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
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 2 Nov to 3 Nov
AU$174
2 Nov - 3 Nov
includes taxes & fees
8.6/10 Excellent! (2,097 reviews)
Check in was easy. Room was clean and well-stocked. Lay out for the double room was great. Pool was well-maintained. Game room was added benefit. Very nice stay.
Reviewed on 24 Oct 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 2 Nov to 3 Nov
AU$166
2 Nov - 3 Nov
includes taxes & fees
9/10 Wonderful! (726 reviews)
Clean room
Reviewed on 23 Oct 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundable
The price is AU$177 per night from 2 Nov to 3 Nov
AU$177
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (917 reviews)
All was very good at this hotel, our room was modernized and updated. The people at the front desk as well as all the employees were all well trained and pleasant . Pittsfield is in the middle of The Berkshires and so it was a great location to see what we wanted to see.
Reviewed on 22 Oct 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.
