Holiday houses in Pittsfield

Restored 1735 Granary I King Bed + Views & Pool

Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 15-ft vaulted ceilings, original wide-plank floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub + standing shower. Centrally located in the Berkshires and just minutes to Lenox and Tanglewood. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

NEW RENO - Chalet-style farm loft near Tanglewood

Welcome to Shaker Meadows, a historic 18th century Berkshires farm. This newly renovated chalet-style loft in the farm’s 1940s creamery has a full kitchen, & deck looking out onto the Berkshire mountains. Explore winding paths around 50 acres of farmland & hills or drive 10 mins to Hancock Shaker Village, 15 mins to Tanglewood/Jiminy Peak—a wonderful base for exploring the art, music, and history of the Berkshires. Great for couples, families, & solo adventurers. Kid- and pet-friendly.

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

The Carriage House: Spotless, Charming 2 Bedroom

The 1820 Carriage House is in the heart of the beautiful Berkshires. Williamstown and Mass MoCA are up the road, Lenox is to the south, and Mount Greylock is around the corner. It's a fully equipped 950 square foot cottage, light, airy, charming and immaculate, conveniently located in Lanesborough. With seven rooms, two stories, a comfy queen and full-sized bed, full kitchen, washer/dryer and off-street parking, your Berkshire visit will be as comfortable as it is memorable.

Comfortable Pittsfield Loft

Located in the center of the Berkshires, this newly renovated Pittsfield apartment is comfortable and convenient. Come enjoy the new kitchen and delightful walk in shower. Centrally located to all of the wonderful Berkshires attractions this one bedroom apartment offers new appliances, driveway parking, washer and dryer. Yuhong and Mike live on-site in the apartment below and they are dedicated to providing an excellent guest experience. THIS IS A NO SMOKING APARTMENT

Comfy Quaint Tavern

Experience this beautifully renovated unit which is available for overnight guests. Enjoy the charm of yesteryear and the echo of laughter and friendship. This property was originally a tavern that opened in 1933 and received one of the first liquor licenses in the area after prohibition was repealed. Now a fully renovated one bedroom unit (within two-unit property) with so much of the historic charm restored for your recreation and relaxation. Off street parking.

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with full bathroom. The spacious room features a high-end queen bed and a small table for dining and working, a small frig, microwave, toaster oven, and pour-over coffee in a nook outside the bedroom. Popcorn, oatmeal 1/2 and 1/2 are provided. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas.1 mile to Berkshire Medical Center. 20 minutes to Lenox. Fire Pit.

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

The Sunset House

Enjoy a getaway in the beautiful Berkshires! Our cozy home is on a quiet dead end street with a 3 minute walk to Pontoosic Lake. Centrally located, a 15 minute drive to Jiminy Peak Mountain Resort, 15 minutes to Bousquet Mountain Ski Area, a 25 minute drive to the famous Tanglewood or Naumkeag. The home is equipped with all basic needs, washer/dryer, smart TV's in living room and bedroom, WIFI included. 1 potty trained dog is welcome per stay.