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Vacation rentals in Pittsfield

Vacation rentals in Pittsfield

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pittsfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Spacious Duplex in Heart of the Berkshires
    SUPERHOSTEntire house · 4 guests · 2 beds · 1.5 baths
    Spacious Duplex in Heart of the Berkshires

    Equidistant to MASS MoCA, Tanglewood, Clark Art Institute, Jacob's Pillow, Jiminy Peak, and more, and walking distance to downtown Pittsfield. Spacious, two-floor duplex in the heart of the Berkshires.

    What guests are saying:

    “We had a great time in Jonathan's and Abby's place in Pittsfield. The duplex is very clean and nicely furnished. The kitchen is very well stocked with about everything you would need to cook meals just as you would at home. We enjoyed the proximity to lots of nature spots nearby, namely Cheshire Cobbles and Wahconah Falls.”

  • One Bedroom in Downtown
    Entire apartment · 2 guests · 0 beds · 1 bath
    One Bedroom in Downtown

    Stay steps from North Street in this beautiful, fully-furnished one-bedroom apartment. The apartment includes a Keurig coffeemaker and toaster, and comes fully stocked with dishes, cutlery, and pots and pans. High quality linens are provided, as well as two TV's with a Roku for streaming capability, and a wonderful Bose wireless speaker. Washer/dryer onsite. Parking available.

    What guests are saying:

    “Great location by many coffee shops, bars and restaurants. 4 minute drive to a supermarket. Having laundry was a major plus for me as I was there on a weekly long bike rides.”

  • Modern, Spacious Master Bedroom and Bathroom
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1.5 baths
    Modern, Spacious Master Bedroom and Bathroom

    Hi, I'm Isla, This Master bedroom is large and bright with a King sized bed, TV, desk and large bathroom with access to a backyard facing deck. You will have exclusive use of a spacious living room and dining area. The Townhouse is located in a cull de sac in a private community, so it is very quiet and safe. Includes a spacious, clean and bright kitchen fully stocked with pots, pans and utensils. Conveniently located close to everything the Berkshires has to offer.

    What guests are saying:

    “The setting is perfect and the quiet wooded views from the large windows and decks are lovely, from the sunlight on the foliage in the fall, to the clear starry skies and moonlight from your private deck. It is on a quiet wooded cul-de-sac. The rooms are clean and very spacious. The kitchen is great for cooking your own meals, and the sumptuous couch is a cozy place to sip your tea by the picture window. Isla is a warm and welcoming, charming and caring host, sincerely trying to make your stay with her be one of perfection. She eagerly welcomes suggestions for improvements, but not many are needed !!”

Vacation rentals for every style

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Popular amenities for Pittsfield vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Pittsfield

DESIGNERS COTTAGE CK SEPT OCT "SPECIALS"
Entire cottage
DESIGNERS COTTAGE CK SEPT OCT "SPECIALS"
Price:$185 / night
Cozy and Quiet in the Berkshires
SUPERHOSTPrivate room
Cozy and Quiet in the Berkshires
Price:$135 / night
Heart Of The Berkshires
SUPERHOSTEntire apartment
Heart Of The Berkshires
Price:$135 / night
Spacious and quiet central Berkshire home!
Entire house
Spacious and quiet central Berkshire home!
Price:$85 / night
Large guest suite w/private bath in the Berkshires
SUPERHOSTPrivate room
Large guest suite w/private bath in the Berkshires
Price:$90 / night
Safe Harbor in Private Cottage By The Woods
SUPERHOSTEntire cottage
Safe Harbor in Private Cottage By The Woods
Price:$202 / night
One private single room in Lenox
Private room
One private single room in Lenox
Price:$50 / night
Mi Casita Rm#1 (1 Queen Bed)
SUPERHOSTPrivate room
Mi Casita Rm#1 (1 Queen Bed)
Price:$78 / night
A farmhouse in an old mill town
SUPERHOSTPrivate room
A farmhouse in an old mill town
Price:$89 / night
Country Inn Suite at Jiminy Peak
Resort room
Country Inn Suite at Jiminy Peak
Price:$152 / night
Haddock Hill House
Private room
Haddock Hill House
Price:$144 / night
Mi Casita Rm#2 (1 King Bed or 2 Twin Beds)
SUPERHOSTPrivate room
Mi Casita Rm#2 (1 King Bed or 2 Twin Beds)
Price:$90 / night
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