Book Holiday Homes in Stockbridge
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We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Stockbridge
Berkshire Village Carriage House - Super Private!!
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Spectacular views and close to Great Barrington.
Peace and quiet on the lake
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Lakeview Retreat - mins. to downtown Lenox, Stockbridge, Lee
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Beautiful Berkshire Farm House on 160+ Acres
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 | 348 Holiday Homes |
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Lowest Price | NZ$171 |
Highest Price | NZ$383 |
Popular accommodation | Berkshire Village Carriage House - Super Private!!, Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con, Spectacular views and close to Great Barrington., Peace and quiet on the lake, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Lakeview Retreat - mins. to downtown Lenox, Stockbridge, Lee, Berkshire Ski House on Lake Garfield w/HT By Great Barrington , Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond, Beautiful Berkshire Farm House on 160+ Acres |
More accommodations in Stockbridge
Top trending hotels in Stockbridge
The Red Lion Inn
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
More ways to explore Stockbridge
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.