
Hillsdale Holidays
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Your Hillsdale Holiday
The rich history and welcoming locals are just the beginning of the things Hillsdale has on offer. Enjoy the sights and sounds of this lively city your way with a customised Hillsdale holiday package. There's plenty to include on your must-do list during a trip to Hillsdale, beginning with popular sights such as Taconic State Park and Catamount Aerial Adventure Park. A few clicks is all it takes to put together a tailor-made Hillsdale holiday on Expedia.
Hillsdale Holiday
Hillsdale Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Lake Taghkanic State Park, Hudson Chatham Winery and Catamount Aerial Adventure Park |
Our pick of the best Hillsdale Hotel Deals

The Brooks Motel
2871 New York 23, Hillsdale, NY
Fully refundableReserve now, pay when you stay
7.4/10 Good! (109 reviews)
"The room was very comfortable & clean. It had a really nice shower, which is very important for us when travelling. Thank you! See you again some time."
Reviewed on 4 Oct 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$194 per night from 5 Nov to 6 Nov
AU$194
5 Nov - 6 Nov
includes taxes & fees
8.8/10 Excellent! (698 reviews)
"Clean spacious."
Reviewed on 13 Oct 2025

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 2 Nov to 3 Nov
AU$150
2 Nov - 3 Nov
includes taxes & fees
9/10 Wonderful! (756 reviews)
"We had a nice room and the food was delicious. Great place to stay."
Reviewed on 13 Oct 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.