Book Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Opens in a new windowPeace and quiet on the lake
Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
The price is AU$442 per night from 25 May to 26 May
AU$442
25 May - 26 May
includes taxes & fees
Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic ...
Opens in a new windowCozy Riverside Berkshires Retreat
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA
With a stay at this vacation home in Lanesborough, you'll be within a 10-minute drive of Crane Museum of Papermaking and Barrington Stage Company.
Opens in a new windowCozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Austerlitz NY
Located in Hillsdale, this vacation home is in the mountains, within a 15-minute drive of Hillsdale Town Hall and Ebenezer II Gifts and Antiques.
Opens in a new windowRenovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham NY
The price is AU$445 per night from 14 May to 15 May
AU$445
14 May - 15 May
includes taxes & fees
Located in Chatham, this vacation home is a 5-minute drive from The Mac-Haydn Theatre and 8 minutes from Hudson Chatham Winery.
Opens in a new windowPet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

East Chatham NY
Located in East Chatham, this vacation home is in the mountains, within a 15-minute drive of Queechy Lake and The Mac-Haydn Theatre.
Opens in a new windowSecluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire MA
When you stay at this vacation home in Cheshire, you'll be in the mountains, within a 5-minute drive of St Mary's of the Assumption Church and Mount Greylock ...
Opens in a new window19th c. Barn in the Berkshires
Beautiful Estate: Week of  8/30 still open to enjoy pool, pond, trails & more!

Beautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!

Old Chatham NY
Located in Old Chatham, this vacation home is on a lake, within a 10-minute drive of Shaker Museum and Library and Valatie Free Library.
Opens in a new windowBeautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

New Lebanon NY
The price is AU$541 per night from 14 May to 15 May
AU$541
14 May - 15 May
includes taxes & fees
When you stay at this vacation home in New Lebanon, you'll be in the mountains, within a 10-minute walk of New Lebanon Town Hall and Shatford Memorial Park.
Opens in a new windowNear Tanglewood: Historic Summer Retreat
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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
433 Holiday Homes
Lowest Price
AU$154
Highest Price
AU$541
Popular accommodation
Peace and quiet on the lake, Cozy Riverside Berkshires Retreat, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires! , Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight., Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay, 19th c. Barn in the Berkshires, Beautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!, Near Tanglewood: Historic Summer Retreat

Top trending hotels in Stockbridge

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is AU$303 per night from 18 May to 19 May
AU$303
18 May - 19 May
includes taxes & fees
With a stay at The Red Lion Inn in Stockbridge, you'll be next to a golf course, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Opens in a new windowThe Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
The price is AU$517 per night from 27 May to 28 May
AU$517
27 May - 28 May
includes taxes & fees
When you stay at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood in Stockbridge, you'll be next to a golf course, within a ...
Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AU$166 per night from 24 May to 25 May
AU$166
24 May - 25 May
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Opens in a new windowBerkshire Mountain Lodge
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Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is AU$154 per night from 25 May to 26 May
AU$154
25 May - 26 May
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Opens in a new windowBerkshires Untold
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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.