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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.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Windsor Hotel Deals
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Oct. 1 to Oct. 2
CA $193
CA $216 total
includes taxes & fees
Oct 1 - Oct 2
9/10 Wonderful! (398 reviews)
Ny new favorite hotel in the Berkshires !
"Woa, this place is nice ! It used to be a motel, but do NOT deter you. Everything was impeccable and gorgeous. I ate breakfast and dinner at the restaurant and sat on the patio for a couple hours reading. Everything was just lovely ! Beautiful garden style patio with comfortable furniture. Elegant ..."
Reviewed on Sep. 25, 2024
The Red Lion Inn
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $308 per night from Oct. 2 to Oct. 3
CA $308
CA $405 total
includes taxes & fees
Oct 2 - Oct 3
8.8/10 Excellent! (991 reviews)
"Lovely old hotel with excellent bar and restaurant. Central to all Berkshire sights. Room clean and well-appointed; wonderful shower; lobby and many nooks in which to curl up with drink and a good book… Ambassador felines Jane and Jack make Red Lion Inn feel like home."
Reviewed on Sep. 18, 2024
Hotel Downstreet
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Sep. 29 to Sep. 30
CA $151
CA $169 total
includes taxes & fees
Sep 29 - Sep 30
8.6/10 Excellent! (1,003 reviews)
"The hotel has a very cool vibe. The staff was very helpful and welcoming. Their restaurant recommendations were very good."
Reviewed on Sep. 25, 2024
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.