Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence
Better together
Save up to NZ$616 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 Golf The Berkshires Hotels

Jiminy Peak Mountain Resort

37 Corey Rd Hancock MA

4 min walk from Jiminy Peak Mountain Resort

Stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular attractions ...

8.2/10 Very Good! (988 reviews)

This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ...

Reviewed on 5 Oct 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington MA

57 min drive from Jiminy Peak Mountain Resort

Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean ...

8.8/10 Excellent! (716 reviews)

Nice warm pool and hot tub. Good little fitness center.

Reviewed on 2 Jan 2026

The Orchards Hotel

222 Adams Rd Williamstown MA

25 min drive from Jiminy Peak Mountain Resort

Stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Colonial Plaza and Linear Park are ...

A little dated. Restaurant shut down for renovations, disappointing

Reviewed on 9 Mar 2020

See all 1,073 properties in The Berkshires

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.