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

Tonight
7 Feb - 8 Feb
Tomorrow
8 Feb - 9 Feb
This weekend
7 Feb - 9 Feb
Next weekend
14 Feb - 16 Feb

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, (1006)
"Beautiful old hotel with a rich history. Room was comfortable. The shower was challenging to figure out all the valves. "
The price is AED 465
AED 527 total
includes taxes & fees
13 Feb - 14 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)
"Was a very fun atmosphere with and employees and also other guess very nice and friendly and excellent wings"
The price is AED 275
AED 341 total
includes taxes & fees
8 Feb - 9 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 AED 384
AED 418 total
includes taxes & fees
9 Feb - 10 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)
"Staff was great and we loved our stay. Breakfast was good too. The only bad part was no hot water for tea or coffee downstairs."
The price is AED 309
AED 336 total
includes taxes & fees
9 Feb - 10 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)
"We only reserved a room here because it was half way to our destination and we needed an overnight stay. We were sorry we could only stay one night! I have to say I think this was the cleanest hotel I’ve ever stayed in! The lobby was immaculate and we watch a woman cleaning it during breakfast…it was obvious she CARED about her job which explained why it was so nice. Breakfast was awesome, well done, Finally, the staff was so friendly and helpful!!! Both the check in and check out staff...
The price is AED 390
AED 442 total
includes taxes & fees
14 Feb - 15 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, (1002)
"Great stay for access to university."
The price is AED 356
AED 403 total
includes taxes & fees
23 Feb - 24 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 AED 319
AED 363 total
includes taxes & fees
13 Feb - 14 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.