Title: Windsor Vacation Packages 2026 from $353 | 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 $353 ## Book a Hotel + Flight or Car together to unlock savings ## 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 $353 per person May 3 - May 6 found 12 hours ago Roundtrip flight included New York (JFK) 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 ![The Inn at Fulton](https://images.trvl-media.com/lodging/103000000/102660000/102658400/102658389/2099735d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Fulton Save 100% on your flight $677 per person Jun 26 - Jun 28 found 10 hours ago Roundtrip non-stop flight included Boston (BOS) to Cleveland (CLE) 8.2/10 Very Good! (36 reviews) Looked just like the pictures. Very clean. Only thing i would say is it only had one bathroom and that bathroom is located inside the master room so the other guest had to come in that room to use the bathroom so just be prepared for that. Other than that loved the area and place. Reviewed on Dec 27, 2025 ![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 $828 per person Jun 26 - Jun 28 found 10 hours ago Roundtrip non-stop flight included Boston (BOS) to Cleveland (CLE) 9/10 Wonderful! (86 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 ![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 $523 per person May 21 - May 25 found 1 day ago Roundtrip flight included Atlanta (ATL) 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 ![Hampton Inn Cleveland-Westlake](https://images.trvl-media.com/lodging/1000000/10000/8800/8722/a2a41532_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn Cleveland-Westlake $493 per person May 21 - May 25 found 1 day ago Roundtrip flight included Atlanta (ATL) to Cleveland (CLE) 8.2/10 Very Good! (1,005 reviews) The staff at this hotel was excellent and very hospitable and was the highlight of my experience staying there. They offered complimentary water bottles at check in and had a message on the TV to welcome us when we got to our room. They were attentive and very nice throughout our stay. The room furniture was really nice looking. The desk proved to be the perfect table for my 2 year old to use her coloring books. The other little desk in the room was perfect height for a makeshift changing table. The bathroom unfortunately did not have a tub like was listed in the expedia listing, just a shower (only care because we have a young child). There was no fan in the bathroom. The room was mostly clean but we did find an empty condom wrapper behind the chair. I would say the 2 biggest pain points for me was the bed/pillows were very uncomfortable and made it hard to sleep. And the second being that I thought the breakfast was not as great as previous reviews had claimed- in particular a lot of the fruit that was out had gone bad, the yogurt left out was warm, and other food options did not taste very great. But I felt the waffle maker was my go to during my stay and did not disappoint. The eating area was abnormally dim. We noticed that the elevator was not heated and the other elevator has been broken for a long time. Overall the staff was the highlight of our experience and the stay itself was very average with some pain points, but we are grateful for the stay. Reviewed on Mar 30, 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/2026-05-03/2026-05-10/?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 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 7 - Apr 8 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%2F7%2F2026&endDate=4%2F8%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 $163 nightly $184 total Apr 14 - Apr 15 Total with taxes and fees 9.2/10 Wonderful! (842 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%2F14%2F2026&endDate=4%2F15%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%2F4%2F2026&endDate=4%2F5%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.