Title: Book The Best Hotels in Middletown, VA for 2026 from CA $101 - Fully Refundable Options - Expedia.ca [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) ![Nana’s Irish Pub was a great and delicious stop off the main road on the way to Asheville, NC. Super cute redesigned bank. The bank door is still in the corner and is not a closet. Highly suggested for a pit stop!](https://images.trvl-media.com/place/12013/db58f126-7d10-4018-a689-28fc2b700f21/historic-middletown-state-bank-restaurant-interior-vault-door-brick-stained-glass.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Samantha Keyes # Find hotels in Middletown, VA from CA $101 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Middletown Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&amenities=PETS) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&lodging=CABIN) Pool [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&amenities=POOL) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&travelerType=family_friendly) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&amenities=HOT_TUB) Farm [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&lodging=AGRITOURISM) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&lodging=COTTAGE) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&lodging=APARTMENT) Chalet [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&lodging=CHALET) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-01-12&d1=2026-01-12&endDate=2026-01-14&d2=2026-01-14&amenities=WATER_PARK) ## Check prices for these dates Tonight [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-12-29&endDate=2025-12-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-12-30&endDate=2025-12-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middletown 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) ![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) ![Interior detail](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/d6942b45.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) ### Wayside Inn [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) Middletown 9.2/10 Wonderful (418) "Historic inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $98 CA $122 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/8753a03f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed with Sofa bed, Smoking](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/3c65e97c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/1c983a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/92453303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Inn & Suites Middletown - Winchester South [](https://www.expedia.ca/Middletown-Hotels-Econo-Lodge-Inn-Suites.h856310.Hotel-Information) Middletown 5.8/10 (299) "I loved staying here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Whitney CA $94 CA $104 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Middletown-Hotels-Econo-Lodge-Inn-Suites.h856310.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/c99442ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/daf3dfdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/76fedaf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TRU By Hilton Winchester [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) Winchester 9.0/10 Wonderful (778) "Clean rooms, courteous staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Holly CA $100 CA $109 total includes taxes & fees Jan 26 - Jan 27, 2026 [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/3e194222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/e8922549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) Winchester 9.2/10 Wonderful (1407) "Clean room great helpful staff good breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Loretta CA $108 CA $118 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/f8e3941a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/6a37f73c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/6a36301f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Winchester [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) Winchester 9.4/10 Exceptional (1089) "We have stayed here many times on our way to Massachusetts and find it perfect every time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patsy CA $133 CA $144 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/5e25574f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/51a72e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/cbff06a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/6b04791b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Winchester, VA [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) Winchester 8.8/10 Excellent (1002) "Have stayed here multiple times -always good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $112 CA $122 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d78ffc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) Winchester 9.2/10 Wonderful (2240) "Staff is very pleasant and personable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $135 CA $147 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/10b5cc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/325feec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/a71565c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/5e0036d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Front Royal [](https://www.expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) Front Royal 7.6/10 Good (1001) "Good condition " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phillip CA $85 CA $94 