Title: Book the Best ROMANTIC Hotels in Middletown, VA from CA $123 - Middletown Romantic Getaways | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d12013.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d12013.Travel-Guide-VacationRentals)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d12013.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d12013.Destination-Travel-Guides) ![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 Romantic Hotels in Middletown, VA from CA $123 - ![](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 ## Check availability on Middletown Romantic Hotels Tonight [Dec 22 - Dec 23](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-12-22&endDate=2025-12-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-12-23&endDate=2025-12-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next 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&travelerType=romantic) ## Our top choices for Middletown romantic hotels ![Dining](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/a3d72fc4.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) ![Point of interest](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/9e80fe83.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 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) Middletown 9.2/10 Wonderful (417) "Historic inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $99 CA $123 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.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) ![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) ![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) ### Holiday Inn Express Woodstock-Shenandoah Valley by IHG [](https://www.expedia.ca/Luray-Hotels-Holiday-Inn-Express-Woodstock-Shenandoah-Valley.h20598.Hotel-Information) Woodstock 9.0/10 Wonderful (1000) "Excellent hotel. Rooms were clean, food was good. Staff was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy CA $123 CA $138 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Luray-Hotels-Holiday-Inn-Express-Woodstock-Shenandoah-Valley.h20598.Hotel-Information) ![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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/50dde1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Old Town Winchester 9.4/10 Exceptional (1009) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHARLES CA $175 CA $198 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/636f5ae3.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) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/8a97ffc7.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 (787) "Great staff, very clean room with a good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim CA $140 CA $152 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/2fa2dbbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar)](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/5daa33ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/ca692cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/0ec10473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) Winchester 9.2/10 Wonderful (849) "Super friendly reception and perfectly clean room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dwight CA $146 CA $165 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9874bc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/4c7ae30b.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 (1006) "Friendly staff, nice clean room, hotel restaurant was delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy CA $135 CA $149 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a7fe3c2c.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) ![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) ### Hilton Garden Inn Winchester [](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.Hotel-Information) Winchester 8.8/10 Excellent (510) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DONNA D CA $139 CA $158 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/22bccc43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/23fa04d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/8c81eb2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/93104572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Auberge Provencale Inn & Restaurant [](https://www.expedia.ca/Winchester-Hotels-LAuberge-Provencale.h15945622.Hotel-Information) Boyce 9.6/10 Exceptional (174) "This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DONNA CA $291 CA $322 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Winchester-Hotels-LAuberge-Provencale.h15945622.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/6e95af26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Windsor Suite) | Deep soaking bathtub](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/c20a2340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/480b5c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/df92df6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glen Gordon Manor [](https://www.expedia.ca/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information) Huntly 9.8/10 Exceptional (95) "Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KYLE CA $371 CA $406 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/71000000/70970000/70967300/70967291/ec5927b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70970000/70967300/70967291/9e34e2bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70970000/70967300/70967291/ebc1c9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70970000/70967300/70967291/0d1e0d13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Glamper w/ Hot Tub and full bathroom-sleep 6 [](https://www.expedia.ca/Large-Glamper-W-Hot-Tub-And-Full-Bathroom-Sleep-6.h70967291.Hotel-Information) Capon Bridge 9.8/10 Exceptional (24) "We absolutely loved this place! The glamper had everything we needed and more! The hot tub was super relaxing and the host is super responsive! Would definitely stay here again in the future." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $157 CA $336 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Large-Glamper-W-Hot-Tub-And-Full-Bathroom-Sleep-6.h70967291.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=2026-01-05&endDate=2026-01-06®ionId=12013&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Middletown Hotel Reviews ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Great staff" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![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 10/10 Excellent "Yes" [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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 10/10 Excellent "Rooms were clean. Pleasant and professional staff. Good breakfast." [](https://expedia.ca/Luray-Hotels-Holiday-Inn-Express-Woodstock-Shenandoah-Valley.h20598.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "Nice, clean, quiet rooms. Staff were polite and professional. I would stay here again. " [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Middletown? ### When is the best time of year for a romantic getaway to Middletown? ### What is there to do in Middletown? ### What's the best way to get to Middletown and around town during my romantic getaway? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - 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) - [B&B in College Park ](https://www.expedia.ca/College-Park-Bed-And-Breakfast.d553248635975870482-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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