bathroom with a washer and dryer, and Smart TVs throughout, comfortably accommodating up to four guests with keyless entry.

This one-bedroom flat in Pittsfield is conveniently located for exploring local culture and history, with Tanglewood Music Center and Colonial Theater just a short distance away, and Herman Melville's Arrowhead and Hancock Shaker Village also nearby.
This apartment offers accommodation for up to four guests, featuring a king-size bed, a sofa bed in the living room, air conditioning, and complimentary Wi-Fi, and is within easy reach of the Berkshire Museum and Bousquet Ski Area.

This five-bedroom holiday home is situated just a short distance from Pittsfield town centre, offering easy access to restaurants, shops and cultural attractions, and is only 11 kilometres from Tanglewood. The pet-friendly property features a fully equipped kitchen, a fireplace, a soaker tub, a covered porch, a barbecue and a garden, making it ideal for families or groups of up to nine people.

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.