Find Romantic Hotels in Winchester, VA

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Check availability on Winchester Romantic Hotels

Tonight
Jul 24 - Jul 25
Tomorrow
Jul 25 - Jul 26
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Top Winchester Romantic Hotels

Celebration Retreat
Front of property

Celebration Retreat

5.0 star property
Celebration Retreat
The George Washington Hotel, A Wyndham Grand Hotel
Enjoy a romantic dinner under the stars at our outdoor dining area, where round tables are set with wine, candles, and appetizers.

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1007)
"Great location and clean hotel"
The price is ₩174,372
₩197,571 total
includes taxes & fees
Jul 27 - Jul 28
The George Washington Hotel, A Wyndham Grand Hotel
Wayside Inn
Enjoy a drink at the bar, surrounded by a selection of beverages and rustic charm.

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (401)
"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere. "
The price is ₩144,564
₩173,207 total
includes taxes & fees
Jul 27 - Jul 28
Wayside Inn
Hotel Strasburg
Building design

Hotel Strasburg

3.0 star property
7.8 out of 10, Good, (731)
"The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!"
Hotel Strasburg
La Quinta Inn & Suites by Wyndham Winchester
Experience the contemporary architecture of this hotel, featuring a striking entrance and a flat roof.

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
9.2 out of 10, Wonderful, (2088)
"Clean room, comfortable bed and friendly staff."
The price is ₩142,774
₩155,344 total
includes taxes & fees
Jul 27 - Jul 28
La Quinta Inn & Suites by Wyndham Winchester
Country Inn & Suites by Radisson, Winchester, VA
Cozy living room with a fireplace, wooden shelves, and a light-colored sofa.

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.8 out of 10, Excellent, (1009)
"Great stay for a great price!"
The price is ₩136,923
₩148,972 total
includes taxes & fees
Jul 27 - Jul 28
Country Inn & Suites by Radisson, Winchester, VA
Hampton Inn Winchester N/Conference Center, VA
Welcome to our reception area, featuring a central desk, a refrigerated display case, and a patterned rug.

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
9.2 out of 10, Wonderful, (783)
"Beautiful landscaping, very welcoming and kind staff, nice breakfast and sitting area, great option of room with full size refrigerator!"
The price is ₩162,669
₩184,305 total
includes taxes & fees
Jul 30 - Jul 31
Hampton Inn Winchester N/Conference Center, VA
Hampton Inn Winchester-University/Mall Area
Welcome to Hampton Inn, featuring a symmetrical design with a flat roof and large windows.

Hampton Inn Winchester-University/Mall Area

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Clean, friendly, comfortable bed and decent hot breakfast & fresh fruit. "
The price is ₩150,732
₩170,778 total
includes taxes & fees
Aug 3 - Aug 4
Hampton Inn Winchester-University/Mall Area
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Enjoy dining at this stylish restaurant with a central bar, high-top tables, and cozy booths.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
9.0 out of 10, Wonderful, (1006)
"Fantastic stay, thanks!"
The price is ₩162,669
₩183,553 total
includes taxes & fees
Aug 3 - Aug 4
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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.

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"The breakfast was nice, and though the property was smaller than I've seen elsewhere, it was very up-to-date and not a 70s or 80s style. Nice design overall. "
Denise 3-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

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.
How many romantic hotels are there in Winchester?
Expedia has 5 romantic Winchester hotels for you both to enjoy.
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 Winchester Little Theater 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.