Windsor Vacations from $306
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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.
Embassy Suites by Hilton Cleveland Rockside
Price was $492, price is now $306 per person
$306
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Cleveland (CLE)
7.4/10 Good! (1,002 reviews)
Everything was great but the view from the bedroom. I would definitely stay again.
Reviewed on Nov 23, 2025
Fidelity Hotel
Downtown Cleveland
Price was $668, price is now $370 per person
$370
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Cleveland (CLE)
9.6/10 Exceptional! (471 reviews)
Exceptional hotel! The boutique style and decor are a perfect fit for the historic building. Loved all the thoughtful design features. I ended up getting upgraded to a King Room so that was a pleasant surprise. Beds were incredibly comfy and the bathroom was stunning with the mosaic tiles. I asked for extra pillows prior to my stay and boy, did they deliver!! The service was prompt and extremely friendly. Club Room was a wonderful restaurant and the food absolutely delicious. Valet is pricy, but incredibly convenient being open 24 hrs and also quick, so worth the daily rate to avoid parking fees in a garage. The hotel is in perfect walking distance to Rocket Arena. I would stay here again in a heartbeat.
Reviewed on Nov 30, 2025
The Westin Cleveland Downtown
Downtown Cleveland
Price was $548, price is now $310 per person
$310
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Cleveland (CLE)
8.6/10 Excellent! (1,771 reviews)
The room was spotless and the staff was EXTREMELY courteous. I would definitely recommend this hotel.
Reviewed on Nov 28, 2025
Kimpton Schofield Hotel by IHG
Downtown Cleveland
Save 100% on your flight
Price was $831, price is now $488 per person
$488
per person
Feb 10 - Feb 16
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Cleveland (CLE)
8.6/10 Excellent! (1,006 reviews)
Awesome place to stay in downtown Cleveland! Room was great, location was awesome. Would stay again
Reviewed on Nov 28, 2025
Residence Inn By Marriott Cleveland Downtown
Downtown Cleveland
Price was $522, price is now $308 per person
$308
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Cleveland (CLE)
8.2/10 Very Good! (1,000 reviews)
Great location in downtown area, with short walk to restaurants and Rocket Arena. Hotel and room were clean, personnel were pleasant and bed was comfortable. The breakfast was included and it was nice quality. Overall, very happy with our stay and will be back!
Reviewed on Nov 26, 2025
Discover the most popular places to visit in Windsor
Windsor Mills Covered Bridge
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
$61 nightly
The price is $70 total per night from Dec 4 to Dec 5
$70 total
Dec 4 - Dec 5
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
I had two dogs with me, so being able to step right outside with them when they needed to potty was super convenient.
Reviewed on Nov 11, 2025
Red Roof Inn Ashtabula - Austinburg
1860 Austinburg-Ashtabula Rd Austinburg OH
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $72 total per night from Dec 3 to Dec 4
$72 total
Dec 3 - Dec 4
Total with taxes and fees
6.8/10 (888 reviews)
Clean rooms. Great staff. Very polite staff at the front desk. Awesome stay!
Reviewed on Nov 24, 2025
Comfort Inn
7581 Auburn Rd Painesville OH
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Dec 28 to Dec 29
$116 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
Clean room ..staff very helpful and friendly .. overall very nice experience . But would recommended more handicap parking spots closer to main entrance
Reviewed on Nov 29, 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 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Riverdale Road Covered Bridge and Windsor Mills Covered Bridge |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
