
House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Stockbridge house rentals
House rentals with a pool

Private lakefront home, hot tub & resort amenities

Poolside Woodlawn Getaway

The Catamount Ski Haus with Pool & Hot Tub

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Modern Barn on 12 acres w Sauna, FirePit+swimming

Red Rock Summit: Mtn Escape w/ Pool, Pond + Views

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

Stylish Rural Sanctuary! (+ Summer Pool)
Weekly house rentals

Waterfront Modern Lake Mansfield Retreat

Cozy. Clean. Free bagel shop.

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

The Red House

Historic Stone Church in The Berkshires

Berkshires Black Abbey

West Stockbridge Sanctuary by Evergreen Home

Lakefront Retreat -Private Dock,creek,and Fire pit
Private house rentals

Stunning Fall Views! Hot Tub/Movie Room/Game Room

Stockbridge Cape Near Tanglewood!

Charming Stockbridge Farmhouse- walk to town!

Meadowbrook Cottage

Charming Cottage - Walk To Town

Sauna + Hot Tub Escape | Private & Pet Friendly

Secluded Mountain and Lake View in Canaan, NY

Hot Tub, Canoe, Hike, Dog Friendly, Berkshires!
Quick stats about house rentals in Stockbridge
Total rentals
70 properties
Nightly prices starting at
€ 94 before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Plainview Vacation rentals
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- Rentals with a fire pit Stockbridge
- Family-friendly rentals Stockbridge
- Rentals with breakfast Stockbridge
- Rentals with a fireplace Stockbridge
- Rentals with beach access Stockbridge
- Rentals with a patio Stockbridge
- Rentals with outdoor seating Stockbridge
- Rentals with a washer and dryer Stockbridge
- Rentals with pools Stockbridge
- Rentals with lake access Stockbridge
- Hotel rentals Stockbridge
- Rentals with a hot tub Stockbridge
- Pet-friendly rentals Stockbridge
- House rentals Berkshire County
- House rentals Massachusetts
- House rentals United States
- Hunter Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Catamount Mountain Ski Resort
- Bushnell Park
- Mount Greylock Ski Club
- Windham Mountain
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Taconic State Park
- Mount Sugarloaf State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Mount Tom State Reservation
- Beartown State Forest
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park