Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

4 Season Secluded Lakefront Home near Ski Mountains

Mt Holly VT

Located in Mount Holly, this vacation home is on the waterfront, within a 15-minute drive of Lake Ninevah and Buttermilk Falls.

Kitchen

Washer

Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning

Killington VT

With a stay at this vacation home in Killington, you'll be within a 10-minute drive of Killington Resort and Pico Mountain at Killington Ski Resort.

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Plymouth VT

With a stay at this vacation home, you'll be centrally located in Plymouth, within a 10-minute drive of Amherst Lake and Echo Lake.

Hot Tub

Kitchen

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Bridgewater Corners VT

When you stay at this vacation home in Bridgewater Corners, you'll be on a lake, within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski Resort.

Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

west rutland VT

Located in West Rutland, this vacation home is on the waterfront, within a 15-minute drive of Clarendon Town Hall and Airport Driving Range.

Kitchen

Washer

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.

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Killington VT

With a stay at this vacation home in Killington, you'll be within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski Resort.

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

Killington VT

When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and a 3-minute drive from Sunrise Village Triple Ski Lift.

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington VT

When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and 15 minutes by foot from Sunrise Village Triple Ski Lift.

Spectacular 4 Bed Killington Home

Killington VT

When you stay at this vacation home in Killington, you'll be in the mountains, a 2-minute drive from Killington Resort and 8 minutes from Pico Mountain at Killington Ski Resort.

Killington Vermont Ski and Snowmobiling House

Pittsfield VT

Located in Pittsfield, this vacation home is within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski Resort.

Classic Vermont Farmhouse near Sugarbush Resort

Warren VT

With a stay at this vacation home in Warren, you'll be in the mountains, within a 10-minute drive of Sugarbush Ski Resort and Green Mountain National Forest.

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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.