Find Romantic Hotels in Winchester, VA from CA $93

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Check availability on Winchester Romantic Hotels

Top Winchester Romantic Hotels

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, (792)
"A good solid Hampton inn, close to historic downtown with lots of restaurants and bars."
The price is CA $151
CA $171 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn Winchester N/Conference Center, VA
Hilton Garden Inn Winchester
Indoor pool

Hilton Garden Inn Winchester

3.0 star property
9.0 out of 10, Wonderful, (487)
"I have stayed here a few times and always enjoyed the stays."
The price is CA $151
CA $171 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Winchester
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (89)
"The location is good."
The price is CA $343
CA $375 total
includes taxes & fees
Aug 19 - Aug 20
Glen Gordon Manor
The Legacy Inn
40-inch flat-screen TV with digital channels, Netflix, Hulu

The Legacy Inn

3.0 star property
8.4 out of 10, Very good, (46)
"This was a unique property. It was clean and well maintained. There is no staff onsite but it was easy to get in and safe. "
The price is CA $93
CA $246 total
includes taxes & fees
Aug 25 - Aug 26
The Legacy Inn
Hillbrook Inn
Property amenity

Hillbrook Inn

4.0 star property
8.6 out of 10, Excellent, (668)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
The price is CA $263
CA $330 total
includes taxes & fees
Aug 28 - Aug 29
Hillbrook Inn
Clarion Hotel & Conference Center Leesburg
Free daily buffet breakfast

Clarion Hotel & Conference Center Leesburg

2.5 star property
6.6 out of 10, (1003)
"Property was very nice. "
The price is CA $139
CA $160 total
includes taxes & fees
Aug 31 - Sep 1
Clarion Hotel & Conference Center Leesburg
Inn at Evergreen
Free daily full breakfast

Inn at Evergreen

3.5 star property
9.4 out of 10, Exceptional, (127)
"Wonderful place to stay"
The price is CA $262
CA $299 total
includes taxes & fees
Aug 14 - Aug 15
Inn at Evergreen
The Inn at Grass Roots Hill
Property entrance

The Inn at Grass Roots Hill

3.0 star property
The price is CA $632
CA $720 total
includes taxes & fees
Aug 26 - Aug 27
The Inn at Grass Roots Hill
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

❤️ Secluded 1940s Romantic Tiny House on the River

9.8 out of 10, Exceptional, (59)
"We truly loved this location and definitely will be back!"
The price is CA $102
CA $197 total
includes taxes & fees
Sep 8 - Sep 9
❤️ Secluded 1940s Romantic Tiny House on the River
Hotel Laurance
TV

Hotel Laurance

3.5 star property
9.0 out of 10, Wonderful, (154)
"It was quaint."
The price is CA $338
CA $425 total
includes taxes & fees
Aug 14 - Aug 15
Hotel Laurance
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.

Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Bed comfy, dinner delicious. Lovely ambiance in lobby and enjoyed pool. "
Laurie 1-night trip
Posted 2 days ago
The George Washington Hotel, A Wyndham Grand Hotel

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 Winchester Little Theater 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.