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/6b1b10e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/b2c1f0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/1687542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Winchester [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) Winchester 9.0/10 Wonderful (1003) "The place is spotless, comfortable and quiet. Very convenient as well, right off of 81" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $105 CA $119 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e37f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e90770a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Winchester [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) Winchester 9.2/10 Wonderful (1001) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaron CA $103 CA $113 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ef7d5b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/fcd1c267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/83ee60b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/71be8e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Winchester South-Stephens City by IHG [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) Stephens City 8.2/10 Very good (807) "Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rose CA $101 CA $110 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/53b7b275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/decc147c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/c9f83fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/502f6bec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Winchester near University [](https://www.expedia.ca/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) Winchester 7.8/10 Good (1001) "great stay with breakfast too" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $85 CA $92 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/19e0634f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking | Living area](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/fe05e412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/8247e5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) Winchester 8.6/10 Excellent (1080) "Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stefanie CA $93 CA $101 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/27064e98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/fb0da257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) Winchester 9.0/10 Wonderful (806) "We stay here a lot and it is always consistently clean and service is great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $127 CA $138 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Elevator](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/be9a8325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/e47a228e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9ef74ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Strasburg/Shenandoah Valley [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) Strasburg 8.2/10 Very good (1004) "Breakfast was delicious " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $100 CA $111 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/a5945e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/3c75b4dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/61e9f06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Winchester by IHG [](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information) Winchester 8.8/10 Excellent (548) "The room was just the right temp, check in with my service dog was the most professional I’ve experienced! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shenandoah CA $107 CA $116 total includes taxes & fees Jan 16 - Jan 17, 2026 [](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information) ![Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/57a6dfe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/e6dc1dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/164a5d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) Winchester 9.4/10 Exceptional (788) "Great staff, very clean room with a good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim CA $146 CA $159 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, Select Comfort beds, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/cab9baeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/5ea79918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) Winchester 9.0/10 Wonderful (923) "comfortable room, amenities and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Prashant CA $146 CA $159 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/ad5604d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/b96d495c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9874bc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) Front Royal 9.0/10 Wonderful (1001) "Friendly staff, nice clean room, hotel restaurant was delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy CA $133 CA $147 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/b6f40366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winchester Se-Historic Gateway by IHG [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) Winchester 9.0/10 Wonderful (1002) "Great room cozy bed fabulous restaurant great staff on property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joyce CA $107 CA $120 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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=2026-01-12&endDate=2026-01-13®ionId=12013&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Hotels.d12013.