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
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is AU$249 per night from 30 June to 1 July
AU$249
30 June - 1 July
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"No real breakfast"
Reviewed on 21 June 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$232 per night from 7 July to 8 July
AU$232
7 July - 8 July
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."
Reviewed on 23 June 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 8 July to 9 July
AU$209
8 July - 9 July
includes taxes & fees
8.8/10 Excellent! (2,409 reviews)
"The room was great. Had everything I needed and was very comfortable."
Reviewed on 24 June 2026
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.
