Lenox Holiday Homes from £161: Search Holiday Homes in Lenox

A town hall with a central dome and columns, surrounded by trees and people.

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Lenox holiday homes

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

1. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

includes taxes & fees

14 Oct - 15 Oct

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

2. Spacious Central Berkshires Home for Groups

Lee

Beth S.

includes taxes & fees

14 Oct - 15 Oct

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

3. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

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.

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

Richmond

includes taxes & fees

18 Oct - 19 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.

includes taxes & fees

14 Oct - 15 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.

includes taxes & fees

2 Nov - 3 Nov

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

7. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

includes taxes & fees

20 Oct - 21 Oct

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

8. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

includes taxes & fees

26 Oct - 27 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.

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

Sherwood Forest

Sharon K.

includes taxes & fees

14 Oct - 15 Oct

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

10. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

includes taxes & fees

14 Oct - 15 Oct

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

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

Housatonic

Peter S.

includes taxes & fees

18 Oct - 19 Oct

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

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

Sherwood Forest

William C B.

includes taxes & fees

3 Nov - 4 Nov

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

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

Sherwood Forest

Frank M.

includes taxes & fees

28 Oct - 29 Oct

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

14. Home in Great Barrington

Great Barrington

Janet G.

includes taxes & fees

26 Oct - 27 Oct

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

15. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

includes taxes & fees

9 Nov - 10 Nov