Winchester Hotel Guide - Romantic Hotels in Winchester, Virginia

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check availability on Winchester Romantic Hotels

Tonight
7 May - 8 May
Tomorrow
8 May - 9 May
This weekend
9 May - 11 May
Next weekend
16 May - 18 May

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, (1004)
"Loved our stay!"
The price is €119
includes taxes & fees
26 May - 27 May
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, (388)
"This inn is absolutely amazing. Staff went above and beyond to ensure we were comfortable and our stay was memorable. We plan to come back very soon! "
The price is €111
includes taxes & fees
8 May - 9 May
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, (1983)
"Great for a short visit"
The price is €90
includes taxes & fees
11 May - 12 May
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)
"Clean, comfortable, pool was nice, breakfast was good "
The price is €93
includes taxes & fees
11 May - 12 May
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, (751)
"Overall enjoyable stay. The room was clean and the amenities were very good. "
The price is €110
includes taxes & fees
18 May - 19 May
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)
"The property is attractive and the staff was excellent. "
The price is €111
includes taxes & fees
14 May - 15 May
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, (1002)
"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 €121
includes taxes & fees
11 May - 12 May
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 holiday, we’ve got just the thing. 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 sip a glass of champagne or lounge around in luxurious bedding, there are 3 hotels and other accommodations in Winchester.
What's the best accommodation for a couple going to Winchester?
Secret Gardens Carriage House is a favourite guest house for couples, and features a garden and laundry facilities. Another good option for your romantic getaway is Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed.
How many romantic hotels will we find 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, take a look at these details about year-round temperatures in Winchester: The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What is there to do in Winchester?
There’s nothing better than experiencing 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 Stonewall Jackson’s Headquarters 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 getaway go off without a hitch: If you’re looking to fly to Winchester, the closest major airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city centre. If you’d like to venture out around the area, you may want a rental car for your journey.