Hillsdale Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Hillsdale

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is €103 per night from 24 May to 25 May
€103
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (933 reviews)
Clean and great job staffing

Reviewed on 15 May 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is €120 per night from 19 May to 20 May
€120
19 May - 20 May
includes taxes & fees
9/10 Wonderful! (945 reviews)
Very nice as long as you know 1) it’s a roadside 2-story motel (the kind you drive your car in front of your door) facing a very busy 4-lanes of traffic road so lots of traffic noise and 2) getting onto property is a left or right turn from the above mentioned busy road with no turn lane. It’s a ...

Reviewed on 15 May 2026

Berkshires Untold
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
The price is €184 per night from 20 May to 21 May
€184
20 May - 21 May
includes taxes & fees
9.6/10 Exceptional! (224 reviews)
It was exactly what we wanted.

Reviewed on 15 May 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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.