Best Pittsfield Holiday Cottages in 2025
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Featured Cottages in Pittsfield
Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock
Castleton, VT
During your stay at this cottage, you're just a quick walk from Lake Bomoseen. The cottage offers free WiFi and a kitchen.
Keittiö
Ilmainen Wi-Fi
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester, VT
The price is €186 per night
€186
includes taxes & fees
13 Mar - 14 Mar
During your stay at this cottage, you'll be within walking distance of Leicester Town Hall. Features include free breakfast. Free WiFi and a kitchen are available in the cottage.
Aamiainen sisältyy hintaan
Keittiö
Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers
West Rutland, VT
During your stay at this cottage, you'll be close to Wilson Castle. Features include breakfast (surcharge) and 1 hot tub. The cottage offers free WiFi and in-room jetted baths.
Poreallas
Keittiö
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Woodstock, VT
During your stay at this cottage, you're just a quick walk from Taftsville Covered Bridge. The cottage offers a kitchen and a fireplace.
Keittiö
Pyykinpesukone
Woodstock Village Vaunutalo
Woodstock, VT
During your stay at this cottage, you're just a quick walk from Marsh-Billings-Rockefeller National Historical Park. A kitchen and a sofa bed are available in the cottage.
Keittiö
Pyykinpesukone
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon, VT
The price is €491 per night
€491
includes taxes & fees
10 Mar - 11 Mar
During your stay at this cottage, you're just a quick walk from Green Mountain National Forest. Enjoy your stay with amenities like free WiFi and a kitchen in the cottage.
Keittiö
Pyykinpesukone
Cozy Cabin Retreat
Roxbury, VT
During your stay at this cottage, you're just a quick walk from Mad River Valley. Enjoy your stay with amenities like free WiFi and a kitchen in the cottage.
Keittiö
Ilmainen Wi-Fi
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Stockbridge, VT
During your stay at this cottage, you'll be close to Rood State Park. You'll find features such as 1 hot tub. The cottage offers free WiFi and a kitchen.
Poreallas
Keittiö
Idyllic Wallingford Retreat - Near Skiing & Hiking
Wallingford, VT
During your stay at this cottage, you're just a quick walk from Wallingford Town Hall. Enjoy features like free WiFi in public areas and free self-parking. A kitchen and a fireplace are available in the cottage.
Keittiö
Pysäköinti sisältyy hintaan
Rustic Roxbury Ski Farmhouse With Trails!
Roxbury, VT
During your stay at this cottage, you'll be close to Granville Gulf Reservation. Features include free WiFi in public areas and free self-parking. Enjoy your stay with amenities like a kitchen and 2.5 bathrooms in the cottage.
Keittiö
Lemmikkiystävällinen
Pet-friendly Roxbury Farmhouse on 350 Acres!
Roxbury, VT
During your stay at this cottage, you'll be close to Granville Gulf Reservation. You'll find features such as free WiFi in public areas and free self-parking. Enjoy your stay with amenities like a kitchen and a TV in the cottage.
Keittiö
Lemmikkiystävällinen
Lovely Brookfield Home w/ Private Deck & Views
Brookfield, VT
During your stay at this cottage, you'll be close to Brookfield Free Public Library. Enjoy features like free WiFi in public areas and free self-parking. The cottage offers a kitchen and 3 bathrooms.
Keittiö
Pysäköinti sisältyy hintaan
Killington Area Escape w/ Deck, Views & Hot Tub!
Stockbridge, VT
During your stay at this cottage, you're just a quick walk from Green Mountain National Forest. Features include free WiFi in public areas and free self-parking. Enjoy your stay with amenities like a kitchen and 2 bathrooms in the cottage.
Keittiö
Pysäköinti sisältyy hintaan
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Bridgewater Corners, VT
During your stay at this cottage, you'll be close to Long Trail Brewing Company. Enjoy features like free WiFi in public areas and free self-parking. The cottage offers a kitchen and 3 bathrooms.
Keittiö
Lemmikkiystävällinen
Lakefront Paradise Near Okemo & Killington
Mount Holly, VT
During your stay at this cottage, you're just a quick walk from Lake Ninevah. Enjoy features like free WiFi in public areas and free self-parking, plus an arcade/games room. A kitchen and 4.5 bathrooms are available in the cottage.
Keittiö
Pysäköinti sisältyy hintaan
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 |
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