Book Holiday Homes in Stockbridge
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Featured Holiday Homes in Stockbridge

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Stockbridge Village in Summer

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Spacious 5-bedroom house in charming Lee with WiFi

Amore Estate - beautiful room with many places to explore and relax in.

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

General Williams Estate House Lenox/Stockbridge

Cheerful 3-bedroom cottage with woodstove

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Stockbridge vacation homes are the perfect way for you to wing it.
Holiday houses in Stockbridge let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Stockbridge in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Stockbridge adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Stockbridge with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Stockbridge vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Stockbridge Holiday Homes essential information
Accommodation | 474 Holiday Homes |
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Lowest Price | AU$184 |
Highest Price | AU$1,254 |
Popular accommodation | Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Stockbridge Village in Summer, NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE, Spacious 5-bedroom house in charming Lee with WiFi, Amore Estate - beautiful room with many places to explore and relax in., Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location, General Williams Estate House Lenox/Stockbridge, Cheerful 3-bedroom cottage with woodstove, Walk into town, soak up sun on enclosed porch & steps away from nature trails! |
Top trending hotels in Stockbridge

The Red Lion Inn

Tanglewood Suites

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Vacation Village in the Berkshires
More ways to explore Stockbridge
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.