Pittsfield Vacation Rentals

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Browse Select Pittsfield Vacation Homes

Our top choices for Pittsfield vacation homes

"Fantastic location for easy ski on ski off."

"Beautiful area and gorgeous leaves. Liked having a weber grill."

"Margarete and Alice welcomed us upon arrival. The house was the quintessential New England home! It was super clean, our bed was very comfortable with soft welcoming linens. The views are incredible, and the property provided much needed peace and tranquility. The weather was not the best but we managed to find plenty to do in the area. Alice, Margarete's black lab, took us for a hike on the property. She was an excellent playful guide! We look forward to returning to this peaceful retreat in...

"Excellent customer service and beautiful, well-maintained property."

CA $218 total

includes taxes & fees

Aug 24 - Aug 25

"It was a wonderful stay in a beautiful home close to all of the places we wanted to spend time!"

"Absolutely loved it!!! Amazing house. Will definitely stay again!"

"Nice rental for our family and the owner was very rsponsive."

"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"

"A true gem."

"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"

CA $262 total

includes taxes & fees

Aug 24 - Aug 25

"Condo was clean & well furnished. Only stayed one night after a visit to Quechee, Woodstock, and area."

CA $237 total

includes taxes & fees

Aug 24 - Aug 25

"Great place"

"We loved the community space and how the layout was conducive to comfort and space to gather together.Bonus to have so many bathrooms! The windows and light were spectacular!"

"Beautiful house on an amazing piece of property. The house was very comfortable for two families of four. It has everything you could need and more. The hosts were very responsive. We will definitely stay here again."

"Big and spacious. "

"The home was so comfortable and had a gorgeous view of the mountains. It was so convenient to the ski slopes. Our family of 4 really enjoyed our stay."

"Property owner was excellent! We enjoyed our stay."

"This rental was not only clean and roomy but in a great spot. It was spacious throughout and the beds were comfortable. The backyard and hot tub were very nice too.. I would definitely stay again!"