Search Vacation Homes in Old Chatham
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Old Chatham vacation homes
1. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
Joanna P.
The price is AED 257
AED 719 total
includes taxes & fees
3 Nov - 4 Nov
2. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew 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)"
Leslie H.
The price is AED 312
AED 778 total
includes taxes & fees
5 Nov - 6 Nov
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!"
Terri E.
The price is AED 988
AED 2,189 total
includes taxes & fees
16 Nov - 17 Nov
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, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
Jess S.
The price is AED 735
AED 1,197 total
includes taxes & fees
3 Nov - 4 Nov
5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
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. "
Christine C.
The price is AED 617
AED 1,508 total
includes taxes & fees
3 Nov - 4 Nov
6. Luxury Barn Near Hudson With New Private Sauna
Luxury Barn Near Hudson With New Private SaunaEast Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
Michael T.
The price is AED 1,405
AED 2,289 total
includes taxes & fees
3 Nov - 4 Nov
7. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ DeckStephentown
9.2 out of 10, Wonderful, (10 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
Robert B.
The price is AED 746
AED 2,087 total
includes taxes & fees
3 Nov - 4 Nov
8. All the comforts of home
All the comforts of homeHudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
Lori M.
The price is AED 390
AED 486 total
includes taxes & fees
4 Nov - 5 Nov
9. NEW RENO Historic Creamery in Berkshires w/hot tub
NEW RENO Historic Creamery in Berkshires w/hot tubNew Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
Anonymous traveler
The price is AED 1,091
AED 2,084 total
includes taxes & fees
2 Dec - 3 Dec
10. Ellie’s Overlook, best view in the Berkshires!
Ellie’s Overlook, best view in the Berkshires!Richmond
10.0 out of 10, Exceptional, (1 review)
"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.
The price is AED 1,157
AED 2,393 total
includes taxes & fees
7 Nov - 8 Nov
11. Albany Retreat- Free Breakfast & Parking Included
Albany Retreat- Free Breakfast & Parking IncludedWest End
5.8 out of 10, (8 reviews)
"Best stay yet"
Jacob M.
The price is AED 202
AED 464 total
includes taxes & fees
4 Nov - 5 Nov
12. 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)
"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."
Lauren C.
The price is AED 952
AED 1,819 total
includes taxes & fees
3 Nov - 4 Nov
13. Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE ParkingPine Hills
9.8 out of 10, Exceptional, (8 reviews)
"Perfect accommodations. Every detail was provided!"
Mary R.
The price is AED 551
AED 1,325 total
includes taxes & fees
22 Nov - 23 Nov
14. 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 HudsonHudson
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "
Jeffrey D.
The price is AED 955
AED 2,040 total
includes taxes & fees
22 Nov - 23 Nov
15. 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)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
Eric H.
The price is AED 735
AED 1,219 total
includes taxes & fees
3 Nov - 4 Nov
16. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the BerkshiresRichmond
The price is AED 3,324
AED 4,634 total
includes taxes & fees
4 Nov - 5 Nov
17. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
Ofer C.
The price is AED 1,253
AED 2,257 total
includes taxes & fees
3 Nov - 4 Nov
18. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET FriendStottville
The price is AED 1,455
AED 2,641 total
includes taxes & fees
10 Nov - 11 Nov
19. Downtown 3BR duplex full kitchen parking off i-787
Downtown 3BR duplex full kitchen parking off i-787Arbor Hill
10.0 out of 10, Exceptional, (6 reviews)
"My group of 7 plus myself really enjoyed staying at this house. Ideal for groups with multiple couples, but my friends and I made do with the beds. We really appreciated the attentive host and daily fresh bread, highly recommend staying here if it works for your budget and group."
Francesca L.
The price is AED 513
AED 901 total
includes taxes & fees
3 Nov - 4 Nov
20. Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of ParkingAlbany
8.0 out of 10, Very good, (1 review)
"Overall nice stay "
Anonymous traveler
The price is AED 878
AED 1,238 total
includes taxes & fees
22 Nov - 23 Nov
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.
Find vacation rentals that suit your style
Apartments
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Old Chatham Hotel Reviews
Berkshires Untold
10/10 Excellent
