Book Holiday Homes in Hancock

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Featured Holiday Homes in Hancock

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
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
Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

Pownal
With a stay at this vacation home in Pownal, you'll be steps from Green Mountain National Forest and a 3-minute drive from Mountain Meadow Preserve.
Opens in a new windowBright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown
Stockbridge Village in Summer

Stockbridge Village in Summer

Stockbridge
With a stay at this vacation home in Stockbridge, you'll be on a river, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Opens in a new windowStockbridge Village in Summer
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Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
The price is AU$1,269 per night from 21 Oct to 22 Oct
AU$1,269
21 Oct - 22 Oct
includes taxes & fees
With a stay at this vacation home in Lee, you'll be within a 10-minute drive of Tanglewood Music Center and Housatonic River.
Opens in a new windowSpacious 5-bedroom house in charming Lee with WiFi
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
With a stay at this vacation home in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Wyndhurst Golf & Club.
Opens in a new windowAmore Estate - beautiful room with many places to explore and relax in.
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

Cummington
With a stay at this vacation home in Cummington, you'll be on the waterfront, and 8.1 mi (13 km) from Swift River and 8.3 mi (13.3 km) from Westfield River.
Opens in a new window3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown
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
Wildlife Lakeside Cottage
beautiful views, amazing wildlife, great location

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Lanesborough
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
General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge

4 out of 5
Stockbridge
This family-friendly vacation home is 5.4 mi (8.7 km) from Tanglewood Music Center and 1.5 mi (2.5 km) from Berkshire Theatre Festival.
Opens in a new windowGeneral Williams Estate House Lenox/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.

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
294 Holiday Homes
Lowest Price
AU$254
Highest Price
AU$1,269
Popular accommodation
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown, Stockbridge Village in Summer, Spacious 5-bedroom house in charming Lee with WiFi, Amore Estate - beautiful room with many places to explore and relax in., 3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest, Contemporary Berkshire Home with Views of Taconic Golf Course, Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location, General Williams Estate House Lenox/Stockbridge

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$254 per night from 19 Oct to 20 Oct
AU$254
19 Oct - 20 Oct
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
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 ...
Opens in a new windowClub Wyndham Bentley Brook
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
The price is AU$731 per night from 28 Sept to 29 Sept
AU$731
28 Sept - 29 Sept
includes taxes & fees
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.
Opens in a new windowComfortable Berkshires retreat on mtn resort, SISO
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2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock
The price is AU$522 per night from 28 Oct to 29 Oct
AU$522
28 Oct - 29 Oct
includes taxes & fees
With a stay at this condo, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Opens in a new window2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
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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.