Windsor Vacation Packages
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Your Windsor Vacation
Enjoy amazing adventures when you reserve a Windsor vacation package. Whether you're a history buff, foodie or just a traveler 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, organizing a tailored Windsor vacation is a walk in the park with Expedia.
Windsor Hotel Deals
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is CA $194 per night from May 3 to May 4
CA $194
CA $216 total
May 3 - May 4
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
We were happy with the room. Very spacious. The only downside was that the restaurant was closed to regular visitors.
Reviewed on Apr 27, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 3 to May 4
CA $118
CA $147 total
May 3 - May 4
includes taxes & fees
8.8/10 Excellent! (2,342 reviews)
Clean room staff it's respectful and easy going
Reviewed on Apr 28, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from May 21 to May 22
CA $123
CA $138 total
May 21 - May 22
includes taxes & fees
9/10 Wonderful! (921 reviews)
All was good. Wished there was coffee in the room and the heating / cooling system had an off switch. For one night and the price, it was fine. Cool bar & outside area.
Reviewed on Apr 30, 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.
