Book Holiday Homes in Stockbridge
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Featured Holiday Homes in Stockbridge

Spacious Home nestled along the Blackberry River in Northwest CT

Peace and quiet on the lake

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Deluxe Queen Room with 2 Queen Beds

Spectacular views and close to Great Barrington.

Taconic Hideaway – Swimming, BBQ Pit, Hiking

Falls Reach In The Heart of Copake

Poolside Luxe at Long Pond
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$202 |
Highest Price | AU$728 |
Popular accommodation | Spacious Home nestled along the Blackberry River in Northwest CT, Peace and quiet on the lake, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. , Deluxe Queen Room with 2 Queen Beds, Spectacular views and close to Great Barrington., Taconic Hideaway – Swimming, BBQ Pit, Hiking, Falls Reach In The Heart of Copake, Poolside Luxe at Long Pond |
Holiday Homes in Stockbridge
Top Locations for Holiday Homes in Stockbridge
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The Red Lion Inn

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

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