Windsor Holidays
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Your Windsor Holiday
Enjoy amazing adventures when you reserve a Windsor holiday package. Whether you're a history buff, foodie or just a traveller who loves discovering new places, there's something for everyone in this awesome city. If seeing the sights is a priority during your trip to Windsor, make sure you swing by popular attractions like Wahconah Falls State Park and Bas Ridge Golf Course. No matter your travel plans or the size of your budget, organising a tailored Windsor holiday is a walk in the park with Expedia.
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 890 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Barrington Stage Company, Colonial Theatre and Berkshire Museum |
Top hotels in Windsor
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is £88 per night from 27 May to 28 May
£88
27 May - 28 May
includes taxes & fees
9/10 Wonderful! (931 reviews)
These are all 1 bedroom suites. There was plenty of room in kitchen cupboards for our groceries. The kitchen was well supplied with cooking utensils, dishes and glassware. The location is excellent with several grocery stores and restaurants close by. Everything was perfect except for the height ...
Reviewed on 11 May 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
The price is £94 per night from 17 May to 18 May
£94
17 May - 18 May
includes taxes & fees
9/10 Wonderful! (941 reviews)
Great experience
Reviewed on 13 May 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is £79 per night from 17 May to 18 May
£79
17 May - 18 May
includes taxes & fees
8.8/10 Excellent! (2,355 reviews)
Everything was great!
Reviewed on 10 May 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. Flight-inclusive packages are ATOL protected.
