Find Romantic Hotels in Old Town 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 Old Town Winchester Romantic Hotels

Top Old Town Winchester Romantic Hotels

The George Washington Hotel, A Wyndham Grand Hotel
2 restaurants, breakfast, lunch, dinner served; American cuisine
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.4 out of 10, Exceptional, (1015)
"Very nice hotel "
The price is NT$3,873
NT$4,388 total
includes taxes & fees
Oct 26 - Oct 27
The George Washington Hotel, A Wyndham Grand Hotel
Hampton Inn Front Royal
Lobby
Hampton Inn Front Royal
2.5 star property
9.0 out of 10, Wonderful, (1010)
"convenient to Shenandoah Park"
The price is NT$3,235
NT$3,601 total
includes taxes & fees
Nov 9 - Nov 10
Hampton Inn Front Royal
SpringHill Suites by Marriott Winchester
1 bedroom, pillowtop beds, desk, laptop workspace
SpringHill Suites by Marriott Winchester
2.5 star property
9.4 out of 10, Exceptional, (738)
"Great location clean facilities "
The price is NT$3,413
NT$3,713 total
includes taxes & fees
Nov 2 - Nov 3
SpringHill Suites by Marriott Winchester
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
9.0 out of 10, Wonderful, (1005)
"The hotel was clean which is the priority for me. The rooms were big, beds comfortable and amenities (hot tub) a added perk "
The price is NT$3,486
NT$3,937 total
includes taxes & fees
Nov 9 - Nov 10
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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, (817)
"Friendly and efficient staff, well-maintained breakfast area with good selections"
The price is NT$3,235
NT$3,665 total
includes taxes & fees
Oct 26 - Oct 27
Hampton Inn Winchester N/Conference Center, VA
Hillbrook Inn
Property amenity
Hillbrook Inn
4.0 star property
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!"
The price is NT$5,474
NT$6,896 total
includes taxes & fees
Oct 26 - Oct 27
Hillbrook Inn
The Inn at Charles Town - Hollywood Casino
Restaurant
The Inn at Charles Town - Hollywood Casino
3.0 star property
8.6 out of 10, Excellent, (499)
"It is convenient to the casino and racetrack. The continental breakfast was average at best. For a tremendous breakfast try the Charlestown Family Diner across the street from this property."
The price is NT$3,683
NT$4,432 total
includes taxes & fees
Nov 3 - Nov 4
The Inn at Charles Town - Hollywood Casino
Hilton Garden Inn Winchester
Indoor pool
Hilton Garden Inn Winchester
3.0 star property
8.8 out of 10, Excellent, (496)
"Great hotel"
The price is NT$2,920
NT$3,308 total
includes taxes & fees
Nov 9 - Nov 10
Hilton Garden Inn Winchester
L'Auberge Provencale Inn & Restaurant
Terrace/patio
L'Auberge Provencale Inn & Restaurant
4.0 star property
9.6 out of 10, Exceptional, (172)
"Wonderful staff and service!"
The price is NT$9,144
NT$10,086 total
includes taxes & fees
Oct 15 - Oct 16
L'Auberge Provencale Inn & Restaurant
Wayside Inn
Bar (on property)
Wayside Inn
3.5 star property
9.2 out of 10, Wonderful, (407)
"Clean room and friendly staff. Air conditioning was very noisy and the inn needs some upkeep, but we would stay there again."
The price is NT$3,482
NT$4,146 total
includes taxes & fees
Oct 27 - Oct 28
Wayside Inn
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Was just one night with group of friends. Location was great, easy check in and out, good breakfast and comfy beds. Would highly recommend. "
Kim 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Winchester

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Old Town Winchester?
Are you looking for a romantic vacation? 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'd like to stay close to a particular destination, you can sort properties by neighborhood 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 experiencing 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 a stop at Bright Box Theater, Shenandoah Valley Discovery Museum, or Old Court House Civil War Museum.