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$1,671 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$1,750 total

includes taxes & fees

16 Nov - 17 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$3,651 total

includes taxes & fees

18 Nov - 19 Nov

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$4,506 total

includes taxes & fees

27 Oct - 28 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$4,399 total

includes taxes & fees

25 Oct - 26 Oct

6. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

HK$4,275 total

includes taxes & fees

23 Oct - 24 Oct

A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

7. Mayas Shangrila

Richmond

HK$9,144 total

includes taxes & fees

23 Oct - 24 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.

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

Richmond

HK$5,424 total

includes taxes & fees

25 Oct - 26 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$2,681 total

includes taxes & fees

25 Oct - 26 Oct

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

10. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

HK$3,867 total

includes taxes & fees

25 Oct - 26 Oct

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

11. Luxury Barn Near Hudson With New Private Sauna

East Chatham

Michael T.

HK$5,331 total

includes taxes & fees

27 Oct - 28 Oct

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

12. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

HK$9,018 total

includes taxes & fees

28 Oct - 29 Oct

A cozy living room with a wooden floor, a red armchair, a patterned sofa, and a glass door leading outside.

13. Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires

Richmond

HK$9,854 total

includes taxes & fees

18 Nov - 19 Nov

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

14. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

HK$5,145 total

includes taxes & fees

22 Oct - 23 Oct

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

15. All the comforts of home

Hudson

Lori M.

HK$1,109 total

includes taxes & fees

2 Nov - 3 Nov

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

16. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

HK$4,985 total

includes taxes & fees

26 Oct - 27 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 modern living room with a sofa, armchair, coffee table, and TV.

18. Spacious Central Berkshires Home for Groups

Lee

neil s.

HK$4,703 total

includes taxes & fees

1 Nov - 2 Nov

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

19. Cozy Home in Pownal VT

Pownal

Jeri R.

HK$1,609 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

Peter S.

HK$2,753 total

includes taxes & fees

29 Oct - 30 Oct

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Top New Lebanon Hotel Reviews

Hotel On North

10/10 Excellent

"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Hotel Downstream in North Adams was a great location for our overnight get-away to bike the Ashuwillticook Rail Trail. The hotel is right down-town, so we were able to walk to Public for dinner and to Bright Ideas Brewery afterwards, and to Dino's for breakfast in the morning. The room was very large and clean. We had a nice view of downtown and the mountains. Staff was very friendly -- we had a very quick check-in and check-out. Parking is right there and free. All very convenient. The hotel only serves continental breakfast, so we chose to go out, but it's nice that they provide water, coffee, tea and fruit all day long."

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