Best Pittsfield Holiday Cottages in 2025

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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.

Immerse yourself in local style in Pittsfield Cottages

Pittsfield Cottages essential information

Accommodation
35 Cottages
Lowest Price
€186
Highest Price
€491
Popular accommodation
Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock, Pristine Custom Cottage, Grand Piano, Massage Studio on Site, Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers, Cozy 1850s home on the riverfront with mountain & river views - dog-friendly, Woodstock Village Vaunutalo, The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland., Cozy Cabin Retreat, Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains, Idyllic Wallingford Retreat - Near Skiing & Hiking, Rustic Roxbury Ski Farmhouse With Trails!, Pet-friendly Roxbury Farmhouse on 350 Acres!, Lovely Brookfield Home w/ Private Deck & Views, Killington Area Escape w/ Deck, Views & Hot Tub!, Picture-perfect Vermont Mtn Cabin w/ Hot Tub!, Lakefront Paradise Near Okemo & Killington