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Hotels.d12013.Travel-Guide-Hotels) ## Learn more about Middletown History buffs can explore the Cedar Creek Battlefield and Belle Grove Plantation, where costumed interpreters bring Civil War stories to life. Visit the Wayside Inn, Virginia's oldest continuously operating inn, and ask locals about hidden hiking trails in nearby Shenandoah Valley. [See all hotels in Middletown](https://www.expedia.ca/Hotel-Search?startDate=2026-01-12&endDate=2026-01-13&adults=2®ionId=12013) ![Nana’s Irish Pub was a great and delicious stop off the main road on the way to Asheville, NC. Super cute redesigned bank. The bank door is still in the corner and is not a closet. Highly suggested for a pit stop!](https://images.trvl-media.com/place/12013/db58f126-7d10-4018-a689-28fc2b700f21.jpg?impolicy=fcrop&w=300&h=400&p=1&q=high) Photo by Samantha Keyes ### Stay near popular Middletown attractions [](https://expedia.ca/Belle-Grove-Plantation-Hotels.0-l6164020-0.Travel-Guide-Filter-Hotels) ![Belle Grove Plantation](https://mediaim.expedia.com/destination/2/cc4669911702549b209190768b702758.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. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6164020) [](https://expedia.ca/Cedar-Creek-And-Belle-Grove-National-Historical-Park-Hotels.0-l6093271-0.Travel-Guide-Filter-Hotels) #### 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. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6093271) [](https://expedia.ca/Cedar-Creek-Battlefield-Foundation-Hotels.0-l553248621532661823-0.Travel-Guide-Filter-Hotels) #### Cedar Creek Battlefield Foundation You can find out about the history of Middletown with a visit to Cedar Creek Battlefield Foundation. Stroll along the riverfront or experience the entertainment venues in this vibrant area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532661823) [](https://expedia.ca/Wayside-Theater-Hotels.0-l6164044-0.Travel-Guide-Filter-Hotels) #### Wayside Theater Get tickets for a show at Wayside Theater, a storied theater in Middletown. Amble around this vibrant area's riverfront or experience its entertainment venues. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6164044) [](https://expedia.ca/Jacksons-Chase-Golf-Course-Hotels.0-l553248621532661831-0.Travel-Guide-Filter-Hotels) #### 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. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532661831) ## More cheap stays in Middletown ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Travelodge by Wyndham Winchester 160 Front Royal Pike Winchester VA CA $93 CA $101 total Jan 18 - Jan 19, 2026 includes taxes & fees 8.4/10 Very Good! (1,079 reviews) [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Ramada by Wyndham Strasburg/Shenandoah Valley 21 Signal Knob Dr Strasburg VA CA $100 CA $111 total Jan 5 - Jan 6, 2026 includes taxes & fees 8.2/10 Very Good! (1,004 reviews) [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza Winchester VA CA $108 CA $118 total Jan 4 - Jan 5, 2026 includes taxes & fees 9/10 Wonderful! (1,400 reviews) [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Winchester 195 Kernstown Commons Blvd Winchester VA CA $133 CA $144 total Jan 25 - Jan 26, 2026 includes taxes & fees 9.4/10 Exceptional! (1,090 reviews) [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Winchester-University/Mall Area 640 East Jubal Early Drive Winchester VA CA $139 CA $158 total Jan 4 - Jan 5, 2026 includes taxes & fees 9/10 Wonderful! (1,001 reviews) [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### SpringHill Suites by Marriott Winchester 280 MARKET STREET Winchester VA CA $146 CA $159 total Jan 4 - Jan 5, 2026 includes taxes & fees 9.4/10 Exceptional! (788 reviews) [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ## Hotels in Middletown with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 1 properties [](https://expedia.ca/5Star-Middletown-Hotels.s50-0-d12013.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 4 properties [](https://expedia.ca/4Star-Middletown-Hotels.s40-0-d12013.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 61 properties [](https://expedia.ca/3Star-Middletown-Hotels.s30-0-d12013.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 108 properties [](https://expedia.ca/2Star-Middletown-Hotels.s20-0-d12013.Travel-Guide-Filter-Hotels) ## Find out more about Middletown ### Top reasons to visit Middletown - **Outdoor Adventures:** Middletown offers stunning scenery and a variety of activities for outdoor enthusiasts, including hiking, skiing, and exploring beautiful rivers. - **Charming Atmosphere:** Experience the small-town charm with family-friendly neighbourhoods, perfect for relaxation and exploration. - **Cultural Experiences:** Discover local cultural attractions and community events that enrich your visit. - **Convenient Accommodations:** A range of welcoming options, from pet-friendly motels to business hotels, cater to all travellers. - **Nearby Attractions:** Ideal for day trips, Middletown provides easy access to local shopping centres and other exciting destinations. ### Find great hotels near Middletown Explore a range of welcoming accommodations in Middletown, Virginia, ideal for every traveller. From pet-friendly motels to business-themed hotels, you'll find options that cater to diverse needs, including LGBTQIA-friendly facilities. Whether you're seeking a cozy stay or the best hotels in town, Middletown has something to offer for everyone looking to enjoy a memorable vacation experience. - **[Travelodge by Wyndham Winchester: ](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)** Nestled 17.7km