Pittsfield Vacation Homes

A historic building with classical architecture, a traffic light, and a yellow taxi.

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Our top choices for Pittsfield holiday homes

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

1. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

HK$3,867 total

includes taxes & fees

19 Oct - 20 Oct

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

2. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

HK$9,017 total

includes taxes & fees

20 Oct - 21 Oct

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

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

New Lebanon

Joanna P.

HK$1,615 total

includes taxes & fees

18 Oct - 19 Oct

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

4. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

HK$1,768 total

includes taxes & fees

9 Nov - 10 Nov

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

5. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Robert B.

HK$4,399 total

includes taxes & fees

18 Oct - 19 Oct

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

6. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

HK$3,786 total

includes taxes & fees

18 Oct - 19 Oct

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.

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

Richmond

HK$5,424 total

includes taxes & fees

25 Oct - 26 Oct

8. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

HK$4,249 total

includes taxes & fees

18 Oct - 19 Oct

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

9. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

HK$4,977 total

includes taxes & fees

16 Oct - 17 Oct

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

10. Spacious Central Berkshires Home for Groups

Lee

neil s.

HK$4,712 total

includes taxes & fees

19 Oct - 20 Oct

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

11. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

HK$5,068 total

includes taxes & fees

20 Oct - 21 Oct

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

12. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

13. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

HK$2,498 total

includes taxes & fees

3 Nov - 4 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$4,506 total

includes taxes & fees

27 Oct - 28 Oct

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

15. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

HK$2,944 total

includes taxes & fees

27 Oct - 28 Oct

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

16. Cozy Home in Pownal VT

Pownal

Jess M.

HK$1,609 total

includes taxes & fees

19 Oct - 20 Oct

A staircase with a wooden handrail and a white wall with a light switch.

17. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

HK$2,213 total

includes taxes & fees

26 Oct - 27 Oct

A hot tub with a string of lights above it, set against a dark night sky.

18. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

HK$3,087 total

includes taxes & fees

28 Oct - 29 Oct

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

19. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

HK$2,753 total

includes taxes & fees

26 Oct - 27 Oct

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

20. Luxury Barn Near Hudson With New Private Sauna

East Chatham

Michael T.

HK$5,331 total

includes taxes & fees

21 Oct - 22 Oct

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Top Pittsfield Hotel Reviews

FairBridge Inn Express

10/10 Excellent

"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"

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