Find Romantic Hotels in Winchester, VA

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Pick from 14 Winchester Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Celebration Retreat
Billiards
Celebration Retreat
5.0 star property
Celebration Retreat
Smithfield Farm B&B
Exterior
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."
The price is AED 918
AED 1,013 total
includes taxes & fees
11 Nov - 12 Nov
Smithfield Farm B&B
The George Washington Hotel, A Wyndham Grand Hotel
Exterior
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.2 out of 10, Wonderful, (1004)
"Great property "
The price is AED 465
AED 527 total
includes taxes & fees
11 Nov - 12 Nov
The George Washington Hotel, A Wyndham Grand Hotel
Wayside Inn
Exterior
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 AED 343
AED 415 total
includes taxes & fees
10 Nov - 11 Nov
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
9.0 out of 10, Wonderful, (1673)
"Satisfied"
The price is AED 350
AED 380 total
includes taxes & fees
1 Dec - 2 Dec
La Quinta Inn & Suites by Wyndham Winchester
Country Inn & Suites by Radisson, Winchester, VA
Lobby
Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
8.6 out of 10, Excellent, (1001)
"Friendly staff clean good value for money. Would stay there again"
The price is AED 308
AED 335 total
includes taxes & fees
24 Nov - 25 Nov
Country Inn & Suites by Radisson, Winchester, VA
Hampton Inn Winchester N/Conference Center, VA
Exterior
Hampton Inn Winchester N/Conference Center, VA
2.5 star property
9.2 out of 10, Wonderful, (712)
"I was charged an extra dollar on my bank statement compared to the receipt. A dollar is not a lot but if they do this to everyone it can add up. Bad business practice"
The price is AED 393
AED 446 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn Winchester N/Conference Center, VA
Hampton Inn Winchester-University/Mall Area
Pool
Hampton Inn Winchester-University/Mall Area
2.5 star property
9.0 out of 10, Wonderful, (1000)
"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 AED 297
AED 336 total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn Winchester-University/Mall Area
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Lobby
DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
9.0 out of 10, Wonderful, (1003)
"Excellent room. Air conditioner is a bit loud, but otherwise very clean and modern."
The price is AED 403
AED 455 total
includes taxes & fees
17 Nov - 18 Nov
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.
What's the best hotel for a couple visiting Winchester?
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed is a favorite guesthouse for couples, and features a garden and laundry facilities.
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 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.