Old Chatham Vacation Homes

A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

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Our top choices for Old Chatham 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

1 Nov - 2 Nov

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 modern building with a wooden deck and a door.

3. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

HK$5,193 total

includes taxes & fees

2 Nov - 3 Nov

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

Chatham

Jess S.

HK$2,680 total

includes taxes & fees

29 Oct - 30 Oct

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

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

Christine C.

HK$3,387 total

includes taxes & fees

1 Nov - 2 Nov

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

6. Luxury Barn Near Hudson With New Private Sauna

East Chatham

Michael T.

HK$5,329 total

includes taxes & fees

29 Oct - 30 Oct

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

7. All the comforts of home

Hudson

Lori M.

HK$1,109 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Stephentown

Robert B.

HK$4,667 total

includes taxes & fees

29 Oct - 30 Oct

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

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

New Lebanon

Anonymous traveller

HK$4,663 total

includes taxes & fees

9 Nov - 10 Nov

A lobby with a brown leather sofa set, a patterned carpet, and a chandelier.

10. Albany Retreat- Free Breakfast & Parking Included

West End

Jacob M.

HK$1,051 total

includes taxes & fees

1 Nov - 2 Nov

A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

11. Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

SteveS

HK$3,607 total

includes taxes & fees

3 Nov - 4 Nov

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

12. 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$5,422 total

includes taxes & fees

11 Nov - 12 Nov

A spacious room with wooden flooring, a black and white bench, a small table with a plant, and a door leading to an outdoor area.

13. Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Hudson

Jeffrey D.

HK$4,560 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with white cabinets, a wooden countertop, and a large TV mounted on the wall.

14. Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

Pine Hills

Mary R.

HK$3,067 total

includes taxes & fees

22 Nov - 23 Nov

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

15. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

HK$2,484 total

includes taxes & fees

2 Nov - 3 Nov

16. Classic Albany Charm – Fully Furnished

Center Square

A bedroom with two beds, a ceiling fan, a dresser, and a television.

17. Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

Albany

Anonymous traveller

HK$2,711 total

includes taxes & fees

22 Nov - 23 Nov

18. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

HK$4,247 total

includes taxes & fees

29 Oct - 30 Oct

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

19. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

HK$5,066 total

includes taxes & fees

2 Nov - 3 Nov

A living room with a fireplace, a television mounted above it, and a sofa.

20. Downtown 3BR duplex full kitchen parking off i-787

Arbor Hill

Francesca L.

HK$2,959 total

includes taxes & fees

2 Nov - 3 Nov

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Top Old Chatham Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"Clean and comfortable"

The Yankee Inn

8/10 Good

"We stayed at the Yankee Inn for 1 night. We had no problems with check-in. Our room was clean but outdated except the bathroom which was very nice. Good water pressure in the shower and the bed was comfortable. Unfortunately, due to myself not feeling well, we did not use the hot tub, enjoy the fire pit or try breakfast all of which would have likely improved our stay. Maybe next time!"

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