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Compare 38 Cottages in Stockbridge with updated reviews, rates, and availability.

Cozy cottage on the river, minutes from skiing, horse events, and so much more!
10.0 out of 10, Exceptional, (1)
"We had a great stay! The cottage is extremely clean and very well put together. Every amenity you could think of is there! They definitely thought of all of the little touches!"
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Luxurious Secluded Cottage Massage Studio on Site November & December Discounts
10.0 out of 10, Exceptional, (34)
"Beautiful cottage equipped with everything you might need. Incredibly clean, comfortable and a helpful, friendly host."
The price is $165
$240 total
includes taxes & fees
May 9 - May 10
Luxurious Secluded Cottage Massage Studio on Site November & December Discounts
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
10.0 out of 10, Exceptional, (3)
"Clean, spacious, well equipped kitchen, nice hot tub, and loved the fire pit by the river."
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
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Lovely Brookfield Home W/private Deck & Views
3.5 star property
10.0 out of 10, Exceptional, (1)
" Lovely home, beautifully furnished "
Lovely Brookfield Home W/private Deck & Views
Ronnoco Farm-Charming Brownsville/West Windsor, VT cottage
10.0 out of 10, Exceptional, (8)
"Cottage is lovely; very well equipped and super comfortable. Stunning surroundings if you’re looking for peace and quiet. Great for walks and exploring the countryside. Would definitely stay there again."
Ronnoco Farm-Charming Brownsville/West Windsor, VT cottage
Cozy Cottage near Woodstock VT and skiing!
10.0 out of 10, Exceptional, (1)
"We were looking to ski in Killington. On the map which is not the owner's fault it showed that it was only 10 to 12 miles away. Really it's a two-and-a-half-hour round trip. The mud prevented us from staying our last night which we paid for. It was way too sketchy for me to drive on."
Cozy Cottage near Woodstock VT and skiing!
Cozy Cabin Retreat
9.8 out of 10, Exceptional, (19)
"Wonderful place, just need to fill in holes and level the driveway out, especially at the garage. Hope to stay again one day, but I plan on driving my corvette next time, which sits low to the ground. Also, they are serious about no cellular service, but I enjoyed the quietness without my phone working."
Cozy Cabin Retreat
Renovated lakefront cottage with deep-water dock, swim platform, & firepit
9.6 out of 10, Exceptional, (4)
"Location was awesome, house met the description and was comfortable. Stayed with dog and 3 kids. Doors (or walls?) were a little drafty in the winter, but heating seemed to be ok. Heated floors in bathrooms were really nice. Suggest more than 2 dishwasher tabs per renter. Basement is quite cold but we didn't need to use it for sleeping. Still, 5 stars, great property and would stay again."
Renovated lakefront cottage with deep-water dock, swim platform, & firepit
Cottage Across Street from the Lake w/ 60' Water Frontage Access, Private Dock
9.0 out of 10, Wonderful, (45)
"The house is super nice and cozy, but there was a lot of mud in the parking lot, making things quite difficult to pack and unpack the car. The WiFi signal was good, but super low speed. Other than these two things, we loved the place and would recommend it, specially because it is very close to Okemo Ski resort."
Cottage Across Street from the Lake w/ 60' Water Frontage Access, Private Dock
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
8.6 out of 10, Excellent, (7)
"The home is charming, immaculate and amidst woods with no neighbors in eye or earshot. It is on a dirt road, so an awd vehicle is a good idea. A stream runs along the driveway. The Ottauquechee River is across the road. The bathroom is on the first floor, and bedrooms on the second floor. The smoke detector goes off if you saute on the stove. I recommend learning how to turn off a wired in smoke detector. You should open the kitchen window when you saute, because most of the smoke detectors...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Spruce Moose Cottage | Tiny House on 65 private acres
Spruce Moose Cottage | Tiny House on 65 private acres
Newly converted 2BR/2BA carriage house!
Newly converted 2BR/2BA carriage house!
Historic Vermont Ski House w/ Mountain Views!
3.5 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!
3.5 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
3.5 star property
Lakefront Paradise Near Okemo & Killington
Vermont Retreat - 8 Mi to Killington Ski Area
3.5 star property
Vermont Retreat - 8 Mi to Killington Ski Area
Newly remodeled cottage at Lake Dunmore!
Newly remodeled cottage at Lake Dunmore!
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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.

Other property types in Stockbridge

Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (192)
"Relaxing cabin close enough to take a day trip to the bigger cities but remote enough to get away from it all"
Cozy Loft for two with Hot Tub
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (445)
"Cabin was exactly as advertised. So much information provided made check in and out incredibly easy. Highly recommend."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (9)
"This is an adorable spot! Super quiet, the treehouse is very unique, and moments away from downtown Woodstock. We’ll be back!"
The price is $150
$184 total
includes taxes & fees
May 7 - May 8
Treehouse at Wise Pines- SoBo
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.

Stockbridge Cottages information

Number of reviews
94
Accommodation
38 Cottages
Lowest Price
$165
Highest Price
$165

Frequently asked questions

Why book your cottage in Stockbridge with Expedia?
Expedia has some terrific cottages in Stockbridge, so get set for an unforgettable stay on nature’s doorstep. If you have a budget, select how much you’re willing to spend and the star rating of your property. Or take advantage of our filters to search for cottages with a hot tub or a kitchen. We’ll help you find the right fit whatever your getaway looks like.
How can I find cheap cottages in Stockbridge?
With Expedia’s useful filter tool, scoring cheap cottages in Stockbridge is a breeze. To find properties that are friendly on the wallet, refine your search by budget, amenities and star rating.
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.

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