Old Town Winchester Romantic Hotel

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Check availability on Old Town Winchester Romantic Hotel

Tonight
1 Dec - 2 Dec
Tomorrow
2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Old Town Winchester Romantic Hotel

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, (1010)
"Love this hotel and the location. Staff is super friendly. "
United States
Casey
The price is HK$986
HK$1,117 total
includes taxes & fees
2 Dec - 3 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Lobby
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1014)
"We thoroughly enjoyed all aspects of our stay, and look forward to the next time."
United States
Dennis
The price is HK$772
HK$860 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Front Royal
Pillow-top beds, desk, laptop workspace, blackout curtains
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (772)
"Clean room, nice area, friendly staff "
United States
chad
The price is HK$787
HK$857 total
includes taxes & fees
7 Dec - 8 Dec
SpringHill Suites by Marriott Winchester
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, (1007)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is HK$938
HK$1,058 total
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Restaurant
The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

3.0 star property
Charles Town
8.6 out of 10, Excellent, (516)
"Staff was courteous….helpful…room was clean and comfortable "
United States
David
The price is HK$934
HK$1,124 total
includes taxes & fees
30 Dec - 31 Dec
The Inn at Charles Town - Hollywood Casino
Property amenity
Hillbrook Inn

Hillbrook Inn

4.0 star property
Charles Town
8.6 out of 10, Excellent, (670)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is HK$1,324
HK$1,678 total
includes taxes & fees
3 Dec - 4 Dec
Hillbrook Inn
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

3.0 star property
Winchester
9.0 out of 10, Wonderful, (507)
"Great hotel"
United States
DONNA D
The price is HK$743
HK$842 total
includes taxes & fees
14 Dec - 15 Dec
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 HK$2,142
HK$2,363 total
includes taxes & fees
3 Dec - 4 Dec
L'Auberge Provencale Inn & Restaurant
Bar (on property)
Wayside Inn

Wayside Inn

3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
The price is HK$736
HK$889 total
includes taxes & fees
1 Jan - 2 Jan 2026
Wayside Inn
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, (843)
"The hotel was clean, and the staff was friendly. "
United States
Brett
The price is HK$803
HK$910 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 Old Town Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Clean and great historic building. It's rare to find a historic hotel like this that has such updated rooms. Convenient to all downtown has to offer. Really friendly staff, nicely heated pool. Great have Uno's on site which my kid loves."
CYNTHIA 1-night trip
Posted 1 day ago
The George Washington Hotel, A Wyndham Grand Hotel

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Frequently asked questions

Searching for romantic hotels in Old Town Winchester?
Are you in need of a romantic escape? Our guests also love Old Town Winchester for its array of dining options and interesting historical sites. If you'd like to explore some of the area's notable sights, you might make a stop by Bright Box Theater, Shenandoah Valley Discovery Museum or Old Court House Civil War Museum. If you're interested in staying near a particular destination, you can sort properties by neighbourhood or distance to top landmarks, so you'll be able to see everything on your list.
What is there to do in Old Town Winchester?
There's nothing better than seeing a new place with your sweetheart, so consider checking out all that Old Town Winchester has to offer. Couples looking for a little of everything will enjoy Old Town Winchester for its restaurants, bars and shopping. If you want to spend a day exploring, you might consider stopping at Bright Box Theater, Shenandoah Valley Discovery Museum or Old Court House Civil War Museum.