Find Romantic Hotels in Winchester, VA

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Check availability on Winchester Romantic Hotels

Tonight
6 Jun - 7 Jun
Tomorrow
7 Jun - 8 Jun
This weekend
6 Jun - 8 Jun
Next weekend
13 Jun - 15 Jun

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
Bar (on property)

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1007)
"Perfect hotel in a great location!!!"
The price is SAR 475
SAR 538 total
includes taxes & fees
12 Jun - 13 Jun
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, (392)
"It was quaint and interesting, but beware if you don’t like the smell of antiques. I had to track down staff to check in and call the manager who frankly seemed a bit miffed that I called her. Staff member was friendly upon arrival. Water pressure in the shower was not great, although the room was clean."
The price is SAR 362
SAR 437 total
includes taxes & fees
8 Jun - 9 Jun
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

3.0 star property
9.2 out of 10, Wonderful, (2040)
"Excellent stay"
The price is SAR 389
SAR 423 total
includes taxes & fees
6 Jul - 7 Jul
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, (1004)
"Great stay for a great price!"
The price is SAR 347
SAR 378 total
includes taxes & fees
15 Jun - 16 Jun
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, (762)
"Very nice and new hotel great room and nice bathroom will stay there again when we come to visit my Son in Berryville"
The price is SAR 411
SAR 466 total
includes taxes & fees
15 Jun - 16 Jun
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, (1000)
"I loved everything about this hotel mainly the cleanliness and comfort. The front desk staff was very friendly."
The price is SAR 421
SAR 477 total
includes taxes & fees
15 Jun - 16 Jun
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, (1001)
"Stayed here for my spring trip to Shenandoah National Park, and had a perfect time. The hotel had everything I needed and the hot tub/pool were excellent. "
The price is SAR 443
SAR 500 total
includes taxes & fees
15 Jun - 16 Jun
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.

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.
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. Another good option for a romantic stay is Secret Gardens Carriage House.
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 Mt Hebron Cemetery 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.