Book Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA
The price is NZ$511 per night from 18 Dec to 19 Dec
NZ$511
18 Dec - 19 Dec
includes taxes & fees
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Monument Mountain Reservation and Art et ...
Opens in a new windowPet Friendly Riverfront Home in Great Barrington
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge MA
Stay at this family-friendly holiday home in West Stockbridge. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Stockbridge Bowl and Berkshire ...
Opens in a new windowLocation!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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
Stay at this holiday home in Lanesborough. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
Opens in a new windowCozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
Stay at this holiday home in Becket. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
Opens in a new windowPeace and quiet on the lake
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield MA
Stay at this family-friendly holiday home in Pittsfield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and ...
Opens in a new windowBeautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Wildlife Lakeside Cottage
beautiful views, amazing wildlife, great location

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Lanesborough MA
Stay at this holiday home in Lanesborough. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
Opens in a new windowWildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee MA
Stay at this holiday home in Lee. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Greenock Country Club and Lee Library are located ...
Opens in a new windowCordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Berkshire House Stay

Berkshire House Stay

Lee MA
Stay at this holiday home in Lee. Enjoy laundry facilities, an in-room coffee maker and in-room fireplaces. Popular attractions Greenock Country Club and Lee ...
Opens in a new windowBerkshire House Stay
Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Copake Falls NY
Stay at this holiday home in Copake Falls. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions Copake Town Park and Bash Bish ...
Opens in a new windowFalls Reach In The Heart of Copake
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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
419 Holiday Homes
Lowest Price
NZ$182
Highest Price
NZ$798
Popular accommodation
Pet Friendly Riverfront Home in Great Barrington, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Peace and quiet on the lake, Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Berkshire House Stay, Falls Reach In The Heart of Copake

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 NZ$367 per night from 14 Jan to 15 Jan
NZ$367
14 Jan - 15 Jan 2026
includes taxes & fees
Stay at this historic hotel in Stockbridge. Enjoy free Wi-Fi, 3 restaurants and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
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 NZ$798 per night from 14 Jan to 15 Jan
NZ$798
14 Jan - 15 Jan 2026
includes taxes & fees
Stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Chesterwood and Norman Rockwell Museum are located ...
Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is NZ$220 per night from 18 Dec to 19 Dec
NZ$220
18 Dec - 19 Dec
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
Opens in a new windowVacation Village in the Berkshires
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 20 Dec to 21 Dec
NZ$182
20 Dec - 21 Dec
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
Don't see what you're looking for?
See all available properties in Stockbridge
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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.