Title: Book The Best Hotels in Middletown, VA for 2025 from CA $90 - Compare prices by date | 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.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Samantha Keyes # Find hotels in Middletown, VA from CA $90 ![](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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&lodging=CABIN) 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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&lodging=COTTAGE) 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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=HOT_TUB) 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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&lodging=APARTMENT) 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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=POOL) ## Check prices for these dates Tonight [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-10-10&endDate=2025-10-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 622 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Breakfast area](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/8753a03f.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) ![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) ![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 5.8/10 (289) "I loved staying here!" CA $95 CA $104 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Middletown-Hotels-Econo-Lodge-Inn-Suites.h856310.Hotel-Information) ![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) ![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) ![Interior detail](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/d6942b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wayside Inn Middletown 9.2/10 Wonderful (407) "Clean room and friendly staff. Air conditioning was very noisy and the inn needs some upkeep, but we would stay there again." CA $156 CA $187 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel Old Town Winchester 9.4/10 Exceptional (1013) "Very nice hotel " CA $178 CA $201 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20600/20598/e45798f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Accessible, Jetted Tub](https://images.trvl-media.com/lodging/1000000/30000/20600/20598/35f36f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/30000/20600/20598/d67c8cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/20600/20598/064fbf82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Woodstock-Shenandoah Valley by IHG Woodstock 9.0/10 Wonderful (1006) "Very clean room, good breakfast and English speaking staff " CA $140 CA $157 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Luray-Hotels-Holiday-Inn-Express-Woodstock-Shenandoah-Valley.h20598.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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.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) ### La Quinta Inn & Suites by Wyndham Winchester Winchester 9.2/10 Wonderful (2178) "Great location." CA $143 CA $156 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3025100/3025089/53fbbcfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3025100/3025089/84eb785d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/4000000/3030000/3025100/3025089/79c45bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3030000/3025100/3025089/2a5460b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Woodstock, VA Woodstock 8.8/10 Excellent (1003) "Loved our stay" CA $146 CA $164 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Luray-Hotels-Hampton-Inn-Suites-Woodstock.h3025089.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/2000000/1250000/1246400/1246311/9fcf0199.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) ![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 Strasburg 8.4/10 Very good (1015) "The property was easy on and off Rt81. Staff was friendly and helpful. Rooms were clean and the restaurant attached was excellent." CA $104 CA $115 total includes taxes & fees Nov 2 - Nov 3 [](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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/69d352d9.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) ![Breakfast meal](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/a5945e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Winchester by IHG Winchester 8.8/10 Excellent (516) "The suites we're clean and spacious. The perfect stay for a family weekend!" CA $115 CA $125 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/330000/327400/327388/495de11d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/330000/327400/327388/0b7aeff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/330000/327400/327388/66fe56c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/330000/327400/327388/e12d4d7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Woodstock Shenandoah Woodstock 8.8/10 Excellent (1007) "Good overnight stay " CA $138 CA $154 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Luray-Hotels-Comfort-Inn-Woodstock-Shenandoah.h327388.Hotel-Information) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds, Smoking](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/65ba6c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/w3000h1997x0y0-2ca33d0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/422ace16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Winchester Winchester 8.6/10 Excellent (1079) "Excellent staff" CA $97 CA $105 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.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) ![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.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 Winchester 9.0/10 Wonderful (1007) "Great stay value" CA $109 CA $123 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/7e51069b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Winchester Winchester 9.2/10 Wonderful (1004) "We will be staying there again" CA $109 CA $119 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/071235b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/a2451115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/ff7a3bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/f4004e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Front Royal Near Shenandoah National Park Front Royal 6.4/10 (891) "nice for a great stay!!" CA $81 CA $90 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/a888dfb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/769f9c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/800932de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester-University/Mall Area Winchester 9.0/10 Wonderful (1016) "Staff was excellent !!! Hotel was clean and comfortable in great location !!! Would stay here again !!! " CA $160 CA $181 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/689131eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a948cd9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily breakfast for a fee](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a36008d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/037b096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Winchester Winchester 8.8/10 Excellent (496) "Great hotel" CA $134 CA $152 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b20fa3f2.