Book Holiday Homes in West Stockbridge

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Featured Holiday Homes in West Stockbridge

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$352 per night from 5 May to 6 May
AU$352
includes taxes & fees
5 May - 6 May
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock
The price is AU$1,645 per night from 28 Apr to 29 Apr
AU$1,645
includes taxes & fees
28 Apr - 29 Apr
Located in Pittsfield, this vacation home is on the waterfront, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Hancock Village Inn at Jiminy Peak
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

East Otis
With a stay at this vacation home in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from County Beach.
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
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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.
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
Lakeside Retreat Just You, The Lake & The View!

Lakeside Retreat Just You, The Lake & The View!

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.
Lakeside Retreat Just You, The Lake & The View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville
With a stay at this vacation home in Copake Lake, you'll be within a 5-minute drive of Copake Lake and Mosquito Island.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Athens
With a stay at this vacation home in Athens, you'll be on the waterfront, just a 1-minute walk from Sleepy Hollow Lake and 13 minutes by foot from Hudson ...
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Secluded Lux Mansion Pool Home with Amazing Views

Secluded Lux Mansion Pool Home with Amazing Views

Nassau
Located in Nassau, this vacation home is on a lake, within a 10-minute drive of Brookview Station Winery and Berkshire Retreat Center.
Secluded Lux Mansion Pool Home with Amazing Views
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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
521 Holiday Homes
Lowest Price
AU$110
Highest Price
AU$1,645
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Hancock Village Inn at Jiminy Peak, 4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, Spectacular views and close to Great Barrington., Peace and quiet on the lake, Lakeside Retreat Just You, The Lake & The View!, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!, Secluded Lux Mansion Pool Home with Amazing Views

Top trending hotels in West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
The price is AU$110 per night from 29 Apr to 30 Apr
AU$110
includes taxes & fees
29 Apr - 30 Apr
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 ...
Pleasant Valley Motel West Stockbridge
Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street, West Stockbridge, MA
The price is AU$250 per night from 29 Apr to 30 Apr
AU$250
includes taxes & fees
29 Apr - 30 Apr
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.
Shaker Mill Inn
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$201 per night from 8 May to 9 May
AU$201
includes taxes & fees
8 May - 9 May
With a stay at Berkshires Untold in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House Berkshires
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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is AU$210 per night from 14 May to 15 May
AU$210
includes taxes & fees
14 May - 15 May
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.