Hillsdale Holidays
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Top hotels in Hillsdale
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is S$234 per night from 21 Jun to 22 Jun
S$234
21 Jun - 22 Jun
includes taxes & fees
9/10 Wonderful! (984 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
The price is S$159 per night from 22 Jun to 23 Jun
S$159
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
The price is S$142 per night from 18 Jun to 19 Jun
S$142
18 Jun - 19 Jun
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Employees were very helpful."
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
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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. 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.
