Find Romantic Hotels in Winchester, VA

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Check availability on Winchester Romantic Hotels

Our top choices for Winchester romantic hotels

Indoor pool
Hampton Inn Front Royal

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,006 reviews)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is ₩141,837
₩157,864 total
includes taxes & fees
Jan 18 - Jan 19
Hampton Inn Front Royal
Exterior
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (796 reviews)
"Great stay!"
United States
Rene
The price is ₩156,271
₩170,022 total
includes taxes & fees
Jan 18 - Jan 19
SpringHill Suites by Marriott Winchester
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean rooms and property. Staff was amazing. Hot tub and pool area were great and clean. Very comfortable stay. Only issue was shower was very slow to drain but confident staff will fix it for next"
United States
Edward
The price is ₩141,837
₩156,446 total
includes taxes & fees
Jan 18 - Jan 19
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,005 reviews)
"Great hotel!"
United States
CHARLES
The price is ₩184,092
₩208,575 total
includes taxes & fees
Jan 19 - Jan 20
The George Washington Hotel, A Wyndham Grand Hotel
Dining
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (419 reviews)
"Historic inn. "
United States
Anonymous traveler
The price is ₩104,656
₩129,956 total
includes taxes & fees
Jan 11 - Jan 12
Wayside Inn
Interior
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
Winchester
8.8 out of 10, Excellent, (514 reviews)
"Great hotel"
United States
DONNA D
The price is ₩146,620
₩166,119 total
includes taxes & fees
Jan 19 - Jan 20
Hilton Garden Inn Winchester
Garden
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (175 reviews)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is ₩332,863
₩367,147 total
includes taxes & fees
Jan 11 - Jan 12
L'Auberge Provencale Inn & Restaurant
Exterior
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (96 reviews)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is ₩392,501
₩429,008 total
includes taxes & fees
Feb 8 - Feb 9
Glen Gordon Manor
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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Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Clean room; really comfortable bed. Great staff "
william 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"I enjoyed everything about my visit "
Monica 1-night trip
Posted 9 days ago
Lansdowne Resort and Spa

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 4 hotels and other accommodations in Winchester.
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.