Book Holiday Homes in West Stockbridge
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Featured Holiday Homes in West Stockbridge

Deluxe Queen Room with 2 Queen Beds

4 Mi to Great Barrington: Berkshires Retreat!

Large Barn styled vacation home that fits groups with space to spare.

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Stay Lakeside This Summer!

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

Spectacular views and close to Great Barrington.

Rustic 3bd Lake Front Country Cottage

Garfield Townhouse in the Berkshires on Main St
West 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 West Stockbridge vacation homes are the perfect way for you to wing it.
Holiday houses in West 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 West 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 West Stockbridge adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in West 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 West 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.
West Stockbridge Holiday Homes essential information
Accommodation | 530 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Deluxe Queen Room with 2 Queen Beds, 4 Mi to Great Barrington: Berkshires Retreat!, Large Barn styled vacation home that fits groups with space to spare. , Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, Stay Lakeside This Summer!, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Spectacular views and close to Great Barrington., Rustic 3bd Lake Front Country Cottage, Garfield Townhouse in the Berkshires on Main St |
More accommodations in West Stockbridge
Top trending hotels in West Stockbridge

Pleasant Valley Motel West Stockbridge

Shaker Mill Inn

Quality Inn

The Yankee, Trademark Collection by Wyndham
More ways to explore West Stockbridge
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^Subject to availability and chosen travel dates.