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Windsor Holidays
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Our pick of the best Windsor Hotel Deals
![Life House Berkshires](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 24 Jun to 25 Jun
NZ$217
per night
24 Jun - 25 Jun
9/10 Wonderful! (268 reviews)
One night away with kids
"Wonderful little get away with the family - the hotel was lovely, we had a great breakfast and a hike across the street at Kennedy Park."
Reviewed on 20 Jun. 2024
![Hotel Downstreet](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/644e76fa_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hotel Downstreet
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is NZ$272 per night from 23 Jun to 24 Jun
NZ$272
per night
23 Jun - 24 Jun
8.4/10 Very Good! (930 reviews)
Nifty hotel in a great little town
"The room was clean and distinctive. Everything worked properly. The hotel is perfectly located for accessing anything in town by foot, including MassMOCA and various eateries."
Reviewed on 16 Jun. 2024
![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/96ff6d07_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$228 per night from 26 Jun to 27 Jun
NZ$228
per night
26 Jun - 27 Jun
9/10 Wonderful! (1,001 reviews)
Pleasantly surprised
"We had a good experience here! The staff was AWESOME! They were very helpful in checking in and gave us good info. They have a bar but it was not open during the times we were in and out. The breakfast was good and we enjoyed the omelet. Its only on the weekend--wish it was every day! The pool was ..."
Reviewed on 15 Jun. 2024
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.