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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.

Cozy Suite with huge bar and stone fireplace!
Entire apartment · 4 guests · 1 bed · 1 bath
Cozy Suite with huge bar and stone fireplace!

Visit Tanglewood, Kripalu, Jacobs Pillow, Jiminy Peak, Bousquet Mountain, Lebanon Valley Speedway, Albany, Pittsfield, Lenox... go for a hike, ski, visit Furnace Brook Winery or just relax on our property and unwind.

What guests are saying:

“My boyfriend and I had an amazing over-night stay at this home. The creek behind the house was so beautiful and had many perfectly flat skipping stones. The bar in the house was such a cool touch and a big reason why we chose to book this place. If you are looking for a fun rustic getaway with a friendly host, this is the place for you!”

Cozy Stockbridge Cottage
SUPERHOSTEntire cottage · 5 guests · 3 beds · 1 bath
Cozy Stockbridge Cottage

Small rustic Berkshire home, updated for comfortable year-round living. Located on same road as Tanglewood (3 miles), Kripalu (2 miles), Stockbridge Bowl (1 mile), Botanical Garden (1 mile). Less than 5-minute drive to historic downtown Stockbridge, Red Lion Inn, Norman Rockwell Museum, and all the four season activities of the Berkshires!

What guests are saying:

“We had a fantastic stay at Marks’ place - the cottage had all the amenities we needed! It’s still a work in progress but it’s rustic and homey with the wooden rafters. Perfect for a pre-Christmas weekend, they make sure to stock the home with plenty of blankets and space heaters which we appreciated for our stay. Full kitchen, tons of space, the electric fireplace was homey and it feels so private that you hardly realize you’re less than ten mins to town with all the shops and restaurants. We had cocktails at the Red Lion Inn, enjoyed the winter lights at Naumkeag, and loved seeing the Norman Rockwell museum. A perfect snowy weekend in small town Massachusetts!”

CovidClean/Tanglewood/Private Ranch/Views/Pets/Ski
SUPERHOSTEntire guest suite · 5 guests · 2 beds · 1 bath
CovidClean/Tanglewood/Private Ranch/Views/Pets/Ski

Pet Friendly Winter Getaway!Modern suite with full kitchen on private horse ranch.Wake to horses in the fields,hiking trails and breakfast on your patio. Perfect for individuals, couples or families. Adventure seekers, artists, animal lovers, Yogis, hikers, writers and couch potatoes will equally love the location. Near all ski areas(Jiminy Peak/ Catamount/Bousquet/Butternut),museums(Norman Rockwell/Mass MoCA), shopping, Tanglewood,Jacobs Pillow, Kripalu,Canyon Ranch. Horse activities available.

What guests are saying:

“Hayley's place is a sweet, clean sanctuary. The place is slightly on a hill, and you will have the landscape (snow, if it is winter) and her gorgeous horses in view. Her horses galloped right up to us, once they spotted us walking by. Friendly, stunning horses. The setup with the two bedrooms, common space, bathroom and kitchen were spotless, and all was as expected according to the listing. Our family of four (husband, myself, 4 year old and an infant) remained toasty and comfortable during our wintry stay. Hayley was attentive to our unique needs (car rental could not make it exactly to the home, and she shuttled us to and from our car!) and she was the generous host - lending us her snow boots, providing bottles of water and hot tea upon arrival. She treated us amid the challenges we had faced. Our 4 year old enjoyed riding a horse and feeding the donkeys. Really made our trip and we could not have been happier with our stay at Hayley's ranch.”

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

Charming Housatonic Village Cape
SUPERHOSTEntire house
Charming Housatonic Village Cape
Price:$233 / night
Marie's Place
SUPERHOSTEntire apartment
Marie's Place
Price:$100 / night
Cute Cozy Comfy Cottage in the Berkshires
SUPERHOSTEntire cottage
Cute Cozy Comfy Cottage in the Berkshires
Price:$132 / night
Furnished Condo at Jiminy Peak (For Sale)
SUPERHOSTEntire condominium
Furnished Condo at Jiminy Peak (For Sale)
Price:$173 / night
Modern,Comfortable, Classic House-Downtown Lenox
SUPERHOSTEntire house
Modern,Comfortable, Classic House-Downtown Lenox
Price:$399 / night
Sharon's Place 4 ..... pets, and 420 friendly!!!!
SUPERHOSTEntire apartment
Sharon's Place 4 ..... pets, and 420 friendly!!!!
Price:$45 / night
1/2 mile from Red Lion Inn.  Historic Stockbridge.
SUPERHOSTEntire house
1/2 mile from Red Lion Inn. Historic Stockbridge.
Price:$626 / night
Honeysuckle Rose Cottage
Entire house
Honeysuckle Rose Cottage
Price:$97 / night
The Sail Loft
SUPERHOSTEntire cottage
The Sail Loft
Price:$87 / night
HawksNest: quiet 2BR apt, heart of the Berkshires
SUPERHOSTEntire apartment
HawksNest: quiet 2BR apt, heart of the Berkshires
Price:$75 / night
Berkshire Guest Suite
SUPERHOSTEntire guest suite
Berkshire Guest Suite
Price:$67 / night
Riverfront Getaway
SUPERHOSTEntire house
Riverfront Getaway
Price:$155 / night
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