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

Amit

HK$4,281 total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

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

Stephentown

Robert B.

HK$4,692 total

includes taxes & fees

26 Oct - 27 Oct

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

3. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

HK$9,011 total

includes taxes & fees

27 Oct - 28 Oct

A wooden deck with a table and chairs, surrounded by a white railing.

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

Pittsfield

Stephen L.

HK$3,890 total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

New Lebanon

Joanna P.

HK$1,631 total

includes taxes & fees

27 Oct - 28 Oct

A spacious living room with a dining area, a kitchen, and a large window.

6. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

HK$1,766 total

includes taxes & fees

5 Nov - 6 Nov

A wooden kitchen with a central island, bar stools, and a dining table with chairs.

7. Cozy Home in Pownal VT

Pownal

Jeri R.

HK$1,608 total

includes taxes & fees

26 Oct - 27 Oct

A white two-story house with a porch, surrounded by trees and a hill.

8. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

HK$4,984 total

includes taxes & fees

24 Nov - 25 Nov

A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

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

Williamstown

Michelle B.

HK$4,853 total

includes taxes & fees

26 Oct - 27 Oct

A kitchen with white cabinets, a wooden dining table, and pendant lights.

10. A roomy remodeled retreat close to MassMoCA

North Adams

Diane

HK$3,776 total

includes taxes & fees

30 Oct - 31 Oct

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

11. Greylock Cabin

Florida

Margaret M.

HK$3,606 total

includes taxes & fees

22 Nov - 23 Nov

A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery.

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

West Sand Lake

Lauren C.

HK$4,213 total

includes taxes & fees

4 Nov - 5 Nov

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

13. Ellie’s Overlook, best view in the Berkshires!

Richmond

HK$5,420 total

includes taxes & fees

11 Nov - 12 Nov

A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

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

New Lebanon

Anonymous traveller

HK$4,503 total

includes taxes & fees

27 Oct - 28 Oct

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

15. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

HK$5,449 total

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a sofa, armchair, coffee table, and TV.

16. Spacious Central Berkshires Home for Groups

Lee

neil s.

HK$4,709 total

includes taxes & fees

1 Nov - 2 Nov

A living room with a sofa, armchairs, a coffee table, and a television.

17. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

HK$4,982 total

includes taxes & fees

26 Oct - 27 Oct

A cozy living room with a sofa, a fireplace, and large windows.

18. Luxury Barn Near Hudson With New Private Sauna

East Chatham

Michael T.

HK$5,327 total

includes taxes & fees

27 Oct - 28 Oct

A cozy living room with a fireplace, red and striped furniture, and large windows offering a view of greenery.

19. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Richmond

HK$9,893 total

includes taxes & fees

26 Oct - 27 Oct

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Top Hancock Hotel Reviews

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

8/10 Good

"all good"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Property is on a little lake and we had a balcony room with view of the lake. I can imagine it must be great to have in the warmer months, but we enjoyed the view nonetheless. Everything was clean, staff was friendly, the restaurant food we sampled was very good, the jet tub was much appreciated, and the location was perfect for exploring all of the quaint towns in the Berkshires. The nightly rate was very reasonable."

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