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 ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_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 $134 CA $146 total Feb 8 - Feb 9 includes taxes & fees 9.2/10 Wonderful! (2,259 reviews) Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience. Reviewed on Jan 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=12013) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Travelodge by Wyndham Winchester 160 Front Royal Pike Winchester VA Fully refundableReserve now, pay when you stay CA $96 CA $104 total Feb 8 - Feb 9 includes taxes & fees 8.4/10 Very Good! (1,076 reviews) Clean place, breakfast ok, warm and comfy, would stay again Reviewed on Jan 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=9600&PinnedHotelID=9600&HadPinnedHotel=true®ionId=12013) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The George Washington Hotel, A Wyndham Grand Hotel 103 E Piccadilly St Winchester VA Fully refundableReserve now, pay when you stay CA $173 CA $196 total Feb 17 - Feb 18 includes taxes & fees 9.2/10 Wonderful! (1,000 reviews) Clean nice room Great location for restaurants Reviewed on Jan 28, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true®ionId=12013) [See all 631 properties in Middletown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%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