Search Vacation Homes in Pittsfield

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Vacation Homes in Pittsfield

"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...

SAR 351 total

includes taxes & fees

14 Oct - 15 Oct

"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...

"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "

SAR 1,827 total

includes taxes & fees

3 Nov - 4 Nov

"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "

SAR 1,613 total

includes taxes & fees

14 Oct - 15 Oct

"Clean and comfortable home. Plenty of space for our family! Great quiet neighborhood made it easy to relax on our trip."

SAR 1,985 total

includes taxes & fees

21 Oct - 22 Oct

"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."

SAR 2,050 total

includes taxes & fees

3 Nov - 4 Nov

"Great spot in the Mad River Valley. Great host and close to lots!"

"A very comfortable stay for a family of four. Close to everything, clean, well stocked for breakfast making, and just enough room for everyone. We really enjoyed the fireplace after a day of skiing.Not sure why the heat setting turned to low 60s every night, but our blankets were warm."

"Awsome place to stay for a week! "

SAR 2,134 total

includes taxes & fees

17 Oct - 18 Oct

"Our group was in town for an archery event nearby and the location was perfect. Its peaceful and quiet but close to everything. It is an older house but well taken care of. Would definitely recommend. "

SAR 1,715 total

includes taxes & fees

14 Oct - 15 Oct

"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "

"Good area"

"Cool old farm house with an old fashioned set-up. Good value for the money considering how many people the house sleeps. Bathrooms are updated, kitchen is from the 80s. Furniture is outdated and ready to be replaced. Beds were very soft, not supportive. "

"Charming older home, clearly well loved. Enjoyed eating on the back porch, the generous living room space, and the sinks in every bedroom!"

"This was our second time staying at the house. Fantastic house for a long weekend skiing at Killington. Plenty of room for the adults and teens to unwind after a day on the slopes! Will definitely visit again. "

"Absolutely beautiful location, this "barndominium" has gorgeous mountain views, pond, firepit, a fenced in area for your pet (if needed), and a friendly goat! Wendy was a great host, immediately responded to questions, and has this place thoughtfully stocked. Only fifteen minutes to Middlebury. Highly recommended!!"

SAR 739 total

includes taxes & fees

27 Oct - 28 Oct