Title: Windsor Vacation Packages 2026 from $344 | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx6180248)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d6180248.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d6180248.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d6180248.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d6180248.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6046880/887631b2-e098-411d-ad6d-5a87b7d10913.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor Vacations from $344 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Windsor-Mills-Covered-Bridge-Windsor.d6180252.Vacation-Attraction). 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. ![The Tudor Arms Hotel Cleveland - a DoubleTree by Hilton](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287341/52897d1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Tudor Arms Hotel Cleveland - a DoubleTree by Hilton University Circle Save 100% on your flight $344 per person May 8 - May 11 found 1 day ago Roundtrip flight included New York (NYC) to Cleveland (CLE) 8.2/10 Very Good! (1,138 reviews) The hotel has a free shuttle that took us to Cleveland clinic and hotel allowed us to leave our vehicle in their parking lot. They came back and got us after our appt. It was wonderful. We were not familiar with the clinic campuses so it helped immensely. Reviewed on Mar 19, 2026 ![The Washington Boutique Hotel](https://images.trvl-media.com/lodging/100000000/99990000/99982700/99982661/391bcf5c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Washington Boutique Hotel Save 100% on your flight $814 per person Jun 21 - Jun 24 found 22 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Cleveland (CLE) 9/10 Wonderful! (85 reviews) Room was clean and cute decor, there is no staff, more like an air bnb….and there is no parking. There a small parking lot on the s Reviewed on Mar 11, 2026 ![Kimpton Schofield Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13190000/13181300/13181279/ba15d366_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Schofield Hotel by IHG Downtown Cleveland $584 per person Jun 5 - Jun 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Cleveland (CLE) 8.8/10 Excellent! (1,026 reviews) Our room had a walk-in shower, which was outstanding. Room had two sinks on either side of the shower that was an added nicety for two people. Bed was comfortable and there was access to many outlets for charging your phone/tablet/etc. Staff was wonderful and the onsite Betts restaurant was superb. Loved the sit down area in the lobby with a fireplace and access to coffee, etc. Reviewed on Mar 24, 2026 ![The Westin Cleveland Downtown](https://images.trvl-media.com/lodging/1000000/10000/3400/3332/a3be6d16_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Cleveland Downtown Downtown Cleveland Save 100% on your flight $981 per person Jun 5 - Jun 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Cleveland (CLE) 8.6/10 Excellent! (2,084 reviews) Great experience will definately book again Reviewed on Mar 16, 2026 ![Hilton Garden Inn Cleveland Downtown](https://images.trvl-media.com/lodging/1000000/870000/866100/866043/2d490d61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Cleveland Downtown Downtown Cleveland Save 100% on your flight $535 per person May 8 - May 11 found 1 day ago Roundtrip flight included New York (NYC) to Cleveland (CLE) 7.6/10 Good! (1,008 reviews) As expected. Very nice Reviewed on Mar 23, 2026 Don't see what you're looking for? See all available trips from Columbus to Windsor [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-26/2026-05-03/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CGF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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. [](https://expedia.com/Windsor-Mills-Covered-Bridge-Windsor.d6180252.Vacation-Attraction) ## Windsor Hotel Deals ![Red Roof Inn Cleveland - Mentor/ Willoughby](https://images.trvl-media.com/lodging/1000000/20000/13800/13716/7c09b76c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Red Roof Inn Cleveland - Mentor/ Willoughby 4166 State Route 306 Willoughby OH Fully refundableReserve now, pay when you stay $61 nightly $70 total Apr 1 - Apr 2 Total with taxes and fees 7.4/10 Good! (1,000 reviews) Can't expect much from a cheap motel like this. Bed was comfortable. But 2nd floor with no elevator access makes it hard when you are partially handicapped. Parking plentiful but was concerned about car safety, so I had to bring everything from the car into my room which was very small. Not business ... Reviewed on Mar 10, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=13716&PinnedHotelID=13716&HadPinnedHotel=true®ionId=6180248) ![Best Western Plus Mentor-Cleveland Northeast](https://images.trvl-media.com/lodging/1000000/660000/660000/659951/6708ea96_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Mentor-Cleveland Northeast 8434 Mentor Avenue Mentor OH Fully refundableReserve now, pay when you stay $101 nightly $117 total Apr 8 - Apr 9 Total with taxes and fees 9.2/10 Wonderful! (1,000 reviews) Very clean. Nice staff. Good breakfast. Decor was dated but well maintained. Only drawback is hearing the street noises as sirens/emergency was close by. Would recommend staying here. Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F8%2F2026&endDate=4%2F9%2F2026&selected=659951&PinnedHotelID=659951&HadPinnedHotel=true®ionId=6180248) ![The Lodge at Geneva](https://images.trvl-media.com/lodging/2000000/1380000/1372100/1372060/16d56c9d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Lodge at Geneva 4888 N. Broadway Geneva OH Fully refundableReserve now, pay when you stay $130 nightly $147 total Mar 29 - Mar 30 Total with taxes and fees 9.2/10 Wonderful! (837 reviews) The staff was great. Very clean and quiet. The pool and hot tub was amazing. We will return. Reviewed on Mar 15, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=1372060&PinnedHotelID=1372060&HadPinnedHotel=true®ionId=6180248) [See all 564 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F27%2F2026&endDate=3%2F28%2F2026®ionId=6180248) 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](https://www.expedia.com/Riverdale-Road-Covered-Bridge-Rock-Creek.d6180212.Vacation-Attraction) and [Windsor Mills Covered Bridge](https://www.expedia.com/Windsor-Mills-Covered-Bridge-Windsor.d6180252.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations 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Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app