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Compare 471 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 12+
Here's the main living area - dining is up on the left
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (108)
"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the time we left. Thank you David! We are looking forward to next year."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (449)
"Wonderful cabin with every detail provided. We felt pampered and relaxed immediately. Perfect location for everything from hiking, swimming to skiing"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Recent reviews of Pittsfield hotels
Expedia verified reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

5/5 Excellent
"After staying in Boston for 2 nights, it was so nice to come to this quiet, welcoming hotel in the mountains of Vermont! The staff made us feel right at home when we checked in and seemed to really care. Our room was very clean and we enjoyed the restaurant and the game room. We could not have chosen a better place to stay! "
A verified traveler stayed at The Mountain Inn at Killington
Posted 1 day ago
The Mountain Inn at Killington