Lenox Vacation Homes

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

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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.

HK$4,977 total

includes taxes & fees

16 Oct - 17 Oct

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

2. Spacious Central Berkshires Home for Groups

Lee

Beth S.

HK$4,712 total

includes taxes & fees

19 Oct - 20 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.

HK$6,851 total

includes taxes & fees

18 Oct - 19 Oct

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

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

New Lebanon

Joanna P.

HK$1,615 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.

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

Richmond

HK$5,424 total

includes taxes & fees

25 Oct - 26 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$1,808 total

includes taxes & fees

5 Nov - 6 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.

HK$5,068 total

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.

HK$2,213 total

includes taxes & fees

26 Oct - 27 Oct

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

9. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

HK$3,786 total

includes taxes & fees

18 Oct - 19 Oct

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

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

Housatonic

Peter S.

HK$2,753 total

includes taxes & fees

29 Oct - 30 Oct

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

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

Sherwood Forest

William C B.

HK$2,490 total

includes taxes & fees

3 Nov - 4 Nov

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.

12. 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 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.

HK$3,087 total

includes taxes & fees

29 Oct - 30 Oct

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

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

15. Home in Great Barrington

Great Barrington

Janet G.

HK$2,809 total

includes taxes & fees

27 Oct - 28 Oct

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

16. 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.

HK$4,421 total

includes taxes & fees

9 Nov - 10 Nov

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

17. 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

18. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

HK$4,275 total

includes taxes & fees

19 Oct - 20 Oct

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

19. 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 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 Lenox Hotel Reviews

Howard Johnson by Wyndham Lenox

8/10 Good

"Clean, parking, room all good. Staff was very welcome and helpful."

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf."

Vacation Village in the Berkshires

10/10 Excellent

"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"

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