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Compare 626 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
9.8 out of 10, Exceptional, (22)

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
10.0 out of 10, Exceptional, (2)

Cozy Private Bedroom with Own Entrance - No Shower
Cozy Private Bedroom with Own Entrance - No Shower
10.0 out of 10, Exceptional, (3)
The price is SAR 300
SAR 458 total
includes taxes & fees
16 Apr - 17 Apr

Spacious country home, beautiful sunsets, 40 acres
Spacious country home, beautiful sunsets, 40 acres
10.0 out of 10, Exceptional, (32)
The price is SAR 488
SAR 1,804 total
includes taxes & fees
16 Apr - 17 Apr

Classic Vermont Farmhouse near Sugarbush Resort
Classic Vermont Farmhouse near Sugarbush Resort
9.6 out of 10, Exceptional, (35)

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
9.2 out of 10, Wonderful, (36)

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
10.0 out of 10, Exceptional, (3)

The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
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.
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Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+
Killington area home - 4-seasons & hot tub. Sleeps 13+
9.8 out of 10, Exceptional, (117)

Private Killington Area Inn all to Yourself!
Private Killington Area Inn all to Yourself!
10.0 out of 10, Exceptional, (38)

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (489)
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
Recent reviews of Pittsfield hotels

The Shire Woodstock
5/5 Excellent
"The property is well maintained. Its staff is so friendly and helpful as well. We loved The River House with the beautiful terrace and rocking chairs overlooking the river. So peaceful. The amenities and sitting room were a lovely touch. "
A verified traveler stayed at The Shire Woodstock
Posted 2 days ago
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