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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Old Chatham vacation homes

Coffee/tea maker, fridge, microwave, oven

1. 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 ￥10,938
￥32,502 total
includes taxes & fees
Sep 10 - Sep 11
NEW RENO - Chalet-style farm loft near Tanglewood
Exterior detail

2. 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 ￥56,097
￥115,157 total
includes taxes & fees
Sep 8 - Sep 9
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Property grounds

3. 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, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
The price is ￥31,252
￥53,378 total
includes taxes & fees
Sep 20 - Sep 21
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
TV, DVD player, books, video library

4. 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 ￥13,282
￥35,021 total
includes taxes & fees
Sep 9 - Sep 10
1800s Carriage house in Berkshires / Hudson Valley
Exterior

5. 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 ￥34,533
￥77,498 total
includes taxes & fees
Sep 9 - Sep 10
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Coffee/tea maker, fridge, microwave, stovetop

6. 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 ￥27,502
￥88,286 total
includes taxes & fees
Sep 8 - Sep 9
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Property grounds

7. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,595
￥22,088 total
includes taxes & fees
Sep 10 - Sep 11
All the comforts of home
Outdoor dining

8. 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 traveler
The price is ￥37,815
￥82,693 total
includes taxes & fees
Sep 14 - Sep 15
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

9. 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 ￥45,436
￥77,318 total
includes taxes & fees
Sep 14 - Sep 15
Treat yourself at the stunning June Farms Wellness Huts!
Interior

10. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is ￥31,643
￥49,483 total
includes taxes & fees
Sep 8 - Sep 9
Riverside Retreat in the Berkshires
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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 ￥27,346
￥49,919 total
includes taxes & fees
Sep 9 - Sep 10
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

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

Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
Pine Hills
9.8 out of 10, Exceptional, (7 reviews)
"This property is just as listed. Very clean, comfortable, pet, friendly, and comes with all necessities. From booking to check out, everything went extremely smooth!"
United States
Lisette T.
The price is ￥27,033
￥64,129 total
includes taxes & fees
Sep 8 - Sep 9
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
Interior

13. Albany Retreat- Free Breakfast & Parking Included

Albany Retreat- Free Breakfast & Parking Included
West End
5.8 out of 10, (8 reviews)
"Best stay yet"
United States
Jacob M.
The price is ￥8,438
￥20,926 total
includes taxes & fees
Sep 8 - Sep 9
Albany Retreat- Free Breakfast & Parking Included
Coffee/tea maker, fridge, microwave, oven

14. 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 ￥61,879
￥117,783 total
includes taxes & fees
Sep 8 - Sep 9
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Terrace/patio

15. “The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany

“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Pine Hills
9.6 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay at this property and will rent again when in the area. The owners were very responsive and great to work with. The apt was beautiful and immaculate. We enjoyed our stay very much. The only area that was perfect was the outside stairs to the front door— uneven, steep, etc. We had older guest with us and this was concerning. But we managed. Thanks again for a great stay"
United States
Melissa A.
The price is ￥27,986
￥68,026 total
includes taxes & fees
Sep 13 - Sep 14
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Property grounds

16. Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
The price is ￥39,534
￥82,524 total
includes taxes & fees
Sep 30 - Oct 1
Larkspire I Sleepy Hollow Lake I Beach & Firepit
Exterior detail

17. Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is ￥38,284
￥79,105 total
includes taxes & fees
Sep 30 - Oct 1
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Coffee/tea maker, fridge, microwave, oven

18. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥29,814
￥48,140 total
includes taxes & fees
Sep 8 - Sep 9
Home in Great Barrington
Outdoor dining

19. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very Good, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is ￥49,081
￥85,893 total
includes taxes & fees
Sep 8 - Sep 9
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

20. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ￥90,076
￥169,156 total
includes taxes & fees
Sep 9 - Sep 10
Hancock Village Inn Near Jiminy Peak
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 Old Chatham Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"This is a clean, well maintained property. Seemed pretty new. We did not try the pool. It is indoors, and a good size. The breakfast was among the best we’ve had in our travels (except unfortunately for the coffee). Very comfortable bed provides a good night’s sleep (the main thing). A very good place to stay."
Philip 1-night trip
Posted 3 hours ago
Comfort Inn & Suites East Greenbush - Albany

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Old Chatham Vacation Homes information

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