Title: Middletown Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d12013.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d12013.Travel-Guide-VacationRentals)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d12013.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6164020/0a9ca11f-dcc0-4ca9-affe-11fe2516dc02.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Middletown Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Stephanie Sutton - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 Middletown Vacation Let our vacation packages to Middletown inspire your next escape. You'll find a whole lot to like about this vibrant city, starting with the neighborhood of Shawnee Land, which is good for hiking and nature. Any trip to Middletown needs a well-thought-out itinerary. Fill yours with leading attractions like [Jacksons Chase Golf Course](https://www.expedia.ca/Jacksons-Chase-Golf-Course-Middletown.d553248621532661831.Vacation-Attraction), [Blue Ridge Shadows Golf Club](https://www.expedia.ca/Blue-Ridge-Shadows-Golf-Club-Front-Royal.d553248621532661832.Vacation-Attraction) and [Belle Grove Plantation](https://www.expedia.ca/Belle-Grove-Plantation-Middletown.d6164020.Vacation-Attraction). Don't put off exploring this destination any longer. Your ultimate Middletown vacation is a few clicks away with Expedia. ## Ready to book your vacation to Middletown? Choose your dates ## Middletown Hotel Deals ![Wayside Inn](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/a3d72fc4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wayside Inn 7783 Main St Middletown VA CA $99 CA $124 total Mar 31 - Apr 1 includes taxes & fees 9.2/10 Wonderful! (426 reviews) Nostalgia and history are prime attractions of this lovely inn. The barkeep Justin was friendly and helpful Reviewed on Mar 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=34467&PinnedHotelID=34467&HadPinnedHotel=true®ionId=12013) ![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Winchester Se-Historic Gateway by IHG 333 Front Royal Pike Winchester VA Fully refundable CA $122 CA $137 total Apr 5 - Apr 6 includes taxes & fees 9/10 Wonderful! (1,000 reviews) Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=1889084&PinnedHotelID=1889084&HadPinnedHotel=true®ionId=12013) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Winchester 1055 Millwood Pike, Route 50 East Winchester VA Fully refundableReserve now, pay when you stay CA $148 CA $161 total Mar 29 - Mar 30 includes taxes & fees 9.2/10 Wonderful! (2,271 reviews) Very nice would stay there again Reviewed on Mar 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=12013) [See all 622 properties in Middletown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%2F03%2F2026®ionId=12013) 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. ![](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 [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. 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 on select hotels and earn double points 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