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
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is £117 per night from 22 Apr to 23 Apr
£117
22 Apr - 23 Apr
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The ...
Reviewed on 22 Mar 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is £90 per night from 28 Apr to 29 Apr
£90
28 Apr - 29 Apr
includes taxes & fees
9/10 Wonderful! (888 reviews)
very clean and friendly staff
Reviewed on 24 Mar 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is £59 per night from 31 Mar to 1 Apr
£59
31 Mar - 1 Apr
includes taxes & fees
9/10 Wonderful! (882 reviews)
I spent 2 lovely nights here on my way through the Berkshires. Everyone was so kind, helpful and professional. Flatbread was delicious and a cup of tea in the cozy fire nook was perfect.
Reviewed on 28 Mar 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.