Find Romantic Hotels in Winchester, VA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Romantic Hotels

Top Winchester Romantic Hotels

1 bedroom, pillowtop beds, desk, laptop workspace
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (764)
"Clean room, nice area, friendly staff "
United States
chad
The price is AED 393
AED 428 total
includes taxes & fees
7 Dec - 8 Dec
SpringHill Suites by Marriott Winchester
Lobby
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1002)
"We thoroughly enjoyed all aspects of our stay, and look forward to the next time."
United States
Dennis
The price is AED 350
AED 389 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn Front Royal
Bar (on property)
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, (1003)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is AED 436
AED 492 total
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Front Royal Blue Ridge Shadows
2 restaurants, breakfast, lunch, dinner served; American cuisine
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, (1013)
"Love this hotel and the location. Staff is super friendly. "
United States
Casey
The price is AED 465
AED 527 total
includes taxes & fees
23 Nov - 24 Nov
The George Washington Hotel, A Wyndham Grand Hotel
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

3.0 star property
Winchester
8.8 out of 10, Excellent, (505)
"Great hotel"
United States
DONNA D
The price is AED 351
AED 397 total
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Winchester
Terrace/patio
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

4.0 star property
Boyce
9.6 out of 10, Exceptional, (173)
"Wonderful staff and service!"
United States
Eliel Constantine
The price is AED 1,087
AED 1,199 total
includes taxes & fees
23 Nov - 24 Nov
L'Auberge Provencale Inn & Restaurant
Bar (on property)
Wayside Inn

Wayside Inn

3.5 star property
Middletown
9.2 out of 10, Wonderful, (414)
"Historic inn. "
United States
David
The price is AED 401
AED 479 total
includes taxes & fees
24 Nov - 25 Nov
Wayside Inn
Exterior
Glen Gordon Manor

Glen Gordon Manor

3.5 star property
Huntly
9.8 out of 10, Exceptional, (92)
"The location is good."
United States
Danny
The price is AED 915
AED 1,000 total
includes taxes & fees
19 Nov - 20 Nov
Glen Gordon Manor
Cookware/dishes/utensils
The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond

Linden
10.0 out of 10, Exceptional, (33)
"It was the perfect home away from home in a place that allowed our little family to take a breath of nature and just be. Close enough to many fun adventures. The amenities provided on the property also kept us very busy!"
United States
Brena H.
The price is AED 878
AED 1,916 total
includes taxes & fees
18 Nov - 19 Nov
The Pond Cabin: Hot Tub & Stocked Pond
Snack bar
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
Winchester
9.2 out of 10, Wonderful, (836)
"The hotel was clean, and the staff was friendly. "
United States
Brett
The price is AED 379
AED 429 total
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn Winchester N/Conference Center, VA
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.
View all properties

Top Winchester Hotel Reviews

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

10/10 Excellent
"All good. Quiet. Safe area. Good breakdaat. Easy check in. Good service. Loved it. Our fav Winchester hotel."
Kash 1-night trip
Posted 22 hours ago
Hampton Inn Winchester-University/Mall Area

Explore a world of travel with Expedia

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.
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. Other good choices for a romantic stay include Secret Gardens Carriage House and ANS Inn has clean, spacious rooms located on 5 acres with little traffic..
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.