Windsor Vacations from $666
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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.
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
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
$125 nightly
The price is $139 total per night from Jun 29 to Jun 30
$139 total
Jun 29 - Jun 30
Total includes taxes and fees
8.6/10 Excellent! (1,835 reviews)
"We always stay here because it’s the best value and so beautiful."
Reviewed on Jun 23, 2025
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd, South Deerfield, MA
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $89 total per night from Jul 6 to Jul 7
$89 total
Jul 6 - Jul 7
Total includes taxes and fees
7/10 Good! (1,004 reviews)
"Good Location"
Reviewed on Jun 16, 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $179 total per night from Jun 30 to Jul 1
$179 total
Jun 30 - Jul 1
Total includes taxes and fees
9/10 Wonderful! (660 reviews)
Good for a girls trip!
"We loved the comfortable beds and ensuite bathrooms. The kitchen was well-equipped and common room was comfortable too. We didn't use any of the other amenities, but there were quite a few options that looked appealing. Convenient to Lenox which was our primary destination for dining and ..."
Reviewed on Jun 21, 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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