Windsor Vacations from $774
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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.
The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
The Equinox Golf Resort & Spa
Save 100% on your flight
per person
Aug 8 - Aug 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
7.4/10 Good! (483 reviews)
I had a wonderful time and did Rhumba for the first time in the pool!
Lovely walk to the pond also!
Reviewed on Jun 23, 2025
DoubleTree by Hilton Schenectady Downtown
Seward Place
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
8.4/10 Very Good! (662 reviews)
Overall nice clean hotel . Need to update tvs so you can use streaming services. Need to update website about complimentary breakfast and late check out .
Reviewed on Jun 1, 2025
Windsor Hotel Deals
Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Jul 13 to Jul 14
$170 total
Jul 13 - Jul 14
Total includes taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Very cute hotel. The room was huge and the staff were friendly."
Reviewed on Jun 29, 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
8.6/10 Excellent! (1,836 reviews)
"The property was perfect for a getaway. 1 bedroom suite or more with balconies. Non heating Fireplace for aesthetics. The suite was a jack and Jill! Shower, but also a jet tub separate from shower. All dishes and cooking utensils that you needed. You can grill onsite or cook in your suite as take ..."
Reviewed on Jun 24, 2025
The Williams Inn
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $263 total per night from Jul 10 to Jul 11
$263 total
Jul 10 - Jul 11
Total includes taxes and fees
9.6/10 Exceptional! (458 reviews)
"Wonderful stay. Helpful, professional staff."
Reviewed on Jun 27, 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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 890 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Colonial Theater, Barrington Stage Company and Berkshire Museum |
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- Wahconah Falls State Park
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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.