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 NZ$386 per night from 18 Apr to 19 Apr
NZ$386
includes taxes & fees
18 Apr - 19 Apr
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Crane ...
Berkshire Village Carriage House - Super Private!!
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock
The price is NZ$2,138 per night from 1 May to 2 May
NZ$2,138
includes taxes & fees
1 May - 2 May
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy a pool table, in-room washers/dryers, and an in-room coffeemaker. Popular attractions ...
Hancock Village Inn at Jiminy Peak
Secluded Lux Mansion Pool Home with Amazing Views

Secluded Lux Mansion Pool Home with Amazing Views

Nassau
Book a stay at this family-friendly vacation home in Nassau. Enjoy private pools, a fitness center, and a garden. Popular attractions Brookview Station Winery ...
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
Stay at this vacation home in Lenox. Enjoy free WiFi, a garden, and in-room washers/dryers. Popular attractions Tanglewood Music Center and The Bookstore are ...
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
Book a stay at this family-friendly vacation home in Richmond. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Tanglewood Music Center and ...
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Mountain Blossom Retreat by Evergreen Home

Mountain Blossom Retreat by Evergreen Home

Lanesborough
Stay at this vacation home in Lanesborough. Enjoy private pools, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mount Greylock ...
Mountain Blossom Retreat by Evergreen Home
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

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

Lee
Stay at this vacation home in Lee. Enjoy free WiFi, a garden, and patios. Popular attractions Tanglewood Music Center and Greenock Country Club are located ...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

New Lebanon
The price is NZ$571 per night from 6 Apr to 7 Apr
NZ$571
includes taxes & fees
6 Apr - 7 Apr
Stay at this vacation home in New Lebanon. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Shatford Memorial Park and New Lebanon Library ...
Near Tanglewood: Historic Summer Retreat
Wellspring by AvantStay | Indoor Pool + Views

Wellspring by AvantStay | Indoor Pool + Views

West Stockbridge
Book a stay at this family-friendly vacation home in West Stockbridge. Enjoy free WiFi, private pools, and a sauna. Popular attractions Tanglewood Music Center ...
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
270 Holiday Homes
Lowest Price
NZ$187
Highest Price
NZ$2,138
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
Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition ...
Club Wyndham Bentley Brook
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
The price is NZ$254 per night from 5 May to 6 May
NZ$254
includes taxes & fees
5 May - 6 May
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 bars/lounges. Our guests praise the property condition in our reviews. Popular ...
Jiminy Peak Mountain Resort
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
The price is NZ$829 per night from 5 May to 6 May
NZ$829
includes taxes & fees
5 May - 6 May
Stay at this vacation home in Hancock. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
Comfortable Berkshires retreat on mtn resort, SISO
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$187 per night from 17 Apr to 18 Apr
NZ$187
includes taxes & fees
17 Apr - 18 Apr
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
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.

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