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Featured Cottages in Stockbridge

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
9.2 out of 10, Wonderful, (13)
"We liked the cottage and the tasteful renovations which preserved its historic nature. Loved the location's privacy and nature surrounding us. It was very warm over our stay and the AC units upstairs and down gave us more comfort. The linens were lovely, even if the mattress was a bit uncomfortable. There were no chairs on the deck and we wanted to sit outside often, so we bought inexpensive chairs and left them there. Our biggest complaint was with Vacasa's oversight. The cleaning crew did not...
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, (42)
"We attended a wedding in Goshen. It was a ten minute drive. It worked out perfectly. The home is very clean and comfortable! The host even turned the porch light on for us for our late night return. "
The price is AU$325
includes taxes & fees
14 Oct - 15 Oct
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
10.0 out of 10, Exceptional, (5)
"My daughter & I had a truly wonderful stay at this beautiful cottage conveniently located to downtown Woodstock that provides a quiet place to relax among the trees next to a babbling brook. The horse theme throughout the cabin is charming but the impeccable attention to detail is unmatched. Anything and everything you could want or need for a comfortable stay is provided. There is even a heated toilet seat and a mini bar! And the host's binder of local recommendations offers something for...
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Newly converted 2BR/2BA carriage house!
Newly converted 2BR/2BA carriage house!
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
9.6 out of 10, Exceptional, (7)
"This house has gorgeous views and a clean and tasteful interior. We found it even more beautiful than the pictures. There is a fully equipped kitchen and the beds are all very comfortable. You have to get in your car to go for a hike because it is off a main road, but that is the only downside. We would stay here again in a heartbeat. "
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Cozy Cabin Retreat
10.0 out of 10, Exceptional, (23)
"Great stay! Kitchen could use a toaster. No other complaints. "
The price is AU$373
includes taxes & fees
17 Oct - 18 Oct
Cozy Cabin Retreat
The Carriage House on Main
9.8 out of 10, Exceptional, (14)
"Great set up and lovely views from the front and back of this property. Clean and very well done barn renovation. Lots of space and loved to sit out on front porch. Our dog loved the wide open space to run and it was a short drive to everything the area has to offer."
The Carriage House on Main
Cozy Historic Hilltop Cottage with Mount Ascutney View
9.8 out of 10, Exceptional, (72)
"Had a great stay at the old school house. Location was perfect for what we needed. Place was super clean and well appointed. Would love to come back again."
Cozy Historic Hilltop Cottage with Mount Ascutney View
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, (5)
"Stayed here with some friends while attending a wedding in nearby Barnard. Place was spotless and quite comfortable. No AC so we really appreciated the fans every room. The star attraction, however, is the riverside fire pit. Wow! What an amazing spot to while away a summer afternoon, swimming, warming up by the fire, catching up with old friends."
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
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!
Riverfront Vermont Vacation Rental w/ Hot Tub
3.0 star property
Riverfront Vermont Vacation Rental w/ Hot Tub
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
The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!
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See all available properties in Stockbridge
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

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (464)
"If you’re looking for rest and relaxation this is it. You are one with nature at this cabin which has everything you need. Host was very nice and accommodating. Plenty of yard games for the family and trails to explore. Hope to be back in the future. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (209)
"Jeff is a very gracious host and kept in communication throughout this VRBO experience. The cabin is a wonderfully enchanting place with a lot of privacy, and everything you need to make your time spent there a very relaxing and rewarding experience. The cabin is within 20 minutes of Stowe, Vt. The culture is downhome and the food is great!!!!"
Cozy Loft for two with Hot Tub
Cozy Studio for 4 - Walk to Mountain w/ Balcony
8.8 out of 10, Excellent, (16)
"We traveled for the Killington Spartan race and this lodging met our needs perfectly. It’s was conveniently located directly across from the shuttle pick up. Also we were able to walk to a nearby restaurant for a delicious dinner. The condo was very clean and had everything we needed. Lars communicated frequently with everything we needed to know. I would definitely stay again! "
The price is AU$292
includes taxes & fees
30 Sept - 1 Oct
Cozy Studio for 4 - Walk to Mountain w/ Balcony
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.

Frequently asked questions

What is there to do in Stockbridge near my cottage?
The most practical travel accessory is a well-planned schedule. Little Pico Mountain is a great place to kick-start your exploration of Stockbridge.