
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.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.




Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Save 100% on your flight
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Albany (ALB)
9/10 Wonderful! (667 reviews)
Wonderful SPACIOUS spotless unit with full kitchen, table and chair set, lovely forest view deck, two bathrooms, separate bedrooms and a comfortable sleep sofa!! Only problem was that there was no elevator to take our pieces of luggage to the third level. And we are Senior citizens! Otherwise, a great facility!
Reviewed on Jul. 14, 2025
Windsor Hotel Deals

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 Jul 17 to Jul 18
CA $118
CA $147 total
Jul 17 - Jul 18
includes taxes & fees
8.6/10 Excellent! (1,873 reviews)
"I loved the pool for the kids, it a quiet place"
Reviewed on Jul. 13, 2025

Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd, South Deerfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jul 31 to Aug 1
CA $159
CA $178 total
Jul 31 - Aug 1
includes taxes & fees
7/10 Good! (1,006 reviews)
"It was clean and served our purpose just fine"
Reviewed on Jul. 14, 2025

The Williams Inn
101 Spring Street, Williamstown, MA
The price is CA $325 per night from Aug 11 to Aug 12
CA $325
CA $364 total
Aug 11 - Aug 12
includes taxes & fees
9.6/10 Exceptional! (467 reviews)
"Hrwat"
Reviewed on Jul. 11, 2025
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.