Find Romantic Hotels in Winchester, VA

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check availability on Winchester Romantic Hotels

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
9.2 out of 10, Wonderful, (1005)
"The GW Hotel is excellent value and V friendly "
The price is SAR 443
SAR 502 total
includes taxes & fees
16 Feb - 17 Feb
The George Washington Hotel, A Wyndham Grand Hotel
Wayside Inn
Exterior

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (384)
"Very charming. I will stay there again."
The price is SAR 281
SAR 348 total
includes taxes & fees
9 Feb - 10 Feb
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, (1805)
"Very convenient for I 81 travellers. Our room was spacious and very comfortable. The fridge is very small. A larger one with a freezer section would be nice. We will stay again. "
The price is SAR 385
SAR 419 total
includes taxes & fees
12 Feb - 13 Feb
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)
"The room was clean and comfortable. Very spacious and quiet. Great place to stay."
The price is SAR 300
SAR 326 total
includes taxes & fees
16 Feb - 17 Feb
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, (731)
"The place was really nice! Check-in was easy and pleasant, the place was clean and breakfast was fantastic. It was already dark when we checked in, but it just seemed kind of an odd location, behind a convenience store, BUT the convenience store did have a Dunkin' Donuts!"
The price is SAR 399
SAR 451 total
includes taxes & fees
15 Feb - 16 Feb
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, (1001)
"Great stay for access to university."
The price is SAR 363
SAR 412 total
includes taxes & fees
16 Feb - 17 Feb
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, (1000)
" Quiet neighborhood, comfortable bed"
The price is SAR 326
SAR 371 total
includes taxes & fees
19 Feb - 20 Feb
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.
Don't see what you're looking for?
See all available properties in Winchester

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?
Find the secrets to peace and beauty here! is a favorite guesthouse for couples, and features a garden and a hot tub. 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.