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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 AED 294
AED 448 total
includes taxes & fees
3 May - 4 May

Spacious country home, beautiful sunsets, 40 acres
Spacious country home, beautiful sunsets, 40 acres
10.0 out of 10, Exceptional, (32)
The price is AED 496
AED 1,785 total
includes taxes & fees
29 Apr - 30 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
The price is AED 1,010
AED 2,229 total
includes taxes & fees
27 Apr - 28 Apr
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)

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
9.0 out of 10, Wonderful, (42)
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 Jackson
5/5 Excellent
"The innkeeper, Lea, was excellent! She helped with our check in process. It went seamlessly. And she helped us when we had an issue with our TV. She was also extremely helpful with our breakfast and checkout! I would give her 5 stars! And the home was beautiful!!!"
A verified traveler stayed at The Jackson
Posted 2 days ago
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