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 Winchester 9.0/10 Wonderful (775) "Super friendly staff, clean rooms, very convenient. I would definitely stay here again. " CA $130 CA $141 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9cf3d079.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) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows Front Royal 9.0/10 Wonderful (1004) "Nice property and great location. " CA $160 CA $180 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.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/2000000/1500000/1497900/1497898/723a3b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Winchester Winchester 8.8/10 Excellent (884) " Nice hotel" CA $142 CA $154 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.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) ![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) ![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) ### TRU By Hilton Winchester Winchester 9.0/10 Wonderful (712) "Professional, efficient staff at check in. Hot, premium coffee always available. Clean and comfortable facilities." CA $135 CA $146 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/b2c1f0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/9fc99c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Winchester Winchester 9.0/10 Wonderful (1004) "Clean room, easy check-in, restaurants within short walking distance" CA $121 CA $137 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.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=2025-10-24&endDate=2025-10-25®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=2025-10-24&endDate=2025-10-25&adults=2®ionId=12013) ![](https://mediaim.expedia.com/destination/2/cc4669911702549b209190768b702758.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high) Photo by Stephanie Sutton ### 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-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/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/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) [](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) ## More cheap stays in Middletown ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Travelodge by Wyndham Winchester 160 Front Royal Pike, Winchester, VA CA $97 CA $105 total Oct 12 - Oct 13 includes taxes & fees 8.4/10 Very Good! (1,078 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, GPS: 35 Brandy court, Strasburg, VA CA $104 CA $115 total Nov 2 - Nov 3 includes taxes & fees 8.2/10 Very Good! (1,010 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 $113 CA $123 total Nov 9 - Nov 10 includes taxes & fees 9/10 Wonderful! (1,336 reviews) [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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 $160 CA $181 total Oct 26 - Oct 27 includes taxes & fees 9/10 Wonderful! (1,016 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 $156 CA $170 total Nov 2 - Nov 3 includes taxes & fees 9.4/10 Exceptional! (736 reviews) [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.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 $145 CA $158 total Nov 9 - Nov 10 includes taxes & fees 9.4/10 Exceptional! (1,015 reviews) [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ## Hotels in Middletown with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/19000000/18620000/18615900/18615848/76ff6888_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/2000000/1890000/1889100/1889081/204cbf3a_w.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/3000000/2680000/2678600/2678524/3336c7bb_w.jpg) 3 Star Hotels 60 properties [](https://expedia.ca/3Star-Middletown-Hotels.s30-0-d12013.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_w.jpg) 2 Star Hotels 90 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 ![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 5/5 Excellent "Great stay! Would definitely would stay again!" A verified traveller stayed at Hampton Inn Winchester-University/Mall Area Posted 5 hours ago [](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 5/5 Excellent "I love this place. Very clean. I've been to many motels in the area and they are horrible, filthy, unkempt properties. Here they have an elevator which is very easy on the legs and arms when getting one's luggage in. Very congenial owner. They don't discriminate against smokers. Other motels in the area put a smoker in rooms that weren't even cleaned. I would recommend this Travel Lodge to all types of guests. Business or leisure." A verified traveller stayed at Travelodge by Wyndham Winchester Posted 1 day ago [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 5/5 Excellent "Perfect stop over on our road trip. Clean with friendly staff. Breakfast was great with waffle machines!" A verified traveller stayed at Country Inn & Suites by Radisson, Winchester, VA Posted 2 days ago [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](//images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 5/5 Excellent "The room was perfect for a one night stay while passing through the area. The room was clean, the bed was comfortable and the location was convenient. Check in was fast and easy." A verified traveller stayed at Ramada by Wyndham Strasburg/Shenandoah Valley Posted 3 days ago [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![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 5/5 Excellent "2 blocks from city hall/old town. Got married at city hall. Very easy and accessible and the hotel was beautiful. " A verified traveller stayed at The George Washington Hotel, A Wyndham Grand Hotel Posted 4 days ago [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![SpringHill Suites by Marriott Winchester](//images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg) ### SpringHill Suites by Marriott Winchester 5/5 Excellent "Convenient " A verified traveller stayed at SpringHill Suites by Marriott Winchester Posted 4 days ago [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.