Title: Visit Middletown: Best of Middletown Tourism | Expedia Travel Guide - 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) # Middletown ## Travel Guide ![Middletown](https://images.trvl-media.com/place/6164020/0a9ca11f-dcc0-4ca9-affe-11fe2516dc02.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Middletown Things to do - Middletown Hotel Deals - Vacation Rentals in Middletown ![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 $100 CA $124 total Mar 31 - Apr 1 includes taxes & fees Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Cedar ... 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 CA $108 CA $122 total Apr 5 - Apr 6 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ... 9/10 Wonderful! (1,005 reviews) The staff was extremely unpleasant to me. Reviewed on Mar 30, 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 CA $149 CA $162 total Mar 31 - Apr 1 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 9.2/10 Wonderful! (2,280 reviews) We had a quick stop for a few hour rest. We Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=12013) [See all 622 properties in Middletown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=31%2F03%2F2026&endDate=01%2F04%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. ![Falling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen!](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/4a09aa4b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Falling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen! Rileyville VA Book a stay at this family-friendly cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley ... 9.8/10 Exceptional! (308 reviews) The cabin was cozy and warm in this wintry weather. The host was easy to communicate with and everything went smoothly. Reviewed on Feb 18, 2026 [](https://expedia.ca/Rileyville-Hotels-Falling-Leaf-Cabin-Secluded-With-Mountain-View.h33748224.Hotel-Information) ![Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo](https://images.trvl-media.com/lodging/27000000/26970000/26968400/26968349/88605fc6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo Front Royal VA Stay at this cabin in Front Royal. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Glen Manor Vineyards and Shenandoah River State Park ... 9.6/10 Exceptional! (343 reviews) The space was cozy and nice. The view of the river was absolutely breathtaking from the back porch! Quiet and relaxing. Reviewed on Mar 23, 2026 [](https://expedia.ca/Winchester-Hotels-Log-Cabin-With-A-Spectacular-View-Of-The-Shenandoah-River-And-The-Massanutten-Mo.h26968349.Hotel-Information) ![Secluded River Cabin Getaway (Masten Cabin)](https://images.trvl-media.com/lodging/58000000/57920000/57914400/57914375/79bbd46a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Secluded River Cabin Getaway (Masten Cabin) Strasburg VA Stay at this vacation home in Strasburg. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Secret Passage Ranch and Strasburg Museum are located ... 9.8/10 Exceptional! (182 reviews) Very nice pet friendly cabin outside of town, yet still close enough to everything. Cabin had everything we needed for a few day getaway. Was very clean and as described. Check in process and instructions were super easy. We enjoyed our stay and 100% would stay again if we come back to the area. Reviewed on Mar 16, 2026 [](https://expedia.ca/Strasburg-Hotels-Secluded-River-Cabin-Getaway.h57914375.Hotel-Information) [See all properties in Middletown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=12013&sort=VACATION_RENTAL) 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. ## Check Middletown hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12013&startDate=2026-03-30&endDate=2026-03-31)[Mar 30 - Mar 31](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12013&startDate=2026-03-30&endDate=2026-03-31) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12013&startDate=2026-03-31&endDate=2026-04-01)[Mar 31 - Apr 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12013&startDate=2026-03-31&endDate=2026-04-01) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12013&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)[Apr 3 - Apr 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12013&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12013&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026)[Apr 10 - Apr 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12013&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026) ### Popular places to visit ![Belle Grove Plantation](https://images.trvl-media.com/place/6164020/0a9ca11f-dcc0-4ca9-affe-11fe2516dc02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Belle Grove Plantation Learn about the local history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area. [](https://expedia.ca/Belle-Grove-Plantation-Middletown.d6164020.Vacation-Attraction) #### Cedar Creek and Belle Grove National Historical Park Explore the great outdoors at Cedar Creek and Belle Grove National Historical Park, a lovely green space in Middletown. Stroll along the riverfront or experience the area's entertainment venues. [](https://expedia.ca/Cedar-Creek-And-Belle-Grove-National-Historical-Park-Middletown.d6093271.Vacation-Attraction) #### Jackson's Chase Golf Course Enjoy a round of golf in Middletown at Jackson's Chase Golf Course. Amble around this vibrant area's riverfront, or seek out the hiking trails. [](https://expedia.ca/Jacksons-Chase-Golf-Course-Middletown.d553248621532661831.Vacation-Attraction) - Cities near Middletown - Places of interest - [Shenandoah National Park ](https://expedia.ca/Shenandoah-National-Park-Virginia.d6025893.Vacation-Attraction) - [Front Royal Entrance Shenandoah National Park ](https://expedia.ca/Front-Royal-Entrance-Shenandoah-National-Park-Front-Royal.d6129961.Vacation-Attraction) - [Skyline Caverns ](https://expedia.ca/Skyline-Caverns-Front-Royal.d6093201.Vacation-Attraction) - [Naked Mountain Winery & Vineyards ](https://expedia.ca/Naked-Mountain-Winery-Vineyards-Delaplane.d553248621532661859.Vacation-Attraction)