Windsor Holidays

Name: Vacation Village in the Berkshires
Price range: AU$149
Rating: 8.8

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Your Windsor Holiday

Our holiday packages to Windsor let you customise your own adventure. Tailor your journey to your interests and style and make the most of your time in this interesting city. Want some sightseeing tips for your trip to Windsor? Wahconah Falls State Park and Bas Ridge Golf Course are two of the main attractions here. Whatever your travel plans or the size of your budget, organising a tailored Windsor holiday is a walk in the park with Expedia.

Windsor Holiday

Windsor Essential Information

Language	English
Currency	U.S dollars
Population	890
Max Temp Winter	-1.11ºC
Max Temp Summer	24ºC
Top Sights	Berkshire Museum, Colonial Theatre and Barrington Stage Company

Our pick of the best Windsor Hotel Deals

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

AU$166

24 May - 25 May

includes taxes & fees

9/10 Wonderful! (925 reviews)

Room very spacious and clean. Full kitchen is a great bonus.

Reviewed on 4 May 2026

Berkshires Untold

194 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

AU$151

12 May - 13 May

includes taxes & fees

9/10 Wonderful! (932 reviews)

Easy, comfortable and convenient; rooms and public spaces are nice, modern and stylish updates of modest 60s/70s original motel facilities.

Reviewed on 6 May 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

AU$149

11 May - 12 May

includes taxes & fees

8.8/10 Excellent! (2,351 reviews)

I loved my stay at the resort! The view was beautiful, my room was clean, and the staff were nice. I had trouble with my door, and they sent someone quickly to fix it.

Reviewed on 8 May 2026

See all 1,000 properties in Windsor

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.