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 5/5 Excellent "Great location." A verified traveller stayed at La Quinta Inn & Suites by Wyndham Winchester Posted 4 days ago [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/75c26333_y.jpg) ### Hampton Inn Front Royal 5/5 Excellent "Friendly staff and good breakfast. " A verified traveller stayed at Hampton Inn Front Royal Posted 4 days ago [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 5/5 Excellent "Clean place good price" A verified traveller stayed at Microtel Inn & Suites by Wyndham Winchester Posted 4 days ago [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Middletown that travellers recommend? > [Wayside Inn](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) stands out as a top choice for travellers seeking a great experience in Middletown, boasting a great rating of 9.2. This charming hotel offers an array of amenities that cater to various needs, making it a superb getaway for couples looking to rekindle romance or celebrate special occasions. With its exquisite couples dining options and lively evening entertainment, guests can enjoy intimate moments while savoring delicious meals. ### What are the best family hotels in Middletown? > [Wayside Inn](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) in Middletown, Virginia, is a charming family-friendly hotel that has earned an excellent review score of 9.2 from travellers. This delightful inn goes above and beyond to cater to families, offering amenities like complimentary rollaway beds and highchairs, ensuring that even the littlest guests are well cared for. Find more [child-friendly accommodations in Middletown](https://www.expedia.ca/Middletown-Hotels-Family-Hotel.0-0-d12013-tFamilyHotel.Travel-Guide-Filter-Hotels). ### What are the top pet-friendly hotels in Middletown? > [Wayside Inn](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information), a charming historic property situated in Middletown, VA, is a top choice for travellers who wish to bring their furry friends along for the adventure. With a customer review rating of 9.2, guests rave about the attentive service and friendly setting that make for a stress-free stay. See more [pet-friendly hotels in Middletown](https://www.expedia.ca/Middletown-Hotels-Pet-Friendly-Hotel.0-0-d12013-tPetFriendlyHotel.Travel-Guide-Filter-Hotels). ### What are the best budget hotels in Middletown? > The [Wayside Inn](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information), a charming historic-style hotel in Middletown, VA, is an excellent choice for budget-conscious travellers seeking quality and convenience. With an impressive guest review rating of 9.2, it offers a warm atmosphere combined with thoughtful amenities that cater to both families and couples alike. View all [budget hotels in Middletown](https://www.expedia.ca/Middletown-Hotels-Cheap-Hotels.0-0-d12013-tCheapHotels.Travel-Guide-Filter-Hotels). ### What are the most romantic hotels in Middletown for couples? > For a romantic escape, the [Wayside Inn](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) in Middletown, VA, is a delightful choice, boasting a stellar review score of 9.2. This charming hotel captures the essence of romance with its historic property design and cozy atmosphere, making it a superb retreat for couples. See all [romantic hotels in Middletown](https://www.expedia.ca/Middletown-Hotels-Romantic-Hotel.0-0-d12013-tRomanticHotel.Travel-Guide-Filter-Hotels). ### When is the best time to go to Middletown? > The most popular time to visit Middletown is during the summer months, particularly July. At this time, the town is vibrant with events and outdoor activities, with average temperatures around 25°C, creating a delightful atmosphere for exploration. Visitors can enjoy a variety of festivals, farmers' markets, and outdoor concerts that bring the community together and showcase the local culture. > > > > 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? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Middletown hotel for you. ### How can I save on a Middletown hotel booking with Expedia? > Members always get our best prices. Find our best Middletown hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings. ### How much is the nightly rate at a Middletown hotel? > Prices for hotels in Middletown often vary, but you can find a great deal from CA $90 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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[Hotels near Winchester-Frederick County Convention & Visitors Bureau](https://www.expedia.ca/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Pet-Friendly-Hotel.0-0-d6056879-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Winchester Hotels](https://www.expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels) - [Hotels near Winchester Medical Center](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) - [Flights to Front Royal](https://www.expedia.ca/Cheap-Flights-To-Front-Royal.d7312.Travel-Guide-Flights) - [Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Star Tannery](https://www.expedia.ca/lp/flights/3000460674/flights-from-star-tannery) - [Flights from Blacksburg (BCB) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester) - [Flights from Hartford (BDL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester) - [Flights from Baltimore (BWI) to Front Royal (FRR)](https://www.expedia.ca/lp/flights/bwi/frr/baltimore-to-front-royal) - [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester) - [Flights from Fort Lauderdale (FLL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO)](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Melbourne (MEL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester) - [Flights from Sarasota (SRQ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester) - [Flights from Syracuse (SYR) to Winchester (WGO)](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester) - [Flights from Calgary (YYC) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester) - [Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) - [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Front Royal Entrance Shenandoah National Park](https://www.expedia.ca/Front-Royal-Entrance-Shenandoah-National-Park-Front-Royal.d6129961.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Skyline Caverns](https://www.expedia.ca/Skyline-Caverns-Front-Royal.d6093201.Vacation-Attraction) - [Budget Rental Cars in Front Royal](https://www.expedia.ca/Budget-Car-Rentals-In-Front-Royal.d7312-c39.Car-Rental-Guide-Suppliers) - [Car rental Front Royal](https://www.expedia.ca/Car-Rentals-In-Front-Royal.d7312.Car-Rental-Guide) - [Things to do in Winchester](https://www.expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities) - [Book Hotels in Middletown on Expedia.com](https://www.expedia.com/Middletown-Hotels.d12013.Travel-Guide-Hotels) ![](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 ![QR code to download the app](data:image/png;base64,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)