Berkshire County Holiday Packages

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A town hall with a central dome and columns, surrounded by trees and people.
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Lenox

Lenox
The Purple Pub with outdoor seating and autumn foliage.
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Williamstown

Williamstown
A row of parked cars along a street lined with brick buildings, including a sign for 'Vault Studio' and 'Hotpoint'.
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Great Barrington

Great Barrington

Top Berkshire County hotels

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$297 per night from 14 Sept to 15 Sept
NZ$297
14 Sept - 15 Sept
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
"Free Breakfasts were excellent, but the room was tired, bathroom and shower very small"

Reviewed on 20 Aug 2026

Opens in a new windowThe Yankee Inn
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 NZ$216 per night from 31 Aug to 1 Sept
NZ$216
31 Aug - 1 Sept
includes taxes & fees
Stay at this golf aparthotel in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in ...
"Pleasant place to stay. About 10 minutes from Tanglewood. Alpha centrally located to many things to do in the Berkshire area."

Reviewed on 20 Aug 2026

Opens in a new windowBerkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 31 Aug to 1 Sept
NZ$182
31 Aug - 1 Sept
includes taxes & fees
Stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in ...
"We come up to the Berkshires every year for Tanglewood and always stay here. The rooms are always clean and the staff friendly and helpful. The rooms have either a full kitchen or kitchenette so at the very least you can have coffee when you wake-up. The fact that Vacation Village is on Brodie Mountain ..."

Reviewed on 20 Aug 2026

Opens in a new windowVacation Village in the Berkshires
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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.