
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

Fish, Bike, Golf, or Hike!

Epic Views of the Green Mountains

Ranch at Mendon Mt Orchards

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Charming Sugarbush Standalone Condo

Dana Road House Sunlit VT Country Home w/HotTub

Historic Home on 17 acres of land. Go escape!
Weekly house rentals

Charming Vermont Schoolhouse

Skyeburst | Modern Mtn Home

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

Private Farmhouse w/ River Access Fly Fishing Hole

Fred Eddy Farmhouse

Hideaway Mountain at Killington

*New* Skye Ridge Lodge: 3 Bd, Hot Tub, Fireplace

Romantic Retreat, Hot Tub, near Killington Mtn
Private house rentals

19th Century Bohemian Barn House

BEST Views! Close to Silver Lake + Woodstock VT

Cute & cozy 2 bedroom home.

Cottage in the middle of family horse farm

Barn Hollow Farm

150 acres of serenity at Light Hill in Barnard, VT

Architectural House Prickly Mountain

Rockwell Haus: modern cabin 14 min from Killington
Quick stats about house rentals in Stockbridge
Total rentals
30 properties
Nightly prices starting at
₹7,928 before taxes and fees
Total number of reviews
1K 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
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Pet-friendly rentals Stockbridge
- Rentals with a patio Stockbridge
- Rentals with a fireplace Stockbridge
- Rentals with a washing machine and dryer Stockbridge
- Rentals with outdoor seating Stockbridge
- Family-friendly rentals Stockbridge
- Rentals with a hot tub Stockbridge
- Rentals with a firepit Stockbridge
- House rentals Windsor County
- House rentals Vermont
- House rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Magic Mountain Ski Resort
- Fort Ticonderoga
- Tenney Mountain Resort
- Bolton Valley Resort
- Dartmouth Skiway
- Stratton Mountain Resort
- Dorset Field Club
- Cochran's Ski Area
- Pico Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Lucky Bugger Vineyard & Winery
- Ekwanok Country Club
- Fox Run Golf Club
- Montshire Museum of Science
- Autumn Mountain Winery
- Whaleback Mountain
- Northeast Slopes Ski Tow
- Mount Sunapee Resort
- Baker Hill Golf Club
- Adirondack Extreme Adventure Course
- Killington Adventure Center