New Lebanon Vacation Homes

A marshland with tall grasses and a forested hill in the background under a partly cloudy sky.

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Our top choices for New Lebanon holiday homes

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

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

New Lebanon

Joanna P.

HK$1,614 total

includes taxes & fees

28 Oct - 29 Oct

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

2. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

HK$1,767 total

includes taxes & fees

5 Nov - 6 Nov

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

3. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

HK$3,348 total

includes taxes & fees

28 Oct - 29 Oct

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

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

New Lebanon

Anonymous traveller

HK$4,501 total

includes taxes & fees

28 Oct - 29 Oct

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$4,668 total

includes taxes & fees

28 Oct - 29 Oct

6. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

HK$4,246 total

includes taxes & fees

28 Oct - 29 Oct

A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

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

Richmond

"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...

Delaney M.

HK$5,420 total

includes taxes & fees

11 Nov - 12 Nov

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

8. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

HK$3,864 total

includes taxes & fees

28 Oct - 29 Oct

A camping setup with a metal chair and a table by a river in a forest.

9. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

Jess S.

HK$2,680 total

includes taxes & fees

28 Oct - 29 Oct

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

10. Luxury Barn Near Hudson With New Private Sauna

East Chatham

Michael T.

HK$5,329 total

includes taxes & fees

28 Oct - 29 Oct

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

11. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

HK$9,014 total

includes taxes & fees

28 Oct - 29 Oct

A modern building with a wooden deck and a door.

12. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

HK$5,492 total

includes taxes & fees

28 Oct - 29 Oct

A wooden deck with a staircase leading to a covered porch area.

13. All the comforts of home

Hudson

Lori M.

HK$1,109 total

includes taxes & fees

1 Nov - 2 Nov

A room with a large window, two sofas, and a small table.

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

Richmond

HK$9,881 total

includes taxes & fees

28 Oct - 29 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$5,066 total

includes taxes & fees

2 Nov - 3 Nov

A dining area with a wooden table, chairs, and a ceiling fan.

16. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

HK$2,213 total

includes taxes & fees

28 Oct - 29 Oct

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

17. Cozy Home in Pownal VT

Pownal

Jeri R.

HK$1,600 total

includes taxes & fees

28 Oct - 29 Oct

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

18. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

HK$4,947 total

includes taxes & fees

28 Oct - 29 Oct

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

19. Spacious Central Berkshires Home for Groups

Lee

neil s.

HK$4,675 total

includes taxes & fees

1 Nov - 2 Nov

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

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

Housatonic

Eric H.

HK$2,733 total

includes taxes & fees

28 Oct - 29 Oct

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Top New Lebanon Hotel Reviews

The Yankee Inn

8/10 Good

"I enjoyed this hotel, mostly. Our room had a lovely heat generating gas fireplace. And having a private outside balcony to sit on was wonderful. My only gripe was the poor quality of the included free breakfast, and coffee! We skipped it entirely on our last morning there. But it looked like many people enjoyed it."

Berkshire Mountain Lodge

8/10 Good

"I love having a separate bedroom and a kitchen to make coffee in the morning. This is not my first time staying there, and every time the beds were uncomfortable. When you look at the bed, and there are 2 curves to the mattress where they have been slept in over time, you know it's going to be a tough night. The pillows were old as well. This is a typical timeshare where upgrades to furniture are few and far between. Other than that, it is a value for your money. And very convenient if you are a skier."

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