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Compare 43 Cottages in Pittsfield with updated reviews, rates, and availability.

Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers

Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers

Lake Hortonia 3 bedroom cottage and boat house 2 min walk to Lake.

Lake Hortonia 3 bedroom cottage and boat house 2 min walk to Lake.

Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock

10.0 out of 10, Exceptional, (11)
"We thoroughly enjoyed our stay at Lake Bomoseen. The house was in a great location with incredible lake views. The private dock was very relaxing."
Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice time, great location"
The price is AED 541
AED 1,632 total
includes taxes & fees
29 May - 30 May
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.2 out of 10, Wonderful, (17)
"We thoroughly enjoyed our stay at the cottage. We slept well and the location was perfect. We would like to visit again!"
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (53)
"Host was very friendly,, property was emaculate, would definitely stay here again"
The price is AED 489
AED 753 total
includes taxes & fees
29 May - 30 May
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (91)
"We loved the carriage house and its proximity to the town of Woodstock. Perfect to come home at the end of the day. Would definitely recommend to anyone visiting Woodstock! "
Woodstock Village Carriage House

New Lakeside Cottage near Okemo and Killington

9.6 out of 10, Exceptional, (153)
"Awesome for staying near killington!"
New Lakeside Cottage near Okemo and Killington

Idyllic Wallingford Retreat - Near Skiing & Hiking

3.0 star property
8.0 out of 10, Very Good, (2)
"This was the perfect place for 2 people to stay for a trip to Okemo. Everything we could have needed was available on the property, it was very clean and comfortable, and the hostess was great at communicating details ahead of time. Thanks for allowing us to use your property - I would love to return!"
Idyllic Wallingford Retreat - Near Skiing & Hiking

Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

10.0 out of 10, Exceptional, (9)
"If you’re looking to spend a weekend with some friends at Killington this is definitely the most bang for your buck outside of the resort. 20 minute drive and plenty of plowed parking. "
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

Inviting A-frame Cabin w/ Saltwater Hot Tub!

3.0 star property
Inviting A-frame Cabin w/ Saltwater Hot Tub!

Cozy Cabin Retreat

10.0 out of 10, Exceptional, (26)
"The property was perfect and quiet. The hosts were quick to respond and gave great directions and advice. Will definitely stay again."
The price is AED 525
AED 897 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Cabin Retreat

Rustic Roxbury Ski Farmhouse With Trails!

3.0 star property
Rustic Roxbury Ski Farmhouse With Trails!

Killington Area Escape w/ Deck, Views & Hot Tub!

3.0 star property
Killington Area Escape w/ Deck, Views & Hot Tub!

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

Lovely Brookfield Home w/ Private Deck & Views

3.0 star property
10.0 out of 10, Exceptional, (1)
" Lovely home, beautifully furnished "
Lovely Brookfield Home w/ Private Deck & Views

Pet-friendly Roxbury Farmhouse on 350 Acres!

3.0 star property
Pet-friendly Roxbury Farmhouse on 350 Acres!

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington

Mendon Home w/ Hot Tub, Fire Pit & Near Skiing!

3.0 star property
Mendon Home w/ Hot Tub, Fire Pit & Near Skiing!

11 Mi to Sugarbush: Eclectic Ski House w/ Hot Tub!

3.0 star property
11 Mi to Sugarbush: Eclectic Ski House w/ Hot Tub!
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.
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Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+

9.8 out of 10, Exceptional, (117)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 13+

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (43)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (243)
"Would definetly go back. Enjoyable, quiet, just an enjoyable stay!"
Cozy Loft for two with Hot Tub & Mtn Views
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.

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