Book Holiday Homes in West Stockbridge

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Featured Holiday Homes in West Stockbridge

Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA
The price is AU$449 per night from 4 Jan to 5 Jan
AU$449
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Great Barrington, this vacation home is on a river, a 4-minute walk from Monument Mountain Reservation and within a 5-minute drive of Housatonic ...
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
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.
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
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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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
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
Located in Pittsfield, this vacation home is on a lake, within a 5-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.
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
With a stay at this vacation home in Lanesborough, you'll be on a lake, within a 15-minute drive of Jiminy Peak Mountain Resort and St Mary's of the Assumption ...
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
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.
Opens in a new windowCordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Berkshire House Stay

Berkshire House Stay

Lee MA
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Opens in a new windowBerkshire House Stay
Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Copake Falls NY
When you stay at this vacation home in Copake Falls, you'll be in the mountains, within a 5-minute drive of Taconic State Park and Callan Family Care.
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.

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
480 Holiday Homes
Lowest Price
AU$85
Highest Price
AU$449
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 West Stockbridge

Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
The price is AU$191 per night from 30 Dec to 31 Dec
AU$191
30 Dec - 31 Dec
includes taxes & fees
With a stay at Shaker Mill Inn in West Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Ebenezer II Gifts and Antiques.
Opens in a new windowShaker Mill Inn
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd West Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is AU$85 per night from 1 Jan to 2 Jan
AU$85
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at Pleasant Valley Motel West Stockbridge in West Stockbridge, you'll be near the beach, within a 15-minute drive of Tanglewood Music Center and ...
Opens in a new windowPleasant Valley Motel West Stockbridge
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$190 per night from 25 Jan to 26 Jan
AU$190
25 Jan - 26 Jan 2026
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 ...
Opens in a new windowVacation Village in the Berkshires
Save an average of 15% on thousands of hotels when you're signed in
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
The price is AU$154 per night from 4 Jan to 5 Jan
AU$154
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Don't see what you're looking for?
See all available properties in West 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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.