Find Romantic Hotels in Winchester, VA

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Compare Winchester Romantic Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Celebration Retreat
Billiards

Celebration Retreat

5.0 star property
Celebration Retreat
The George Washington Hotel, A Wyndham Grand Hotel
Exterior

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1005)
"Wonderful time great hiotel"
The price is AED 465
AED 527 total
includes taxes & fees
7 Jan - 8 January 2025
The George Washington Hotel, A Wyndham Grand Hotel
Wayside Inn
Exterior

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (377)
"Love the inside. Rooms and public spaces were fantastic. Outside needs some rehab. "
The price is AED 275
AED 341 total
includes taxes & fees
1 Jan - 2 January 2025
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, (1768)
"Fantastic each time we go. "
The price is AED 391
AED 425 total
includes taxes & fees
5 Jan - 6 January 2025
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)
"Stay was pleasant. A nice pet friendly option "
The price is AED 328
AED 357 total
includes taxes & fees
5 Jan - 6 January 2025
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, (725)
"Staff at check in were very nice. Room was clean. Hotel is close to the interstate. Shopping and restaurants within 10 minutes. Immediate surrounding area is a bit run down, but the hotel inside is nicer than expected. We were located on the 1st floor, which was nice because we had a dog. Walmart was only about 10 mins away, and also lots of big shopping areas. "
The price is AED 393
AED 446 total
includes taxes & fees
7 Jan - 8 January 2025
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 front desk clerk was very helpful."
The price is AED 356
AED 403 total
includes taxes & fees
12 Jan - 13 January 2025
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, (1001)
"We had a great stay. Thank you"
The price is AED 319
AED 363 total
includes taxes & fees
7 Jan - 8 January 2025
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 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.