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

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, (48)
"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 AED 459
AED 728 total
includes taxes & fees
8 Dec - 9 Dec
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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
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."
The price is AED 500
AED 876 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Cabin Retreat
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
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!
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!
Home w/ Sauna - Close to Pico & Killington Mtns!
Living area
Home w/ Sauna - Close to Pico & Killington Mtns!
3.0 star property
Home w/ Sauna - Close to Pico & Killington Mtns!
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
New! South Woodstock Cottage - restored, modern luxury
New! South Woodstock Cottage - restored, modern luxury
New! South Woodstock Cottage - restored, modern luxury
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!
Private kitchen
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!
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, (113)
"We stayed for a small bachelor party and had a great time! Everyone had room and there was plenty to do."
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, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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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