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Compare 44 Cottages in Stockbridge with updated reviews, rates, and availability.

Newly converted 2BR/2BA carriage house!
10.0 out of 10, Exceptional, (2)
"This property is a hidden gem! Quaint, so cozy, adorably decorated! we absolutely loved everything about it! Wddidnt want to"
Newly converted 2BR/2BA carriage house!
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 SAR 413
SAR 673 total
includes taxes & fees
17 Nov - 18 Nov
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
9.6 out of 10, Exceptional, (9)
"This lake house is absolutely everything you would expect from a five star rated home. It is a newly renovated lake front home. The house is located about 3 miles north of Ludlow. The property was clean and well maintained. We visited on Columbus Day weekend for our daughter’s wedding. We will return some day in the summer to enjoy the lake. I would recommend this property to my family and friends. Thank you for sharing your home with us during this special time for our family. "
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Cozy Historic Hilltop Cottage with Mount Ascutney View
9.6 out of 10, Exceptional, (74)
"This house is exactly as described. It is in a very attractive location with good views and is very private. The house is much larger inside than it appears from the photos but still very cozy and is well equipped. It was spotlessly clean."
Cozy Historic Hilltop Cottage with Mount Ascutney View
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
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 SAR 492
SAR 870 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Cabin Retreat
The Carriage House on Main
9.8 out of 10, Exceptional, (16)
"Clean, quiet lovely property, close to our activities. We enjoyed our stay. Minor note: cooking equipment, utensils and related items are limited. Beds, linens and showers were great!"
The Carriage House on Main
Spruce Moose Cottage | Tiny House on 65 private acres
Spruce Moose Cottage | Tiny House on 65 private acres
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 cottage on the river, minutes from skiing, horse events, and so much more!
10.0 out of 10, Exceptional, (7)
"We loved our stay at the Dark Horse Cottage. It was close to everything we wanted to do. We loved being near the little creek. They thought of everything for amenities. It was perfect for what we needed. "
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
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
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!
3.0 star property
Historic Vermont Ski House w/ Mountain Views!
Rustic Roxbury Ski Farmhouse With Trails!
3.0 star property
Rustic Roxbury Ski Farmhouse With Trails!
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!
3.0 star property
Pet-friendly Roxbury Farmhouse on 350 Acres!
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
3.0 star property
Lakefront Paradise Near Okemo & Killington
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!
NEW LISTING Rustic Charm Meets Modern Comfort at Rock Haven Sugar House in Reading, VT
2.0 star property
10.0 out of 10, Exceptional, (1)
"Suited our needs perfectly! Close to what we were doing, quiet, peaceful, beautiful! Just the right amount of everything!"
NEW LISTING Rustic Charm Meets Modern Comfort at Rock Haven Sugar House in Reading, VT
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 Stockbridge

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (219)
"Very clean , everything we needed and more , beautiful hot tub , very cozy cabin nicely decorated "
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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