Windsor Vacations from $441
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Your Windsor Vacation
When you book a Windsor vacation package, you can relax and enjoy your adventure to the fullest. Uncover the highlights of this fascinating city knowing that all your travel needs have been taken care of before you go. During your trip to Windsor, carve some time in your schedule for sightseeing. A popular place to start exploring is Windsor Mills Covered Bridge. Don't put off your visit to this destination any longer. The perfect Windsor vacation is a couple of clicks away with Expedia.
The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Cleveland Downtown
Downtown Cleveland
Save 100% on your flight
Price was $696, price is now $441 per person
$441
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.6/10 Good! (1,022 reviews)
Close to Guardians stadium made it very nice. Close to downtown. Nice to be able to park there and walk to the game.
Reviewed on Jun 1, 2026
The Tudor Arms Hotel Cleveland - a DoubleTree by Hilton
University Circle
Save 100% on your flight
Price was $878, price is now $610 per person
$610
per person
Aug 22 - Aug 29
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.2/10 Very Good! (1,138 reviews)
Every time I’ve visited my daughter and family, I’ve stayed at Tudor Arms. My only issue was the roadwork at front of hotel but was not the hotel’s fault. Our stay was great!
Reviewed on May 31, 2026
ROOST Cleveland
Downtown Cleveland
Save 100% on your flight
Price was $864, price is now $629 per person
$629
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (732 reviews)
Roost is a great value very large apartment style living in downtown. Couple small downsides, the bed is very low to the floor (but comfortable), HVAC is loud could be a problem for a light sleeper but I like background noise. Also because it is not a traditional hotel there is no restaurant or freshly made coffee in the morning so prepare for that accordingly.
Reviewed on Jun 1, 2026
Discover the most popular places to visit in Windsor
Windsor Mills Covered Bridge
5/5(3 reviews)
Learn about the local history of Windsor when you take a trip to Windsor Mills Covered Bridge. Experience the area's festivals and entertainment venues.
Windsor Hotel Deals
Red Roof Inn Cleveland - Mentor/ Willoughby
4166 State Route 306 Willoughby OH
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $72 total per night from Jun 14 to Jun 15
$72 total
Jun 14 - Jun 15
Total with taxes and fees
7.4/10 Good! (1,006 reviews)
"This visit was a little disappointing. There was no soap in the room and the bathtub appeared that it hadn't been cleaned. I was told to park in front of the of the assigned room, but when I arrived there at 7 o'clock there was no space there."
Reviewed on May 31, 2026
The Lodge at Geneva
4888 N. Broadway Geneva OH
$220 nightly
The price is $250 total per night from Jun 14 to Jun 15
$250 total
Jun 14 - Jun 15
Total with taxes and fees
9.2/10 Wonderful! (865 reviews)
"The property was immaculate. The staff was all friendly and helpful. The restaurant attached to it was amazing for all types of food! Very accommodating! We can’t wait to return"
Reviewed on May 31, 2026
Wingate by Wyndham Geneva at SPIRE Academy
1715 S Broadway Geneva OH
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $111 total per night from Jun 14 to Jun 15
$111 total
Jun 14 - Jun 15
Total with taxes and fees
9.2/10 Wonderful! (79 reviews)
"Fantastic hotel!"
Reviewed on May 31, 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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Riverdale Road Covered Bridge and Windsor Mills Covered Bridge |
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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.
