Romantic Hotels in Winchester, Virginia

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Top Winchester Romantic Hotels

Celebration Retreat
Front of property

Celebration Retreat

5.0 star property
Celebration Retreat
Smithfield Farm B&B
Miscellaneous

Smithfield Farm B&B

3.0 star property
9.4 out of 10, Exceptional, (92)
"One of the most beautiful homes and areas I’ve ever been too. Everything was beautiful and breakfast was delicious. If I have a chance to go again I will."
Smithfield Farm B&B
The George Washington Hotel, A Wyndham Grand Hotel
Bar (on property)

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.2 out of 10, Wonderful, (1006)
"It’s very close to the local walking mall with stores and nice restaurants. parking was not a problem."
The price is P7,463
P8,456 total
includes taxes & fees
Dec 1 - Dec 2
The George Washington Hotel, A Wyndham Grand Hotel
Wayside Inn
Serves dinner and happy hour

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (372)
"Love the inside. Rooms and public spaces were fantastic. Outside needs some rehab. "
The price is P6,194
P7,422 total
includes taxes & fees
Nov 24 - Nov 25
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
Exterior

La Quinta Inn & Suites by Wyndham Winchester

2.5 star property
9.2 out of 10, Wonderful, (1725)
"Clean, good staff, close to everything "
The price is P5,610
P6,103 total
includes taxes & fees
Dec 1 - Dec 2
La Quinta Inn & Suites by Wyndham Winchester
Country Inn & Suites by Radisson, Winchester, VA
Desk, laptop workspace, blackout drapes, iron/ironing board

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.6 out of 10, Excellent, (1003)
"I been to this hotel many time and was my first deception. My room was closed to the hyway and it was very noisy. "
The price is P4,118
P4,480 total
includes taxes & fees
Dec 22 - Dec 23
Country Inn & Suites by Radisson, Winchester, VA
Hampton Inn Winchester N/Conference Center, VA
Snack bar

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
9.2 out of 10, Wonderful, (716)
"Would like it closer to restaurants"
The price is P6,318
P7,159 total
includes taxes & fees
Dec 1 - Dec 2
Hampton Inn Winchester N/Conference Center, VA
Hampton Inn Winchester-University/Mall Area
Porch

Hampton Inn Winchester-University/Mall Area

2.5 star property
9.0 out of 10, Wonderful, (1015)
"The water was hot, it was clean, it was close to the highway, the bed was comfortable, the breakfast was great and finally the staff were professional friendly and helpful. What more can you ask for? The hotel is older but well looked after and clean. "
The price is P5,717
P6,477 total
includes taxes & fees
Dec 1 - Dec 2
Hampton Inn Winchester-University/Mall Area
DoubleTree by Hilton Front Royal Blue Ridge Shadows
In-room safe, individually decorated, individually furnished, desk

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
9.0 out of 10, Wonderful, (1047)
"Very convenient location for our trip. Exceptional property."
The price is P6,461
P7,303 total
includes taxes & fees
Dec 23 - Dec 24
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.
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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 want to spend some time strolling through captivating scenery with your love, you might make a visit to Jim Barnett Park, Frederick Douglass Park, or Friendship Park. 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 Shenandoah Valley Discovery Museum, Patsy Cline Historic House, or Museum of the Shenandoah Valley 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.