Hancock Vacation Homes

A road lined with autumn-colored trees, a green house, and a mountain in the background.

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Our top choices for Hancock holiday homes

1. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Maura L.

HK$4,244 total

includes taxes & fees

9 Sept - 10 Sept

2. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Diego G.

HK$4,394 total

includes taxes & fees

9 Sept - 10 Sept

3. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

HK$8,487 total

includes taxes & fees

9 Sept - 10 Sept

4. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Ann C.

HK$4,309 total

includes taxes & fees

15 Sept - 16 Sept

5. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Varun M.

HK$1,631 total

includes taxes & fees

10 Sept - 11 Sept

6. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

HK$1,757 total

includes taxes & fees

9 Sept - 10 Sept

7. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

HK$3,705 total

includes taxes & fees

9 Sept - 10 Sept

8. Cozy Home in Pownal VT

Pownal

Jess M.

HK$1,511 total

includes taxes & fees

13 Sept - 14 Sept

9. North Getaway Cottage

Williamstown

Carole S.

HK$3,498 total

includes taxes & fees

17 Sept - 18 Sept

10. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Williamstown

Michelle B.

HK$4,681 total

includes taxes & fees

9 Sept - 10 Sept

11. A roomy remodeled retreat close to MassMoCA

North Adams

Jennifer O.

HK$3,774 total

includes taxes & fees

9 Sept - 10 Sept

12. NEW RENO Historic Creamery in Berkshires w/hot tub

New Lebanon

Anonymous traveller

HK$4,175 total

includes taxes & fees

14 Sept - 15 Sept

13. The Greylock Cabin

Florida

Margaret M.

HK$3,902 total

includes taxes & fees

7 Oct - 8 Oct

14. Luxury Barn Retreat — All-Season Escape Awaits!

East Chatham

Michael T.

HK$4,882 total

includes taxes & fees

15 Sept - 16 Sept

15. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

HK$4,557 total

includes taxes & fees

13 Sept - 14 Sept

16. Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

SteveS

HK$3,879 total

includes taxes & fees

14 Sept - 15 Sept

17. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveller

HK$6,708 total

includes taxes & fees

30 Sept - 1 Oct

18. June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often

West Sand Lake

LauraS

HK$4,375 total

includes taxes & fees

14 Sept - 15 Sept

19. Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

Lauren C.

HK$4,375 total

includes taxes & fees

23 Sept - 24 Sept

20. WOW! A spectacular Hobbit House in the forest at June Farms!

West Sand Lake

Anonymous traveller

HK$4,891 total

includes taxes & fees

16 Sept - 17 Sept

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Top Hancock Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Very clean room the staff were very pleasant. The breakfast was pretty decent. The only issue we had was parking that didn’t seem to be enough spots for the hotel when we came back from a concert at Tanglewood. Every spot at the hotel was taken. Luckily somebody left otherwise the place was great."

Jiminy Peak Mountain Resort

10/10 Excellent

"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"

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