Book Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

Spacious Home nestled along the Blackberry River in Northwest CT

Spacious Home nestled along the Blackberry River in Northwest CT

East Canaan
When you stay at this vacation home in East Canaan, you'll be on a river, within a 5-minute drive of Beckley Furnace Industrial Park and Haystack Mountain State ...
Spacious Home nestled along the Blackberry River in Northwest CT
Peace and quiet on the lake

Peace and quiet on the lake

Becket
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.
Peace and quiet on the lake
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
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Berkshire Ashmere Lake lodging. Quiet  room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
With a stay at this vacation home in Hinsdale, you'll be within a 15-minute drive of Bas Ridge Golf Course and Crane Museum of Papermaking.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Deluxe Queen Room with 2 Queen Beds

Deluxe Queen Room with 2 Queen Beds

2 out of 5
Lee
The price is AU$207 per night from 1 Sept to 2 Sept
AU$207
1 Sept - 2 Sept
includes taxes & fees
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
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.
Taconic Hideaway – Swimming, BBQ Pit, Hiking

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2 out of 5
Copake
With a stay at this vacation home in Copake, you'll be within a 10-minute drive of Copake Town Hall and Callan Family Care.
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Copake Falls
Located in Copake Falls, this vacation home is in a rural location, within a 5-minute drive of Taconic State Park and Callan Family Care.
Falls Reach In The Heart of Copake
Poolside Luxe at Long Pond

Poolside Luxe at Long Pond

Great Barrington
Located in Great Barrington, Poolside Luxe at Long Pond is in a rural location, within a 10-minute drive of Monument Mountain and Housatonic River.
Poolside Luxe at Long Pond
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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
474 Holiday Homes
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

Top trending hotels in Stockbridge

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$386 per night from 18 Aug to 19 Aug
AU$386
18 Aug - 19 Aug
includes taxes & fees
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
Fully refundableReserve now, pay when you stay
The price is AU$412 per night from 12 Aug to 13 Aug
AU$412
12 Aug - 13 Aug
includes taxes & fees
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
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$728 per night from 25 Aug to 26 Aug
AU$728
25 Aug - 26 Aug
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 ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Save an average of 15% on thousands of hotels when you're signed in
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$202 per night from 27 Aug to 28 Aug
AU$202
27 Aug - 28 Aug
includes taxes & fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
Vacation Village in the Berkshires
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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.