Find Romantic Hotels in Winchester, VA

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Check availability on Winchester Romantic Hotels

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

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, (1011)
"Lovely! Welcomed at check in. Room is cozy and clean. Parking was easy. Great hotel for a stopover! "
The price is AED 465
AED 527 total
includes taxes & fees
16 Mar - 17 Mar
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, (386)
"Was a very fun atmosphere with and employees and also other guess very nice and friendly and excellent wings"
The price is AED 359
AED 432 total
includes taxes & fees
10 Apr - 11 Apr
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, (1862)
"Great clean hotel just off the interstate. "
The price is AED 363
AED 395 total
includes taxes & fees
2 Apr - 3 Apr
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, (1008)
"The hotel is well located in a shopping area with restaurants. Right off the highway. Staff was friendly. Very nice complementary breakfast. Would definitely stay there again."
The price is AED 325
AED 353 total
includes taxes & fees
14 Mar - 15 Mar
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, (735)
"Room upgrade from a year ago was awesome. Shower facilities were very good"
The price is AED 387
AED 439 total
includes taxes & fees
17 Mar - 18 Mar
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, (1003)
"Great breakfast"
The price is AED 371
AED 421 total
includes taxes & fees
16 Mar - 17 Mar
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, (1006)
"Very clean and comfortable!"
The price is AED 319
AED 363 total
includes taxes & fees
16 Mar - 17 Mar
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’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?
Secret Gardens Carriage House is a favorite guesthouse for couples, and features in-room fireplaces and a garden. Another good option for a romantic stay is Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed.
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.