Book Holiday Homes in Stockbridge
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Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Stockbridge

4 Season Secluded Lakefront Home near Ski Mountains

Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
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 | 644 Holiday Homes |
|---|---|
Lowest Price | NZ$333 |
Highest Price | NZ$853 |
Popular accommodation | 4 Season Secluded Lakefront Home near Ski Mountains , Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning, Rustic home with a private hot tub, fireplace, cable, & washer/dryer, Renovated Retreat • Fireplace • Coffee Bar • Minutes to Skiing & Woodstock, Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola, Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts, Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you, Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!, PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC. |
Top trending hotels in Stockbridge

Killington Mountain Lodge, Tapestry Collection by Hilton

Woodstock Inn & Resort

The Mountain Inn at Killington

White River Inn and Suites
More ways to explore Stockbridge
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
