Massachusetts Ski Holidays
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Price found within the past 48 hours. Click for updated prices.
Doubletree by Hilton Hotel Leominster
per person
9 Aug - 15 Aug
found 11 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (1,002 reviews)
The easy chair in the room was dirty and the stuffing was coming out of the seat. Otherwise, it was a good room.
There were no water bottles in the room upon arrival.
Reviewed on 8 Jul 2025
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Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,856 reviews)
"This is more like renting a small condo, though I booked it as a "hotel room". Lots of families, plenty for them to do on premises, barbeque pits, activities, multiple pools and water features for the kids. It is a massive development at the foot of a ski resort in rural Western Massachusetts. The ..."
Reviewed on 6 Jul 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
The price is €153 per night from 21 Jul to 22 Jul
€153
21 Jul - 22 Jul
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,006 reviews)
"It only gets better every year"
Reviewed on 7 Jul 2025
Jiminy Peak Mountain Resort
37 Corey Rd, Hancock, MA
The price is €153 per night from 22 Jul to 23 Jul
€153
22 Jul - 23 Jul
includes taxes & fees
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 bars/lounges. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (947 reviews)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
Reviewed on 7 Jul 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.