from Middletown, Travelodge by Wyndham Winchester is a charming motel that caters to pet lovers seeking a relaxed getaway. With a pet-friendly policy, guests can enjoy the convenience of travelling with their furry companions. The motel features essential amenities, ensuring a comfortable stay for all. The property’s welcoming atmosphere and emphasis on accessibility make it an ideal choice for those looking for a simple yet enjoyable lodging experience. - **Country Inn & Suites by Radisson, Winchester, VA:** Located 12.9km from Middletown, this cozy 3-star hotel offers a family-friendly atmosphere combined with excellent business amenities. Country Inn & Suites is perfect for both leisure and corporate travellers, featuring accessible business centres, meeting rooms, and a 24-hour conference space. Families can take advantage of complimentary cribs, while pets are also welcome, making it a home away from home. Guests can expect a warm environment complemented by friendly service, ensuring a memorable stay for everyone. - **[Holiday Inn Winchester Se-Historic Gateway by IHG: ](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information)** Just 17.7km from Middletown, the Holiday Inn Winchester Se-Historic Gateway stands out for its commitment to inclusivity and comfort. This 3-star hotel is LGBTQIA welcoming and provides a range of business facilities, including accessible meeting spaces and a dedicated business centre. Families will appreciate the availability of complimentary cribs, making it suitable for guests of all ages. With its modern amenities and friendly atmosphere, this hotel ensures a pleasant and accommodating experience for all visitors. ### Where to stay near Middletown Middletown, Virginia offers a delightful blend of outdoor adventures and rich history, making it an ideal vacation spot for Canadian travellers. Explore the charming small town atmosphere, with its scenic views and family-friendly neighbourhoods. Venture into the city center for a taste of urban life, while enjoying the beauty of the surrounding areas. Don't miss the colder months, when Middletown showcases its unique charm, perfect for memorable experiences. - **[Winchester: ](https://www.expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)** Located 19.3km from Middletown, Winchester is a charming city known for its rich history and outdoor adventures. Visitors can immerse themselves in the scenic beauty of nearby national parks and recreational areas. Peak tourist seasons occur in June to July and October when the area's vibrant atmosphere comes alive. Popular activities include skiing, exploring local landmarks, and enjoying the natural landscape around lakes and parks. Winchester offers a blend of education and adventure, making it an ideal spot for outdoor enthusiasts. - **[Front Royal: ](https://www.expedia.ca/Front-Royal-Hotels.d7312.Travel-Guide-Hotels)** Just 14.5km away from Middletown, Front Royal is a gateway to outdoor adventures and stunning scenery. With its peak visitor numbers in April, July, and September, this city attracts nature lovers year-round. Front Royal is perfect for those looking to explore national parks and recreational areas, or enjoy skiing in the winter months. The town’s proximity to numerous parks enhances the travel experience, providing ample opportunities for hiking, picnicking, and enjoying the great outdoors. - **[Strasburg: ](https://www.expedia.ca/Strasburg-Hotels.d55195.Travel-Guide-Hotels)** Situated a mere 8.0km from Middletown, Strasburg is a delightful city that captures the essence of outdoor adventure. With peak arrivals in June to August, it offers visitors a chance to embrace the beauty of nature. Activities such as skiing and exploring recreational areas are popular here, set against the backdrop of national parks and tranquil parks. Strasburg’s close-knit community and scenic landscapes make it a perfect stop for anyone looking to unwind and experience the great outdoors. ### Things to do in and around Middletown Middletown, Virginia, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and various activities. Visitors can enjoy recreational areas, educational experiences, and even skiing. For day trips, explore nearby attractions and local shopping centres, making it an ideal destination for a well-rounded vacation. Whether you're seeking relaxation or adventure, Middletown has something to offer everyone. **Shopping** In Middletown, visit [Shen-Val Farm Market](https://www.expedia.ca/Shen-Val-Farm-Market-Hotels.0-l553248621532661836-0.Travel-Guide-Filter-Hotels) for local produce and unique gifts, only 12.9km away. [Natural Art Garden Center](https://www.expedia.ca/Natural-Art-Garden-Center-Hotels.0-l553248621532661807-0.Travel-Guide-Filter-Hotels), 14.5km from town, offers beautiful plants and garden decor. If you're up for a drive, check out [Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels), located 17.7km away, for a wider shopping selection. **Recreation** At [Jackson's Chase Golf Course](https://www.expedia.ca/Jacksons-Chase-Golf-Course-Hotels.0-l553248621532661831-0.Travel-Guide-Filter-Hotels), enjoy a round of golf amidst scenic landscapes, perfect for sports enthusiasts. Just 9.7km away, [Blue Ridge Shadows Golf Club](https://www.expedia.ca/Blue-Ridge-Shadows-Golf-Club-Hotels.0-l553248621532661832-0.Travel-Guide-Filter-Hotels) offers a similar outdoor experience. For wellness, visit [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Hotels.0-l553248621587477489-0.Travel-Guide-Filter-Hotels), 11.3km from Middletown, where relaxation and rejuvenation