Hillsdale Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿4,531 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
Top hotels in Hillsdale
The Brooks Motel
2871 New York 23 Hillsdale NY
Fully refundableReserve now, pay when you stay
7.4/10 Good! (123 reviews)
So peaceful and beautiful. Very clean !
Reviewed on 29 Dec 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ฿3,188 per night from 11 Jan to 12 Jan
฿3,188
฿3,561 total
11 Jan - 12 Jan
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
The room was clean, comfortable and spacious. The bathroom had enough space and was clean and well appointed.
Reviewed on 30 Dec 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is ฿2,922 per night from 4 Jan to 5 Jan
฿2,922
฿3,264 total
4 Jan - 5 Jan
includes taxes & fees
8/10 Very Good! (998 reviews)
While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance
Reviewed on 22 Dec 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.
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.
