A lake surrounded by autumn-colored trees and a rocky shoreline.

Pittsfield house rentals

We found 319 house rentals — enter your dates for availability

Explore Pittsfield house rentals

Image of Beautiful Killington VT Ski & Mountain Bike 5 Season House

Premier Host

Beautiful Killington VT Ski & Mountain Bike 5 Season House

Sleeps 12 · 5 bedrooms · 2 bathrooms

Image of Killington area home - 4-seasons, hot tub and A/C

Premier Host

Killington area home - 4-seasons, hot tub and A/C

Sleeps 15 · 3 bedrooms · 2+ bathrooms

Image of Mountain Top - Fresh Pond - Killington - Hot Tub

Premier Host

Mountain Top - Fresh Pond - Killington - Hot Tub

Sleeps 14 · 4 bedrooms · 3+ bathrooms

Image of Silver Spring Chalet – Spacious 4BR Retreat in Killington Region, Pittsfield, VT, Sleeps 11

Silver Spring Chalet – Spacious 4BR Retreat in Killington Region, Pittsfield, VT, Sleeps 11

Sleeps 11 · 4 bedrooms · 3 bathrooms

Image of Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington

Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington

Sleeps 10 · 3 bedrooms · 2 bathrooms

Image of Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Sleeps 6 · 3 bedrooms · 2 bathrooms

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