Windsor Holidays
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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
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is AU$193 per night from 4 Jan to 5 Jan
AU$193
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (2,170 reviews)
Awesome for ski
Reviewed on 14 Dec 2025
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is AU$314 per night from 23 Dec to 24 Dec
AU$314
23 Dec - 24 Dec
includes taxes & fees
9.6/10 Exceptional! (549 reviews)
Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick.
Reviewed on 7 Dec 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 20 Dec to 21 Dec
AU$149
20 Dec - 21 Dec
includes taxes & fees
8/10 Very Good! (988 reviews)
Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful .
Reviewed on 15 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.
