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
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain ...
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
Stay at this vacation home in Pownal. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mountain Meadow Preserve Vermont Trailhead and Williamstown ...
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
Stay at this vacation home in Stockbridge. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Tanglewood Music Center and Berkshire Theatre ...
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 NZ$1,023 per night from 24 Sept to 25 Sept
NZ$1,023
24 Sept - 25 Sept
includes taxes & fees
Stay at this vacation home in Lee. Enjoy laundry facilities and in-room fireplaces. Popular attractions Tanglewood Music Center and Berkshire Mountain Country ...
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
Book a stay at this family-friendly vacation home in Lenox. Enjoy private pools, laundry facilities, and in-room jetted tubs. Popular attractions Tanglewood ...
Opens in a new windowAmore Estate - beautiful room with many places to explore and relax in.
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Cummington
Stay at this vacation home in Cummington. Enjoy a garden, laundry facilities, and patios.
Opens in a new windowBeautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown
Stay at this vacation home in Williamstown. Enjoy a garden, laundry facilities, and patios. Popular attractions Williams College Taconic Golf Course and Lunder ...
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
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
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
Stay at this vacation home in Berkshire County. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and National ...
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
288 Holiday Homes
Lowest Price
NZ$280
Highest Price
NZ$1,023
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., Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, 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 NZ$280 per night from 19 Oct to 20 Oct
NZ$280
19 Oct - 20 Oct
includes taxes & fees
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ...
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
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 ...
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 NZ$791 per night from 21 Sept to 22 Sept
NZ$791
21 Sept - 22 Sept
includes taxes & fees
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 ...
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 NZ$554 per night from 1 Oct to 2 Oct
NZ$554
1 Oct - 2 Oct
includes taxes & fees
Stay at this condo in Hancock. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
Opens in a new window2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Don't see what you're looking for?
See all available properties in Hancock
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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.