Middlefield Packages (Flight + Hotel)
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Top hotels in Middlefield
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is ฿3,277 per night from 5 Jan to 6 Jan
฿3,277
฿4,006 total
5 Jan - 6 Jan
includes taxes & fees
8.6/10 Excellent! (2,195 reviews)
No frills stay with a kitchen and dishwasher (make sure your room has one— some do not!!!). Location is across the street from Jiminy Peak, so skiing can be accomplished almost as easy as staying on their property. This is our fourth time staying and it always serves its purpose.
Reviewed on 30 Dec 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is ฿2,922 per night from 8 Jan to 9 Jan
฿2,922
฿3,264 total
8 Jan - 9 Jan
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Staff was very pleasant and friendly. From front desk to valet.
Reviewed on 1 Jan 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ฿3,188 per night from 11 Jan to 12 Jan
฿3,188
฿3,561 total
11 Jan - 12 Jan
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
The room was clean, comfortable and spacious. The bathroom had enough space and was clean and well appointed.
Reviewed on 30 Dec 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.
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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.
