Vacation rentals in Pittsfield
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Top-rated vacation rentals in Pittsfield
Guests agree: these stays are highly rated for location, cleanliness, and more.
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.
“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!”
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!
“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!”
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.
“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.”
