
House vacation rentals in Stockbridge
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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 free parking

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Cozy Berkshire Getaway

Berkshires Forest Retreat with Hot Tub

Classic Stockbridge Cottage

New Shaw Pond Skytop Retreat in the Berkshires

Private Home in The Berkshires (New Hot Tub!)

Berkshires Black Abbey

Private NE Colonial walking distance to Lenox.
House rentals with a pool

Berkshires Oasis Retreat: Art Meets Nature

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Modern Barn on 12 acres w Sauna, FirePit+swimming

Hilltop: Panoramic Views w/ Pool near Catamount

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

Stylish, Secluded Getaway with Pool & Fireplace

Hudson Saltbox

Hilltop modern with stunning mountain views
Weekly house rentals

Magical Berkshires Farmhouse on 18 Glorious Acres!

Spacious & Family-Ready Home w/ Fenced Yard in Lee

Lenox Cottage

Modern and Stylish Country Lakeside Cottage

Cabin With a Beautiful Lake View

Charming Cottage - Walk To Town

The Red House

Meadowbrook Cottage
Quick stats about house rentals in Stockbridge
Total rentals
70 properties
Nightly prices starting at
€ 85 before taxes and fees
Total number of reviews
2.7K 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
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- Rentals with a fireplace Stockbridge
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- Hunter Mountain
- Six Flags New England
- John Boyd Thacher State Park
- Taconic State Park
- Bushnell Park
- Berkshire East Mountain Resort
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Zoom Flume
- Bash Bish Falls State Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Windham Mountain
- Beartown State Forest
- Hartford Golf Club
- Mohawk Mountain Ski Area
- Wintonbury Hills Golf Course
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Pineridge Cross Country Ski Area