Title: Visit Middletown: 2026 Travel Guide for Middletown, Maryland | Expedia.com [Hotels in Middletown](https://expedia.com/Middletown-Hotels.d6351200.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.com/Middletown-Vacation-Rentals.d6351200.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.com/Cheap-Flights-To-Middletown.d6351200.Travel-Guide-Flights)[Car Rentals in Middletown](https://expedia.com/Car-Rentals-In-Middletown.d6351200.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.com/Middletown.d6351200.Destination-Travel-Guides) # Middletown, MD ## Travel Guide ![Washington Monument](https://images.trvl-media.com/place/6351200/c824f6fe-887c-4c10-9f1a-99abbb2720b8.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Gathland state park. ](https://images.trvl-media.com/place/553248621532662503/06187189-41f8-4204-b46c-3c682c44b7bd.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![The first Washington Monument, near Boonsboro, Maryland.](https://images.trvl-media.com/place/553248621532662508/ca71cfc3-4c8d-4995-81f5-dfcbb0951c16.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Built in 1827 by a group of local citizens, using rock quarried from the site. This is the first Monument dedicated to George Washington. ](https://images.trvl-media.com/place/6351200/69e1bbd9-466b-4e74-8b7d-50fc2b2bff0d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Middletown Things to do - Middletown Hotel Deals - Vacation Rentals in Middletown ![Countryside Cabin with Mountain Views near Surreybrooke Gardens](https://images.trvl-media.com/lodging/81000000/80240000/80238900/80238842/dc116b78_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Countryside Cabin with Mountain Views near Surreybrooke Gardens Middletown MD Stay at this cabin in Middletown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Maryland National Golf Club and Orchid Cellar Winery ... 10/10 Exceptional! (133 reviews) We absolutely loved our stay & hope to return! So charming & peaceful. Close enough to dining, shopping, & historic sites. Reviewed on Feb 19, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=80238842&PinnedHotelID=80238842&HadPinnedHotel=true®ionId=6351200) [](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=80238842&PinnedHotelID=80238842&HadPinnedHotel=true®ionId=6351200) ![Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.](https://images.trvl-media.com/lodging/37000000/36390000/36380300/36380283/72598aee_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location. Middletown MD $234 nightly $248 total Apr 1 - Apr 2 Total with taxes and fees Stay at this cabin in Middletown. Enjoy laundry facilities, an in-room coffeemaker, and in-room fireplaces. Popular attractions Orchid Cellar Winery and Willow ... 9.6/10 Exceptional! (111 reviews) Good stay. Would visit again. Reviewed on Jan 11, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=36380283&PinnedHotelID=36380283&HadPinnedHotel=true®ionId=6351200) ![Country Inn & Suites by Radisson, Frederick, MD](https://images.trvl-media.com/lodging/1000000/60000/59600/59588/1aff68d6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Frederick, MD 5579 Spectrum Dr Frederick MD $84 nightly $93 total Apr 12 - Apr 13 Total with taxes and fees Book a stay at this business-friendly hotel in Frederick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 8.2/10 Very Good! (1,276 reviews) Breakfast was very good. Cleanliness superb. Reviewed on Mar 21, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=59588&PinnedHotelID=59588&HadPinnedHotel=true®ionId=6351200) [See all 811 properties in Middletown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F24%2F2026&endDate=3%2F25%2F2026®ionId=6351200) 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. ![Countryside Cabin with Mountain Views near Surreybrooke Gardens](https://images.trvl-media.com/lodging/81000000/80240000/80238900/80238842/dc116b78_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Countryside Cabin with Mountain Views near Surreybrooke Gardens Middletown MD Stay at this cabin in Middletown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Maryland National Golf Club and Orchid Cellar Winery ... 10/10 Exceptional! (133 reviews) We absolutely loved our stay & hope to return! So charming & peaceful. Close enough to dining, shopping, & historic sites. Reviewed on Feb 19, 2026 [](https://expedia.com/Middletown-Hotels-Countryside-Cabin-With-Mountain-Views-Near-Surreybrooke-Gardens.h80238842.Hotel-Information) ![Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.](https://images.trvl-media.com/lodging/37000000/36390000/36380300/36380283/72598aee_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location. Middletown MD Stay at this cabin in Middletown. Enjoy laundry facilities, an in-room coffeemaker, and in-room fireplaces. Popular attractions Orchid Cellar Winery and Willow ... 