await. **Adventure** Embark on the [Dickey Ridge Trail](https://www.expedia.ca/Dickey-Ridge-Trail-Hotels.0-l553248621532661824-0.Travel-Guide-Filter-Hotels), a scenic hiking experience located 19.3km from Middletown, perfect for outdoor enthusiasts. For adrenaline seekers, the [Summit Point Motorsports Park](https://www.expedia.ca/Summit-Point-Motorsports-Park-Hotels.0-l6164103-0.Travel-Guide-Filter-Hotels), 35.4km away, offers thrilling motor racing. Alternatively, enjoy family-friendly adventures at [Watermelon Park Campground](https://www.expedia.ca/Watermelon-Park-Campground-Hotels.0-l553248621532661928-0.Travel-Guide-Filter-Hotels), situated 30.6km from town. **Nightlife** Experience the vibrant nightlife in Middletown by catching a show at the [Wayside Theater](https://www.expedia.ca/Wayside-Theater-Hotels.0-l6164044-0.Travel-Guide-Filter-Hotels), where culture and entertainment thrive. For a bit more adventure, head to the [Bright Box Theater](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) or [Winchester Little Theater](https://www.expedia.ca/Winchester-Little-Theater-Hotels.0-l6164047-0.Travel-Guide-Filter-Hotels), both offering captivating performances just a short drive away. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Middletown To save money during your trip to Middletown, Virginia, consider visiting between December and February, when accommodation prices are lower. Tuesdays are the most affordable days to stay, while Saturdays are the priciest. Use Expedia to refine your preferences and find eco-friendly hotels, sorting by price for the best deals. You can also save by bundling your hotel, flights, and activities into one package. Exploring local parks and attractions can offer free or low-cost activities, making your vacation enjoyable without breaking the bank. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Middletown are December to February, where the prices are slightly lower. This is in comparison to May to June and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Middletown is Tuesday. The most expensive day to stay in Middletown is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your Middletown hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions in and around Middletown Middletown, Virginia, is an ideal destination for those seeking outdoor adventures and scenic beauty. Visitors can explore various points of interest, including local visitor centres and the beautiful rivers in the area. This charming town offers cultural experiences and family-friendly activities, ensuring a memorable vacation for all types of travellers looking to immerse themselves in nature and community. - **[Shenandoah River: ](https://www.expedia.ca/Shenandoah-River-Hotels.0-l681974697590321152-0.Travel-Guide-Filter-Hotels)** Experience the serene beauty of the Shenandoah River, located a mere 12.9km from Middletown. Enjoy stunning scenery and outdoor activities like kayaking, fishing, or leisurely picnicking along the banks, making it perfect for nature lovers. - **[Front Royal Entrance Shenandoah National Park: ](https://www.expedia.ca/Front-Royal-Entrance-Shenandoah-National-Park-Hotels.0-l6129961-0.Travel-Guide-Filter-Hotels)** Just 16.1km away, this visitor centre offers a gateway to adventure in Shenandoah National Park. Families can explore hiking trails, scenic views, and wildlife encounters, making it an ideal spot for outdoor enthusiasts. - **[Cedar Creek Battlefield Foundation: ](https://www.expedia.ca/Cedar-Creek-Battlefield-Foundation-Hotels.0-l553248621532661823-0.Travel-Guide-Filter-Hotels)** Situated in Middletown, this historic site immerses visitors in the rich culture and history of the Civil War. Explore informative exhibits and guided tours that bring the past to life. ### Best time to go to Middletown The best time to visit Middletown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Middletown falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Middletown falls in January, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 31.5°F (-0.3°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 35.1°F (1.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 42.6°F (5.9°C) | Light Rain | Mostly Sunny | Average | Average | | April | 53.2°F (11.8°C) | Light Rain | Mostly Sunny | Average | Average | | May | 62.6°F (17.0°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 70.9°F (21.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 75.7°F (24.3°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | Average | Average | | September | 66.7°F (19.3°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 55.6°F (13.1°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 43.3°F (6.3°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 36.7°F (2.6°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Middletown When visiting Middletown, Virginia, you can fly into two major airports. Washington Dulles International Airport ([IAD](https://www.expedia.ca/Washington-Dulles-Intl-Airport-Hotels.0-aIAD-0.Travel-Guide-Filter-Hotels)) is situated 72.4km away. Nearby hotel options include the 4-star [Hyatt Regency Dulles](https://www.expedia.ca/Herndon-Hotels-Hyatt-Regency-Dulles.h150.Hotel-Information), located 1.6km from the airport, as well as the [Hilton Washington Dulles Airport](https://www.expedia.ca/Herndon-Hotels-Hilton-Washington-Dulles-Airport.h27218.Hotel-Information), which is 3.2km away. Eastern West Virginia Regional Airport (MRB) is 48.3km from Middletown, with accommodations like the 4-star [Hillbrook Inn](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) and