Title: Windsor Vacation Packages 2026 from $536 | 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 $536 ## 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. ![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 $536 per person Jun 5 - Jun 7 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Cleveland (CLE) 7.6/10 Good! (1,008 reviews) The staff here is noting but fantastic. Weve stayed hwre twice in the past 3 months. Both times were great. We come up from wayne county ohio to watch cleveland sports. This location is nice as its walking discrance from rocket arena and progressive field. 4th street isnt too far of a walk either. We had a small issue with our room on our 2nd stay. We talked to the front desk and they immediately took care of it. 10 out of 10 very happy. Reviewed on Mar 31, 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 Save 100% on your flight $657 per person May 19 - May 22 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.8/10 Excellent! (1,026 reviews) Very nice hotel, staff were pleasant, and valet were quick Reviewed on Mar 29, 2026 ![Anchor Bay Inn and Suites](https://images.trvl-media.com/lodging/85000000/84090000/84083600/84083550/d23dc7eb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Anchor Bay Inn and Suites $658 per person May 15 - May 22 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Cleveland (CLE) 8.8/10 Excellent! (160 reviews) Room was very clean but the heat/ Reviewed on Oct 29, 2025 ![InterContinental Cleveland by IHG](https://images.trvl-media.com/lodging/1000000/920000/916400/916333/6d6c9251_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InterContinental Cleveland by IHG Fairfax Save 100% on your flight $645 per person May 19 - May 22 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 9/10 Wonderful! (872 reviews) All good except the mold/mildew in the shower Reviewed on Mar 2, 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 $671 per person May 19 - May 22 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.6/10 Excellent! (2,084 reviews) My room could’ve been much more cleaner. There was a lot of dust everywhere and also they did not change out the lotion in the bathroom, which is pretty unsanitary. And this day and age is not OK to be reusing the same opened lotion bottles. Staff was very kind and very attentive. The only issue I had was trying to call the front desk. It took several times for me to do so. Breakfast was very mid not anything to brag about and honestly it cost too much four dollars for a cup of orange juice is ridiculous. I didn’t have issues with Parking as I used public transportation i.e. Lyft to get me to the hotel. Reviewed on Mar 29, 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/2026-05-01/2026-05-08/?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 5 - Apr 6 Total with taxes and fees 7.4/10 Good! (1,000 reviews) The room wasn't as clean as previous stays here. The staff is always friendly. It is nice to be able to park right next to our room. Reviewed on Mar 31, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%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 $151 nightly $171 total Apr 9 - Apr 10 Total with taxes and fees 9.2/10 Wonderful! (841 reviews) Beautiful, lodge was very clean and staff was very friendly. Definitely will go back Reviewed on Mar 31, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&selected=1372060&PinnedHotelID=1372060&HadPinnedHotel=true®ionId=6180248) [See all 574 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F2%2F2026&endDate=4%2F3%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