A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check availability on Winchester Romantic Hotels

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Winchester romantic hotels

A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.
A hotel dining area with multiple tables and chairs, large windows, and a television screen.
Lobby
A hotel room with two beds, a desk with a TV, a lamp, and a view of the outdoors.

1. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester
United States
John
₩133,289
₩148,350 total
includes taxes & fees
Oct 18 - Oct 19
Comfort Inn & Suites Winchester
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
A spacious living room with a fireplace, leather sofa, armchairs, and a large painting.
A bar area with a piano, seating, and a bar counter with bottles.
A spacious lobby with a round table, chairs, a chandelier, and an American flag.

2. The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester
United States
Carol
₩174,743
₩197,983 total
includes taxes & fees
Oct 28 - Oct 29
The George Washington Hotel, A Wyndham Grand Hotel
A rustic interior with wooden tables and chairs, a brick floor, and a wooden ceiling.
A large brick building with a central entrance, multiple windows, and a covered walkway.
Bar (on property)
A room with wooden flooring, two leather chairs, a wooden table with a green felt top, a brass lamp, and a large mirror on the wall.

3. Wayside Inn

Wayside Inn
Middletown
United States
Luanne
₩91,138
₩113,914 total
includes taxes & fees
Oct 19 - Oct 20
Wayside Inn
A covered porch with white columns, a bench, and hanging flower baskets.
A dining area with tables set for service, large windows with views of greenery, and a chandelier.
A covered porch with wooden benches and potted plants, a tiled floor, and a view of a grassy yard.
A bar area with wooden shelves stocked with bottles, a bar counter, and leather bar stools.

4. L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
Boyce
United States
Henry
₩385,995
₩425,753 total
includes taxes & fees
Nov 2 - Nov 3
L'Auberge Provencale Inn & Restaurant
A metal archway in a park with a rainbow in the background.
A hotel room with a large bed, two armchairs, a small table with a lamp, a round mirror, and a window with curtains.
A brick building with a sign reading "Boston - Bryant Theatre."
A wooden table with a wine bottle and two glasses on it, set outdoors with a view of greenery in the background.

5. ANS Inn & Suites

ANS Inn & Suites
Winchester
United States
Valerie
₩96,499
₩115,124 total
includes taxes & fees
Oct 12 - Oct 13
ANS Inn & Suites
A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.
A dining area with a table set for two, featuring a bowl of bread, a glass of wine, and a vase of flowers.
A cozy room with a fireplace, wooden paneling, and comfortable seating.
A bathroom with a large window, a bathtub, and a view of a green landscape.

6. Glen Gordon Manor

Glen Gordon Manor
Huntly
United States
Alexander and Judith
₩427,543
₩492,961 total
includes taxes & fees
Nov 4 - Nov 5
Glen Gordon Manor
A hotel room with a large bed, a bathroom with a bathtub, and a framed picture on the wall.
A multi-story hotel with a courtyard, outdoor seating, and a guest parking area.
A breakfast counter with various food items and a coffee machine.
A Baymont Inn & Suites reception desk with a blue wall, two overhead lights, and a Dell computer.

7. Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
Front Royal
Netherlands
pieter
₩78,606
₩87,488 total
includes taxes & fees
Nov 4 - Nov 5
Baymont by Wyndham Front Royal Near Shenandoah National Park
A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.
A dining room with a view of a green landscape, large windows, and a ceiling fan.
A room with a wooden floor, a small wooden table with a coffee maker, a chair, and a door leading to a balcony with a wooden railing.
A hotel room with a bed, a bedside table with a wine bottle and glass, and a fruit platter on the table.

8. Hillbrook Inn

Hillbrook Inn
Charles Town
United States
Cecile
₩199,699
₩257,170 total
includes taxes & fees
Oct 13 - Oct 14
Hillbrook Inn
A staircase with a stone wall, wooden steps, and a red carpet leading to a room with a wooden table and chairs.
A red brick building with a white door, a welcome sign, and outdoor seating with metal chairs and tables.
A red brick building with a black door, two wall-mounted lanterns, and a sign for Light Horse Inn.
A bedroom with a bed, curtains, a ceiling fan, a dresser, and a rustic wall.

9. Light Horse Inn

Light Horse Inn
Harpers Ferry
United States
Rich
₩199,029
₩212,961 total
includes taxes & fees
Nov 2 - Nov 3
Light Horse Inn
A two-story brick building with a balcony and columns, featuring multiple flags and outdoor seating.
A bar area with wooden furniture, a variety of bottles, and framed pictures on the walls.
A modern living room with a curved glass coffee table, a black leather sofa, and a large window offering a view of the outdoors.
An outdoor patio with stone flooring, metal and white wicker furniture, and flowering trees.

10. The Country Inn of Berkeley Springs

The Country Inn of Berkeley Springs
Berkeley Springs
United States
Diyana
₩174,220
₩196,870 total
includes taxes & fees
Oct 12 - Oct 13
The Country Inn of Berkeley Springs
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Top Winchester Hotel Reviews

Skyland

Skyland

10/10 Excellent
"We enjoyed our stay- the property is right on Skyline Drive- so convenient! The room was clean and very basic- nothing fancy or upscale about this property- something you would expect from a lodge within the Shenandoah National Park"
Geoffrey 1-night trip
Posted 5 hours ago
Skyland
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"This facility is excellent. The breakfast was excellent with many extras including honey packets. It has a very good selection 8 plus to add to yogurt, etc. I had a very nice cream cheese bagel with honey drizzled. They also had eggs and sausage. It also has a coffee/herbal tea station in the lobby. The pool was spotless. Perfectly clean. Perfect. The room was spacious. There were plenty of spaces to congregate both inside and outside. The seasonal fall decor was a very nice touch. It was very full and impressive. I very highly reccomend this facility. Superb."
Deborah 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Winchester, VA
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"Great place to stay in Luray."
Eric 1-night trip
Posted 2 days ago
Mimslyn Inn Historic Hotels Of America

Frequently asked questions

Searching for romantic hotels in Winchester?
If you and your partner need a romantic escape, we'd like to help you plan for it. Couples choose Winchester for its scenic landscape and top-notch restaurants. If you're hoping to explore some cultural attractions while you're in town, Bright Box Theater or Winchester Little Theater make for a fun date night. Whether you'd like to get a couple's massage or watch the sunset from your balcony, there are 3 hotels and other accommodations in Winchester.
When is the best time of year for a romantic getaway to Winchester?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Winchester: The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What is there to do in Winchester?
There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Winchester. If you're hoping to see some of the area's cultural attractions, you and your partner will love Winchester for its interesting historical sites and major shopping area. You might think about stopping by Bright Box Theater, Shenandoah Valley Discovery Museum, or Patsy Cline Historic House while you're seeing the sights.
What's the best way to get to Winchester and around town during my romantic getaway?
This information about transportation options in Winchester might help your romantic trip get off to a smooth start: If you're looking to fly to Winchester, the closest major airport is Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

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