Book Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

Deluxe Queen Room with 2 Queen Beds

Deluxe Queen Room with 2 Queen Beds

2 out of 5
Lee
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Deluxe Queen Room with 2 Queen Beds
4 Mi to Great Barrington: Berkshires Retreat!

4 Mi to Great Barrington: Berkshires Retreat!

Sheffield
Located in Great Barrington, this vacation home is a 3-minute drive from Housatonic River and 6 minutes from Thom Reed UFO Monument Park.
4 Mi to Great Barrington: Berkshires Retreat!
Large Barn styled vacation home that fits groups with space to spare.

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

Craryville
With a stay at this vacation home in Copake Lake, you'll be on the waterfront, just a 1-minute walk from Copake Lake and 13 minutes by foot from Mosquito ...
Large Barn styled vacation home that fits groups with space to spare.
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Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

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

Valatie
Located in Valatie, this vacation home is on the waterfront, a 1-minute drive from Kinderhook Lake and 6 minutes from Valatie Family Care.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Stay Lakeside This Summer!

Stay Lakeside This Summer!

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 10-minute drive of Art et Industrie and Housatonic River.
Stay Lakeside This Summer!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge
With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Stockbridge Bowl.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.
Spectacular views and close to Great Barrington.
Rustic 3bd Lake Front Country Cottage

Rustic 3bd Lake Front Country Cottage

Monterey
Located in Monterey, this vacation home is on the waterfront, within a 10-minute drive of Bidwell House Museum and Dry Hill.
Rustic 3bd Lake Front Country Cottage
Garfield Townhouse in the Berkshires on Main St

Garfield Townhouse in the Berkshires on Main St

Lee
With a stay at this vacation home in Lee, you'll be within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.
Garfield Townhouse in the Berkshires on Main St
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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
464 Holiday Homes
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

Top trending hotels in Stockbridge

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic ...
The Red Lion Inn
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
With a stay at Tanglewood Suites in Stockbridge, you'll be in the mountains, within a 10-minute drive of Tanglewood Music Center and Housatonic River.
Tanglewood Suites
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
With a stay at Quality Inn in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 7 minutes by foot from ...
Quality Inn
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The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.