A white neoclassical building with columns, an American flag, and a clock tower.

Search Luxury Hotels in Old Town Winchester

  • 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 Luxury Hotels

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Old Town Winchester luxury hotels

A covered porch with white columns, a bench, and hanging flower baskets.

1. L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.4 out of 10, Exceptional, (180 reviews)
The price is ฿11,689
฿12,893 total
includes taxes & fees
30 Sept - 1 Oct
L'Auberge Provencale Inn & Restaurant
A restaurant interior with a bar area, seating, and artwork on the walls.

2. 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, (1,000 reviews)
The price is ฿3,561
฿3,927 total
includes taxes & fees
27 Oct - 28 Oct
DoubleTree by Hilton Front Royal Blue Ridge Shadows
A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.

3. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (691 reviews)
The price is ฿4,975
฿6,406 total
includes taxes & fees
6 Oct - 7 Oct
Hillbrook 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
"Hotel is great. It was hard to get in touch with the front desk. Expedia sit didn't provide the phone number. When I finally got the number from the Expedia information desk it went unanswered without any way to leave a message."
Yelena 1-night trip
Posted 19 hours ago
La Quinta Inn & Suites by Wyndham Winchester
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park

8/10 Good
"Good place to stay...close to Shenandoah NP."
Keith 3-night trip
Posted 3 days ago
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Old Town Winchester?
Let Expedia help you arrange your flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington Dulles International Airport (IAD) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Old Town Winchester has to offer. During your visit, you might want to enjoy the restaurants and bars which Old Town Winchester is known for.
What's there to see and do in Old Town Winchester?
Enjoy all that Old Town Winchester has to offer when you visit Bright Box Theater, Shenandoah Valley Discovery Museum and Old Court House Civil War Museum. If you have extra time while you're in the area, you might want to stop by Handley Regional Library and George Washington's Office.