
House holiday rentals in Stockbridge
Find and book unique houses on Airbnb
Top-rated house rentals in Stockbridge
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Stockbridge
House rentals with a pool

Pond, Pool, Mountain Views | Au Bout du Chemin

Epic Views of the Green Mountains

Ranch at Mendon Mt Orchards

Charming Sugarbush Standalone Condo

Private Farmhouse with in ground pool!

Comfortable, relaxing large country home

Historic Home on 17 acres of land. Go escape!

Luxurious family retreat home in the mountains
Weekly house rentals

Charming Vermont Schoolhouse

Skyeburst | Modern Mtn Home

Chalet Suite | 2BR+Loft (Secure Mtn Bike Storage)

Entire home- Killington, Vermont Ski, Hike, Bike

Romantic Retreat, Hot Tub, near Killington Mtn

Barn Hollow Farm

150 acres of serenity at Light Hill in Barnard, VT

The Creek House in Barnard near Woodstock
Private house rentals

BEST Views! Close to Silver Lake + Woodstock VT

Quaint Cottage

Fabulous Log Home in the Woods

THE BIJOU @ Green Mountains ~ A Precious Gem

Green Mountain/Killington Getaway

Stylish Ascutney Cabin •View •Chef’s Kitchen •Pets

The Barn at Cold River ~ 20 minutes to Ski Resorts

Great Find. Spacious. Dogs are Welcome (Limit 2)
Quick stats about house rentals in Stockbridge
Total rentals
30 properties
Nightly prices starting at
€ 76 before taxes and fees
Total number of reviews
980 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
- Montreal Holiday rentals
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- Philadelphia Holiday rentals
- Rentals with a washing machine and dryer Stockbridge
- Rentals with a firepit Stockbridge
- Family-friendly rentals Stockbridge
- Rentals with a fireplace Stockbridge
- Rentals with outdoor seating Stockbridge
- Family-friendly rentals Stockbridge
- Pet-friendly rentals Stockbridge
- Rentals with a patio Stockbridge
- Rentals with a hot tub Stockbridge
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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Bolton Valley Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Bromley Mountain Ski Resort
- Country Club of Vermont
- Fox Run Golf Club
- Baker Hill Golf Club
- Northeast Slopes Ski Tow
- Cozy Cottages & Otter Valley Winery
- Ekwanok Country Club
- Vermont National Country Club
- Lucky Bugger Vineyard & Winery
- Adirondack Extreme Adventure Course
- Lincoln Peak Vineyard