Hillsdale Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is S$231 per night from 19 Jul to 20 Jul
S$231
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (987 reviews)
"The value for the price was outstanding! This place is really nice. \"
Reviewed on 17 Jun, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is S$182 per night from 22 Jun to 23 Jun
S$182
22 Jun - 23 Jun
includes taxes & fees
9.2/10 Wonderful! (1,016 reviews)
"My room was very clean and tidy. The mattress was a little old, but still comfortable enough to sleep on. The choice of an outdoor or indoor pool was much appreciated. Overall, this hotel was a good value."
Reviewed on 16 Jun, 2026
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
The price is S$149 per night from 21 Jun to 22 Jun
S$149
21 Jun - 22 Jun
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Great staff, clean, air conditioned room and breakfast included. Just what I needed!"
Reviewed on 17 Jun, 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.
Stay near popular Hillsdale attractions
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