the 3-star [Home2 Suites by Hilton Martinsburg](https://www.expedia.ca/Martinsburg-Hotels-Home2-Suites-By-Hilton-Martinsburg.h57604643.Hotel-Information), both situated approximately 11.6kms and 4.8km from the airport, respectively. Each hotel offers convenient access to its respective airport, ensuring a smooth start to your vacation. ## Recent reviews of Middletown hotels ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 5/5 Excellent "Everything was great" A verified traveller stayed at La Quinta Inn & Suites by Wyndham Winchester Posted 10 hours ago [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 5/5 Excellent "Clean, quiet and convenient " A verified traveller stayed at Ramada by Wyndham Strasburg/Shenandoah Valley Posted 11 hours ago [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![TRU By Hilton Winchester](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg) ### TRU By Hilton Winchester 5/5 Excellent "Clean rooms, courteous staff" A verified traveller stayed at TRU By Hilton Winchester Posted 2 days ago [](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 5/5 Excellent "All of the above mentioned and a great, nutritious and varied breakfast. Also, both regular and decaf coffee were available in the breakfast area whenever I wanted it. Lastly, plentiful parking." A verified traveller stayed at Travelodge by Wyndham Winchester Posted 2 days ago [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/53b7b275_y.jpg) ### Sleep Inn & Suites Winchester near University 5/5 Excellent "Checked in 11pm. The staff were welcoming and friendly. Room is clean. Breakfast was simple but sufficient. " A verified traveller from Salt Lake City stayed at Sleep Inn & Suites Winchester near University Posted 5 days ago [](https://expedia.ca/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 5/5 Excellent "My go to when visiting my parents. No frills, great price. Clean, decent coffee and breakfast (what you expect for the price) nice gym. Rooms are quiet. Bed comfortable and super easy parking. " A verified traveller stayed at Microtel Inn & Suites by Wyndham Winchester Posted 5 days ago [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Holiday Inn Express Woodstock-Shenandoah Valley by IHG](https://images.trvl-media.com/lodging/1000000/30000/20600/20598/e45798f9_y.jpg) ### Holiday Inn Express Woodstock-Shenandoah Valley by IHG 5/5 Excellent "Very nice stay" A verified traveller stayed at Holiday Inn Express Woodstock-Shenandoah Valley by IHG Posted 6 days ago [](https://expedia.ca/Luray-Hotels-Holiday-Inn-Express-Woodstock-Shenandoah-Valley.h20598.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 5/5 Excellent "Very nice hotel for an overnight stop on way north. Right next to I-81 so we asked for (and received) a room on the parking lot side. Clean and comfortable room, but be sure to unfold the pillows before trying to sleep! Definitely recommend the nearby Bruster's Real Ice Cream for a treat, and the Sclafani's New York Bagels and Bread for breakfast!" A verified traveller stayed at Comfort Inn & Suites Winchester Posted 6 days ago [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg) ### SpringHill Suites by Marriott Winchester 5/5 Excellent "Great location, clean, safe, plenty of free parking and quiet, comfortable and spacious room." A verified traveller stayed at SpringHill Suites by Marriott Winchester Posted 7 days ago [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Middletown that travellers recommend? ### What are the best family hotels in Middletown? ### What are the top pet-friendly hotels in Middletown? ### What are the best budget hotels in Middletown? ### What are the most romantic hotels in Middletown for couples? ### When is the best time to go to Middletown? > As you navigate through the peak season, which runs from June to August, you'll find the streets bustling with tourists and locals alike. This energetic vibe is superb for those who relish in sightseeing and outdoor pursuits. The warm weather makes it an ideal time for leisurely strolls along the scenic parks, waterfronts, or bike rides through the picturesque countryside surrounding Middletown. > > > For couples looking for a romantic escape or families seeking fun-filled days, July offers the superb backdrop. The long days allow for extended adventures, whether you're picnicking by the river or enjoying a sunset cruise. Many restaurants also feature outdoor seating, enhancing your dining experience with lovely views and fresh air. > > > If you're considering a visit that aligns with a more budget-friendly approach, September can be a fantastic alternative. While the summer crowds begin to dwindle, the pleasant weather continues, making it a great time for outdoor activities and sightseeing without the busyness of peak season. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Middletown hotel booking with Expedia? ### How much is the nightly rate at a Middletown hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [4 Star Hotels in Stephens City ](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall ](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Hotels near Blue Ridge Shadows Golf Club ](https://www.expedia.ca/Blue-Ridge-Shadows-Golf-Club-Hotels.0-l553248621532661832-0.Travel-Guide-Filter-Hotels) - [Hotels near Bright Box Theater ](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) - [B&B in College Park ](https://www.expedia.ca/College-Park-Bed-And-Breakfast.d553248635975870482-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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