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Our top choices for Hillsdale holiday homes
1. Fantastic 2-bedroom house with AC in quaint Hillsdale.
Fantastic 2-bedroom house with AC in quaint Hillsdale.Hillsdale
The price is AU$913
includes taxes & fees
21 Nov - 22 Nov
2. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
Janet G.
The price is AU$459
includes taxes & fees
9 Nov - 10 Nov
3. All the comforts of home
All the comforts of homeHudson
9.2 out of 10, Wonderful, (38 reviews)
"Great location and super welcoming "
Julie B.
The price is AU$193
includes taxes & fees
8 Nov - 9 Nov
4. 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 AU$420
includes taxes & fees
8 Nov - 9 Nov
5. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 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."
Kelly B.
The price is AU$427
includes taxes & fees
8 Nov - 9 Nov
6. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is AU$582
includes taxes & fees
19 Nov - 20 Nov
7. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
10.0 out of 10, Exceptional, (10 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
Roberta
The price is AU$1,756
includes taxes & fees
8 Nov - 9 Nov
8. Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
Mary R.
The price is AU$946
includes taxes & fees
16 Nov - 17 Nov
9. 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 AU$284
includes taxes & fees
8 Nov - 9 Nov
10. 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, (17 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 AU$465
includes taxes & fees
8 Nov - 9 Nov
11. 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 AU$310
includes taxes & fees
8 Nov - 9 Nov
12. 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 AU$894
includes taxes & fees
9 Nov - 10 Nov
13. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to WarrenHudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
Brittaney O.
The price is AU$614
includes taxes & fees
8 Nov - 9 Nov
14. Modern cabin retreat
Modern cabin retreatCatskill
The price is AU$353
includes taxes & fees
3 Dec - 4 Dec
15. Cabin Oasis near Town
Cabin Oasis near TownCatskill
The price is AU$386
includes taxes & fees
16 Nov - 17 Nov
16. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is AU$1,820
includes taxes & fees
16 Nov - 17 Nov
17. Cozy Catskill Escape
Cozy Catskill EscapeCatskill
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating host. Great with last minute visits."
Kevin P.
The price is AU$369
includes taxes & fees
30 Nov - 1 Dec
18. 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 AU$975
includes taxes & fees
9 Nov - 10 Nov
19. 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 AU$839
includes taxes & fees
16 Nov - 17 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.
Learn more about Hillsdale
Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.
