Pittsfield Vacation Rentals
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Vacation Rentals in Pittsfield
Recently updated home with shared hot tub, pool, and easy ski access
Killington VT
With a stay at this vacation home in Killington (The Woods), you'll be within a 10-minute drive of Killington Resort and Green Mountain National Forest.
Pool
Hot Tub
Cozy 3BR Mountain home near Sugarbush, beside the original Lawson's Brewery
Warren VT
With a stay at this vacation home in Warren, you'll be within a 10-minute drive of Sugarbush Ski Resort and Moosewalk Studios and Gallery.
Kitchen
Washer
Roundabout Ridge
Killington VT
Located in Killington, this vacation home is in the mountains, within a 10-minute drive of Skyeship Express Gondola Stage II and Northbrook Quad Ski Lift.
Kitchen
Washer
Fantastic 6-bedroom house in Mendon Vermont - Killington / Pico
Rutland VT
With a stay at this vacation home in Rutland, you'll be within a 5-minute drive of Green Mountain National Forest and Green Mountain Rock Climbing Center.
Washer
Dryer
BRIDGEWATER RETREAT
Bridgewater VT
With a stay at this vacation home in Bridgewater Corners, you'll be in the mountains, within a 10-minute drive of Killington Resort and Skyeship Express Gondola Stage I.
Pool
Kitchen
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Hartford VT
Located in White River Junction, this vacation home is a 1-minute drive from Quechee Ski Hill and 7 minutes from The Strong House Spa.
Pool
Kitchen
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Woodstock VT
Located in Woodstock, this vacation home is in a rural location, within a 10-minute drive of Union Arena Community Center and Five Elm Arches.
Kitchen
Washer
Cozy private country setting - 15 miles from Woodstock
Royalton VT
Located in Bethel, this vacation home is in the mountains, within a 10-minute drive of Bethel Public Library and Day Breaks Glass Studio.
Kitchen
Free WiFi
Walk to Pickle Barrel & Jax. Hot tub & Views
Killington VT
With a stay at this vacation home in Killington, you'll be in the mountains, within a 5-minute drive of Killington Resort and Gifford Woods State Park.
Kitchen
Washer
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
Plymouth VT
Located in Plymouth, this vacation home is in a rural location, within a 5-minute drive of Amherst Lake and Echo Lake.
Kitchen
Washer
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.
Pittsfield Vacation Rentals essential information
Accommodation | 559 Vacation Rentals |
|---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Recently updated home with shared hot tub, pool, and easy ski access, Cozy 3BR Mountain home near Sugarbush, beside the original Lawson's Brewery, Roundabout Ridge, Fantastic 6-bedroom house in Mendon Vermont - Killington / Pico, BRIDGEWATER RETREAT, Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont, PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC., Cozy private country setting - 15 miles from Woodstock, Walk to Pickle Barrel & Jax. Hot tub & Views, Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola, ☆ SKI ON/OFF! ☆ Luxe 2BR+ Trailside! Steam Shower, hot tub, pool, gym +more, ☆ SKI ON & OFF ☆ Spruce Glen C on Great Eastern Trail w/AC, Sauna, Fireplace |