Title: Windsor Vacation Packages 2026 from $152 | 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 $152 ## 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. ![Cedar Stables Inn and Suites](https://images.trvl-media.com/lodging/36000000/35900000/35895300/35895256/0630393b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cedar Stables Inn and Suites $152 per person Apr 20 - Apr 22 found 1 day ago Roundtrip flight included New York (NYC) to Cleveland (CLE) 8.8/10 Excellent! (482 reviews) The room was so nice and cozy! This was our first time staying here and we will definitely be staying again. The room was clean and they even had the good dove shampoo conditioner and soap! We love eating at the thirsty pony so being able to stay at this hotel just made our experience even better with only having a short walk down the hall to the restaurant. Reviewed on Feb 22, 2026 ![The Washington Boutique Hotel](https://images.trvl-media.com/lodging/100000000/99990000/99982700/99982661/a65e2629_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Washington Boutique Hotel Save 100% on your flight $218 per person Apr 20 - Apr 22 found 1 day ago Roundtrip flight included New York (NYC) to Cleveland (CLE) 9/10 Wonderful! (80 reviews) Cute house, neat location. Avoid the crazy neighbor. Reviewed on Oct 19, 2025 ![Anchor Bay Inn and Suites](https://images.trvl-media.com/lodging/85000000/84090000/84083600/84083550/79724d88_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Anchor Bay Inn and Suites $170 per person Apr 20 - Apr 22 found 1 day ago Roundtrip flight included New York (NYC) to Cleveland (CLE) 8.8/10 Excellent! (160 reviews) Room was very clean but the heat/ Reviewed on Oct 29, 2025 ![Great Wolf Lodge Sandusky OH](https://images.trvl-media.com/lodging/2000000/1190000/1183600/1183594/371038d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Great Wolf Lodge Sandusky OH Save 100% on your flight $180 per person Apr 20 - Apr 22 found 1 day ago Roundtrip flight included New York (NYC) to Cleveland (CLE) 8.4/10 Very Good! (1,003 reviews) The room and the entire place was excellent we really enjoyed ourselves Reviewed on Feb 28, 2026 ![Kimpton Schofield Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13190000/13181300/13181279/db78d7b4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Schofield Hotel by IHG Downtown Cleveland $536 per person Apr 24 - Apr 27 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.6/10 Excellent! (1,006 reviews) Amazing hotel in a great spot. Walking distance to rocket arena and great restaurants. Super clean and friendly staff Reviewed on Mar 1, 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/2026-04-01/2026-04-08/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CGF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6180248) ### 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 ![Best Western Plus Mentor-Cleveland Northeast](https://images.trvl-media.com/lodging/1000000/660000/660000/659951/ae24b750_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 $98 nightly $112 total Mar 15 - Mar 16 Total with taxes and fees 9.2/10 Wonderful! (1,000 reviews) Room was magnicent. Staff was great Reviewed on Feb 21, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=659951&PinnedHotelID=659951&HadPinnedHotel=true®ionId=6180248) ![The Lodge at Geneva](https://images.trvl-media.com/lodging/2000000/1380000/1372100/1372060/6c62a377_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Lodge at Geneva 4888 N. Broadway Geneva OH Fully refundableReserve now, pay when you stay $123 nightly $140 total Mar 4 - Mar 5 Total with taxes and fees 9.2/10 Wonderful! (828 reviews) One of our most favorite parts about staying at hotels is getting to enjoy free continental breakfasts and free coffee all day long. So, of course, we excitedly woke up the kids and rushed downstairs to go and enjoy the morning with a delicious breakfast. To our dismay, we discovered that breakfast ... Reviewed on Mar 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%2F2026&selected=1372060&PinnedHotelID=1372060&HadPinnedHotel=true®ionId=6180248) ![Red Roof Inn Cleveland - Mentor/ Willoughby](https://images.trvl-media.com/lodging/1000000/20000/13800/13716/dc1ee235_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 $55 nightly $64 total Mar 5 - Mar 6 Total with taxes and fees 7.4/10 Good! (1,002 reviews) The staff were good. It served our needs. Our only complaint was that it was supposed to be a non smoking room and it smelled of smoke so badly I did not have a good night's sleep Reviewed on Feb 25, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%2F2026&selected=13716&PinnedHotelID=13716&HadPinnedHotel=true®ionId=6180248) [See all 561 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F2%2F2026&endDate=3%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