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Compare 34 Cottages in Pittsfield with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (7)
"Obsessed with this house! It was perfect for 2 couples and our pups for a relaxing fall weekend. Rooms were cozy, updated and super clean. The hot tub, fire pit by the river and big kitchen were highlights. I really appreciated the hospitality of having amenities like spices, coffee filters, shampoo & conditioner, laundry detergent, etc. Would book again!"
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

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

9.2 out of 10, Wonderful, (15)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Living area

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (49)
"Our stay at Camp Tiger Ted was so wonderful. The amount of detail and care David put into building and now maintaining the property is second to none. The house was meticulously clean and had so many charming details. David also gave us both massages in his in home studio which waA the most relaxing way to end our stay!"
The price is SAR 469
SAR 736 total
includes taxes & fees
30 Dec - 31 Dec
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Cozy Cabin Retreat
Exterior

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."
Cozy Cabin Retreat
Lovely Brookfield Home w/ Private Deck & Views
Dining

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
Idyllic Wallingford Retreat - Near Skiing & Hiking
Dining

Idyllic Wallingford Retreat - Near Skiing & Hiking

3.0 star property
Idyllic Wallingford Retreat - Near Skiing & Hiking
Inviting A-frame Cabin w/ Saltwater Hot Tub!
Exterior

Inviting A-frame Cabin w/ Saltwater Hot Tub!

3.0 star property
Inviting A-frame Cabin w/ Saltwater Hot Tub!
Historic Vermont Ski House w/ Mountain Views!
Exterior

Historic Vermont Ski House w/ Mountain Views!

3.0 star property
Historic Vermont Ski House w/ Mountain Views!
Rustic Roxbury Ski Farmhouse With Trails!
Living area

Rustic Roxbury Ski Farmhouse With Trails!

3.0 star property
Rustic Roxbury Ski Farmhouse With Trails!
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Outdoor dining

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Killington Area Escape w/ Deck, Views & Hot Tub!
Terrace/patio

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

3.0 star property
Killington Area Escape w/ Deck, Views & Hot Tub!
Pet-friendly Roxbury Farmhouse on 350 Acres!
Living area

Pet-friendly Roxbury Farmhouse on 350 Acres!

3.0 star property
Pet-friendly Roxbury Farmhouse on 350 Acres!
Lakefront Paradise Near Okemo & Killington
Property grounds

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington
Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock
Dock at Sunset

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

9.8 out of 10, Exceptional, (10)
"Cottage was very clean and stocked with basic essentials. Owner was very responsive to our texts and communicated well. Great view of lake from cabin. We had a wonderful stay and hope to go back some day."
Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock
The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!

The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Property was very comfortable. Check-in was simple, plenty of communication and prompt replies. Would absolutely stay at this property again. "
The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!
Vermont Retreat - 8 Mi to Killington Ski Area
Terrace/patio

Vermont Retreat - 8 Mi to Killington Ski Area

3.0 star property
Vermont Retreat - 8 Mi to Killington Ski Area
Newly remodeled cottage at Lake Dunmore!
Upstairs terrace with lake view!

Newly remodeled cottage at Lake Dunmore!

Newly remodeled cottage at Lake Dunmore!
Duplex Unit, 2 Mi to Chittenden Reservoir!
Bar (on property)

Duplex Unit, 2 Mi to Chittenden Reservoir!

3.0 star property
Duplex Unit, 2 Mi to Chittenden Reservoir!
Remote Escape: Vermont Cabin w/ Mountaintop Views!
Dining

Remote Escape: Vermont Cabin w/ Mountaintop Views!

2.0 star property
Remote Escape: Vermont Cabin w/ Mountaintop Views!
Luxe Plymouth Chalet w/ Indoor Pool & 3 Decks!
Living area

Luxe Plymouth Chalet w/ Indoor Pool & 3 Decks!

3.0 star property
Luxe Plymouth Chalet w/ Indoor Pool & 3 Decks!
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 12+
Here's the main living area - dining is up on the left

Killington area home - 4-seasons & hot tub. Sleeps 12+

9.8 out of 10, Exceptional, (114)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 12+
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"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
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (222)
"We had the best time at Jeff’s perfect cozy ‘little loft’! It exceeded expectations! We especially enjoyed the hot tub after long days of skiing!"
Cozy Loft for two with 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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