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Featured Holiday Homes in Hancock

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!
Mid Century Modern  4 bedroom home with sweeping mountain views in Williamstown

Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown

Williamstown MA
Located in Williamstown, this vacation home is a 2-minute drive from Green Mountain National Forest and 7 minutes from Farm Museum.
Opens in a new windowMid Century Modern 4 bedroom home with sweeping mountain views in Williamstown
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire MA
When you stay at this vacation home in Cheshire, you'll be in the mountains, within a 5-minute drive of St Mary's of the Assumption Church and Mount Greylock ...
Opens in a new window19th c. Barn in the Berkshires
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Beautiful Estate: Week of  8/30 still open to enjoy pool, pond, trails & more!

Beautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!

Old Chatham NY
Located in Old Chatham, this vacation home is on a lake, within a 10-minute drive of Shaker Museum and Library and Valatie Free Library.
Opens in a new windowBeautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!
Charming Berkshire Retreat-Minutes to Williamstown

Charming Berkshire Retreat-Minutes to Williamstown

Williamstown MA
With a stay at this vacation home in Williamstown, you'll be within a 5-minute walk of Mount Greylock State Reservation and Green River Wildlife Management ...
Opens in a new windowCharming Berkshire Retreat-Minutes to Williamstown
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome

3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome

Williamstown MA
A stay at this vacation home places you in the heart of Williamstown, steps from Lower Linear Park and 3 minutes by foot from Williams College.
Opens in a new window3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

East Chatham NY
Located in East Chatham, this vacation home is within a 15-minute drive of Queechy Lake and New Lebanon Library.
Opens in a new window120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown MA
Located in Williamstown, this vacation home is within a 5-minute drive of Williams College Taconic Golf Course and Williams College.
Opens in a new windowContemporary Berkshire Home with Views of Taconic Golf Course
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

East Chatham NY
Located in East Chatham, this vacation home is in the mountains, within a 15-minute drive of Queechy Lake and The Mac-Haydn Theatre.
Opens in a new windowSecluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
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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
262 Holiday Homes
Lowest Price
AU$165
Highest Price
AU$508
Popular accommodation
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown, 19th c. Barn in the Berkshires, Beautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!, Charming Berkshire Retreat-Minutes to Williamstown, 3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome, 120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views, Contemporary Berkshire Home with Views of Taconic Golf Course, Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

Top trending hotels in Hancock

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd Hancock MA
Fully refundableReserve now, pay when you stay
The price is AU$207 per night from 16 May to 17 May
AU$207
16 May - 17 May
includes taxes & fees
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 ...
Opens in a new windowJiminy Peak Mountain Resort
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock MA
The price is AU$508 per night from 19 May to 20 May
AU$508
19 May - 20 May
includes taxes & fees
A stay at this condo places you in the heart of Hancock, steps from Jiminy Peak Mountain Resort and Mountain Coaster.
Opens in a new window2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 24 May to 25 May
AU$166
24 May - 25 May
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Opens in a new windowBerkshire Mountain Lodge
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Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$165 per night from 19 May to 20 May
AU$165
19 May - 20 May
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Opens in a new windowBerkshires Untold
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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.