Hillsdale Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$233 per night from 7 July to 8 July
AU$233
7 July - 8 July
includes taxes & fees
9/10 Wonderful! (968 reviews)
"Very spacious and a good spot if you like to cook for yourself. Decor is dated but it's clean and good value."
Reviewed on 7 June 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is AU$176 per night from 22 June to 23 June
AU$176
22 June - 23 June
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub ..."
Reviewed on 8 June 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 11 June to 12 June
AU$198
11 June - 12 June
includes taxes & fees
9/10 Wonderful! (977 reviews)
"The room was very nice, but a little small. The biggest issue we had is the room was VERY dark. One desk lamp had 2 lights, that one was fine. On the table between the beds there was a tiny lamp with a sort of orange colored very dim bulb. Quite useless. There was a floor lamp in the corner that ..."
Reviewed on 7 June 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
