Book Holiday Homes in Stockbridge
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Featured Holiday Homes in Stockbridge

Beautifully renovated with fireplace and coffee bar

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

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

Spacious country home, beautiful sunsets, 40 acres

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
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 | 727 Holiday Homes |
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Lowest Price | AU$190 |
Highest Price | AU$731 |
Popular accommodation | Beautifully renovated with fireplace and coffee bar, Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you, Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee, Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont, Spacious country home, beautiful sunsets, 40 acres, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, ☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace, Dog-friendly house with picturesque mountain view & near skiing - close to Okemo |
Top Locations for Holiday Homes in Stockbridge
More accommodations in Stockbridge
Top trending hotels in Stockbridge

Comfort Inn Rutland - Killington

Align Inn Vermont

Killington Mountain Lodge, Tapestry Collection by Hilton

Woodstock Inn & Resort
More ways to explore Stockbridge
Top picks
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^Subject to availability and chosen travel dates.