Book Holiday Homes in Hancock

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Featured Holiday Homes in Hancock

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$364 per night from 7 Apr to 8 Apr
AU$364
includes taxes & fees
7 Apr - 8 Apr
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$1,755 per night from 8 Apr to 9 Apr
AU$1,755
includes taxes & fees
8 Apr - 9 Apr
With a stay at this vacation home in Pittsfield, you'll be on the waterfront, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Hancock Village Inn at Jiminy Peak
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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Heart of Lenox Walk to Town Cozy Cottage!

Heart of Lenox Walk to Town Cozy Cottage!

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and The Bookstore.
Heart of Lenox Walk to Town Cozy Cottage!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Richmond
With a stay at this vacation home in Richmond, you'll be within a 10-minute drive of Tanglewood Music Center and Fairfield Brook WMA.
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Mountain Blossom Retreat by Evergreen Home

Mountain Blossom Retreat by Evergreen Home

Lanesborough
With a stay at this vacation home in Lanesborough, you'll be in the mountains, within a 15-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State ...
Mountain Blossom Retreat by Evergreen Home
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

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

Lee
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.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

New Lebanon
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.
Near Tanglewood: Historic Summer Retreat
Wellspring by AvantStay | Indoor Pool + Views

Wellspring by AvantStay | Indoor Pool + Views

West Stockbridge
With a stay at this vacation home in West Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Hotchkiss Mobile Studio.
Wellspring by AvantStay | Indoor Pool + 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.

Hancock 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 Hancock vacation homes are the perfect way for you to wing it.

Holiday houses in Hancock 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 Hancock 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 Hancock adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Hancock 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 Hancock 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.

Hancock Holiday Homes essential information

Accommodation
272 Holiday Homes
Lowest Price
AU$191
Highest Price
AU$1,755
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Hancock Village Inn at Jiminy Peak, Secluded Lux Mansion Pool Home with Amazing Views, Heart of Lenox Walk to Town Cozy Cottage!, Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!, Mountain Blossom Retreat by Evergreen Home, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Near Tanglewood: Historic Summer Retreat, Wellspring by AvantStay | Indoor Pool + Views

Top trending hotels in Hancock

Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
1 Corey Road, Hancock, MA
When you stay at Club Wyndham Bentley Brook in Hancock, you'll be in the mountains, just steps from Jiminy Peak Mountain Resort and a 3-minute drive from Mountain ...
Club Wyndham Bentley Brook
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
The price is AU$233 per night from 6 Apr to 7 Apr
AU$233
includes taxes & fees
6 Apr - 7 Apr
Located in Hancock, Jiminy Peak Mountain Resort is in the mountains, within a 15-minute drive of Mount Greylock State Reservation Visitor Center and Waubeeka ...
Jiminy Peak Mountain Resort
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
The price is AU$775 per night from 6 Apr to 7 Apr
AU$775
includes taxes & fees
6 Apr - 7 Apr
With a stay at this vacation home in Hancock, you'll be within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Comfortable Berkshires retreat on mtn resort, SISO
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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$191 per night from 6 Apr to 7 Apr
AU$191
includes taxes & fees
6 Apr - 7 Apr
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House 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.