9.6/10 Exceptional! (111 reviews) Good stay. Would visit again. Reviewed on Jan 11, 2026 [](https://expedia.com/Frederick-Hotels-Vintage-Cabin-In-The-Of-Middletown.h36380283.Hotel-Information) ![Charming "Cream of the Crop" Cape ~❤️of Middletown](https://images.trvl-media.com/lodging/43000000/42350000/42342000/42341954/da4a4dbd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Charming "Cream of the Crop" Cape \~❤️of Middletown Middletown MD Stay at this vacation home in Middletown. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Orchid Cellar Winery and Willow Oaks ... 10/10 Exceptional! (143 reviews) An absolutely charming getaway spot tucked in a small town with trendy shops and eateries. Our host gave fabulous recommendations and the property was spotless, cozy and well equipped for the perfect weekend getaway. Reviewed on Mar 8, 2026 [](https://expedia.com/Frederick-Hotels-Vrbo-Property.h42341954.Hotel-Information) [See all properties in Middletown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6351200&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.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6351200&startDate=2026-03-23&endDate=2026-03-24)[Mar 23 - Mar 24](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6351200&startDate=2026-03-23&endDate=2026-03-24) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6351200&startDate=2026-03-24&endDate=2026-03-25)[Mar 24 - Mar 25](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6351200&startDate=2026-03-24&endDate=2026-03-25) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6351200&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6351200&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6351200&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6351200&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026) ### Popular places to visit #### Maryland National Golf Club Enjoy a round of golf in Middletown at Maryland National Golf Club. Discover the coffeehouses and its festivals while you're in the area. [](https://expedia.com/Maryland-National-Golf-Club-Middletown.d553248621532662573.Vacation-Attraction) #### Willow Oaks Craft Cider and Wine You can enjoy a tasting or tour at Willow Oaks Craft Cider and Wine during your travels to Middletown. Amble around the area's riverfront or experience its entertainment venues. [](https://expedia.com/Willow-Oaks-Craft-Cider-And-Wine-Middletown.d873858366439686144.Vacation-Attraction) #### Orchid Cellar Winery You can enjoy a tasting or tour at Orchid Cellar Winery during your travels to Middletown. Discover the area's festivals, or seek out its golf courses. [](https://expedia.com/Orchid-Cellar-Winery-Middletown.d553248621532662572.Vacation-Attraction) ## Cities near Middletown ![Gathland state park. ](https://images.trvl-media.com/place/553248621532662503/06187189-41f8-4204-b46c-3c682c44b7bd.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Jefferson ![Frederick](https://images.trvl-media.com/place/6057476/762ddbae-d287-42f6-bf6d-346b7adb887b.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Frederick ![I almost got blown off this mountain trying to take this picture, super windy! lol](https://images.trvl-media.com/place/3000347942/f4ab36f9-40d7-41d3-8600-51f834ea4bb5.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Myersville ![Gathland state park. ](https://images.trvl-media.com/place/553248621532662503/06187189-41f8-4204-b46c-3c682c44b7bd.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Rohrersville ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Orchid Cellar Winery ](https://www.expedia.com/Orchid-Cellar-Winery-Hotels.0-l553248621532662572-0.Travel-Guide-Filter-Hotels) - 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[Washington Monument State Park ](https://www.expedia.com/Washington-Monument-State-Park-Maryland.d553248621532662508.Vacation-Attraction) - [Visit Rohrersville ](https://www.expedia.com/Rohrersville.dx3000347978) - [Visit Gapland ](https://www.expedia.com/Gapland.dx3000440648) - [Big Cork Vineyards ](https://www.expedia.com/Big-Cork-Vineyards-Rohrersville.d553248635975667708.Vacation-Attraction) - [Fort Detrick ](https://www.expedia.com/Fort-Detrick-Frederick.d553248635950238695.Vacation-Attraction) - [Schifferstadt ](https://www.expedia.com/Schifferstadt-Frederick.d553248621532662582.Vacation-Attraction) - [Visit Boonsboro ](https://www.expedia.com/Boonsboro.dx3000440431) - [Gapland Vacations ](https://www.expedia.com/Gapland.d3000440648.Destination-Travel-Guides) - [Visit Frederick ](https://www.expedia.com/Frederick.dx6057476) - [Baker Park ](https://www.expedia.com/Baker-Park-Frederick.d553248621532662578.Vacation-Attraction) - [Frederick Memorial Hospital ](https://www.expedia.com/Frederick-Memorial-Hospital-Frederick.d553248635943352150.Vacation-Attraction) - 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