Book Holiday Homes in Stockbridge
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Featured Holiday Homes in Stockbridge

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

Pet-Friendly, Heart of Quechee | Jay Hill Home

The Old Orchard Home surrounded by a small apple orchard, large meadows, and a private pond

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

Spacious country home, beautiful sunsets, 40 acres

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Heated Saltwater Pool: Riverfront Home in Ludlow

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
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 | 773 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you, Pet-Friendly, Heart of Quechee | Jay Hill Home, The Old Orchard Home surrounded by a small apple orchard, large meadows, and a private pond, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Spacious country home, beautiful sunsets, 40 acres, Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak, Heated Saltwater Pool: Riverfront Home in Ludlow, 5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!, Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski |
Top Locations for Holiday Homes in Stockbridge
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Top trending hotels in Stockbridge

Ski/MTB Sleeps 20 home w/ mountain views near Killington/Woodstock. Rent 2 units

Align Inn Vermont

Woodstock Inn & Resort

Comfort Inn Rutland - Killington
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^Subject to availability and chosen travel dates.