Title: Book the Best Middletown LUXURY Hotels - Upscale Hotels in Middletown, VA | 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)[Middletown Vacation Packages](https://expedia.ca/Middletown.d12013.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/cc4669911702549b209190768b702758.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Stephanie Sutton # Find luxury hotels in Middletown, VA ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Middletown Luxury Hotels Tonight [Sep 26 - Sep 27](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-09-26&endDate=2025-09-27&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-09-27&endDate=2025-09-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-09-26&endDate=2025-09-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middletown Luxury Hotels ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/299522c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/06bbe3a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/b112d555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/2f175422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wayside Inn Middletown 9.2/10 Wonderful (406) "Rooms and property were beautiful. Wish they provided garbage cans and ash trays for outdoor seating. " CA $128 CA $156 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-10&endDate=2025-10-11®ionId=12013&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Middletown Hotel Reviews ![The George Washington Hotel, A Wyndham Grand Hotel](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool is a spectacle to behold! The beauty along with the perfect water temperature provided a perfect ending to our evening!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "This location has to be one of the best hotels I have ever stayed in. Very very clean, friendly people and a super good breakfast. They actually had someone restocking the breakfast bar. Pet friendly too. Very convenient access on and off the highway at a very reasonable rate for the night. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Clean, spacious, comfy, nice staff." [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Clean room" [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Spark by Hilton Winchester](//images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89_y.jpg) ### Spark by Hilton Winchester 10/10 Excellent "The staff was very friendly. The room was clean. They supplied enough towels. The breakfast bar had variety. It was quiet for us, but we had a 2 year old that is very boisterous and likes to dance so I don't know if that bothered anyone around us or below us." [](https://expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![Wayside Inn](//images.trvl-media.com/lodging/1000000/40000/34500/34467/299522c8_y.jpg) ### Wayside Inn 10/10 Excellent "What a lovely place. We spent a night here, and the facility was historic and beautiful. Our room was clean and comfortable. The staff could not have been kinder and more welcoming. We really enjoyed talking with them about the history of the area. I hope we can stay here again!!" [](https://expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your stay in Middletown? > Use Expedia to arrange your flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport, and then choose from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to get what you want to make your stay special. If you want an upscale hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Middletown offers. During your visit, you might want to enjoy the restaurants and bars which Middletown is known for. ### When can I expect good weather in Middletown? > Planning for the weather is a good way to make your trip to Middletown relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Middletown is 43 inches. ### What's there to see and do in Middletown? > Enjoy Middletown and visit Cedar Creek and Belle Grove National Historical Park, Cedar Creek Battlefield Foundation, and Belle Grove Plantation. 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