A calm lake surrounded by dense evergreen trees and a few deciduous trees with autumn leaves.

Holiday Homes in East Chatham

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for East Chatham holiday homes

A spacious room with a wooden ceiling, large windows, and a chandelier.

1. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
Luxury Barn Retreat — All-Season Escape Awaits!
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is NZ$362
includes taxes & fees
27 Sept - 28 Sept
NEW RENO - Chalet-style farm loft near Tanglewood
A modern building with a wooden deck and a door.

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

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is NZ$1,010
includes taxes & fees
28 Sept - 29 Sept
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A camping setup with a metal chair and a table by a river in a forest.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is NZ$590
includes taxes & fees
1 Oct - 2 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A spacious living room with a dining area, a kitchen, and a large window.

5. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is NZ$407
includes taxes & fees
28 Sept - 29 Sept
1800s Carriage house in Berkshires / Hudson Valley
A white two-story house with a porch, surrounded by trees and a hill.

6. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is NZ$801
includes taxes & fees
5 Oct - 6 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

7. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is NZ$991
includes taxes & fees
26 Sept - 27 Sept
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A wooden deck with a staircase leading to a covered porch area.

8. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is NZ$249
includes taxes & fees
5 Oct - 6 Oct
All the comforts of home
A bedroom with a bed, bedside lamp, and a window with curtains.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is NZ$1,206
includes taxes & fees
29 Sept - 30 Sept
Ellie’s Overlook, best view in the Berkshires!
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

10. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is NZ$556
includes taxes & fees
29 Sept - 30 Sept
Riverside Retreat in the Berkshires
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

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

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is NZ$954
includes taxes & fees
29 Sept - 30 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is NZ$590
includes taxes & fees
25 Oct - 26 Oct
Home in Great Barrington
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is NZ$608
includes taxes & fees
11 Oct - 12 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

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

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is NZ$674
includes taxes & fees
30 Sept - 1 Oct
Treat yourself at the stunning June Farms Wellness Huts!
A spacious room with a large window overlooking a lake, furnished with a sofa, chairs, and a table.

15. Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit

Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit
Averill Park
The price is NZ$1,255
includes taxes & fees
27 Sept - 28 Sept
Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit
A couple in a hot tub with a natural landscape in the background.

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

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "
United States
Jeffrey D.
The price is NZ$588
includes taxes & fees
20 Oct - 21 Oct
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

17. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is NZ$926
includes taxes & fees
2 Oct - 3 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A kitchen with white cabinets, a stove, a sink, and a television.

18. Tranquil 2-bedroom townhome with AC in charming Troy

Tranquil 2-bedroom townhome with AC in charming Troy
Troy
The price is NZ$430
includes taxes & fees
27 Sept - 28 Sept
Tranquil 2-bedroom townhome with AC in charming Troy
A modern kitchen with a central island, a dining area with a table and chairs, and a hallway leading to another room.

19. Perfect 4-bedroom house with AC in tranquil Albany

Perfect 4-bedroom house with AC in tranquil Albany
Delaware Avenue
10.0 out of 10, Exceptional, (3 reviews)
"The place so clean and beautiful we enjoyed the game refreshed my boy time memories and space and rooms so unique. I will definitely recommend that place then hotel. It’s more than five stars hotel."
United States
Alex
The price is NZ$966
includes taxes & fees
27 Sept - 28 Sept
Perfect 4-bedroom house with AC in tranquil Albany
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

20. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is NZ$1,328
includes taxes & fees
28 Sept - 29 Sept
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top East Chatham Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"The hotel was nice & clean, the staff were very kind & helpful. Will be returning again & def recommend!"
Glen 1-night trip
Posted 12 hours ago
Comfort Inn & Suites East Greenbush - Albany

Find out more about East Chatham

East Chatham Holiday Homes information

Number of reviews
192
Accommodation
485 Holiday Homes
Lowest Price
NZ$249
Highest Price
NZ$1,328