Search Luxury Hotels in Winchester

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 Luxury Hotels

Our top choices for Winchester luxury hotels

Coffee service
Motel 6 Winchester, VA

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.2 out of 10, Very good, (1003)
"Very good and convenient budget motel in Winchester, happy to recommend."
United States
Jane
The price is 1.792.352 ₫
2.030.664 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Motel 6 Winchester, VA
Lobby
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1081)
"Good price, good location "
United States
George
The price is 1.792.616 ₫
1.950.261 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Travelodge by Wyndham Winchester
Bar (on property)
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
The price is 1.898.064 ₫
2.356.922 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Wayside Inn
Building design
Hotel Strasburg

Hotel Strasburg

Hotel Strasburg
3.0 star property
Strasburg
7.8 out of 10, Good, (731)
"The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!"
United States
Merry
Hotel Strasburg
Exterior
Twi-Lite Inn

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very good, (540)
"Great pool and quiet area to stay in"
United States
Matthew
The price is 1.634.444 ₫
1.819.242 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Twi-Lite Inn
2 restaurants, breakfast, lunch, dinner served; American cuisine
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, (1007)
"Great hotel!"
United States
CHARLES
The price is 3.338.747 ₫
3.782.801 ₫ total
includes taxes & fees
17 Dec - 18 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Desk, blackout curtains, free cots/infant beds, free WiFi
Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA
2.0 star property
Winchester
7.4 out of 10, Good, (1001)
"Really friendly staff, room was clean and perfect for our family and dog. "
United States
Sabrina
The price is 1.594.637 ₫
1.734.964 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Red Roof Inn Winchester, VA
Porch
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1000)
"Staff, clean room, very comfortable bed!"
United States
Terri
The price is 2.615.904 ₫
2.963.820 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Winchester-University/Mall Area
Restaurant
Clarion Inn & Conference Center

Clarion Inn & Conference Center

Clarion Inn & Conference Center
2.5 star property
Winchester
7.8 out of 10, Good, (952)
"Great location and staff... spacious and clean will definitely be back "
United States
Anonymous traveller
Clarion Inn & Conference Center
Lobby
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1000)
"The rooms were clean and the facility seemed safe and well maintained. The room had seen many patches and repairs and had a distinct smell. The indoor pool, “gym” and breakfast were a plus. "
United States
tyshia
The price is 1.800.016 ₫
1.958.418 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleep Inn & Suites Winchester near University
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

Explore a world of travel with Expedia

Frequently asked questions

Are you looking for a luxury hotel for your Winchester holiday?
Expedia can help you arrange a flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington Dulles International Airport (IAD) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to get what you'd like to make your stay relaxing and comfortable. If you want an upscale hotel with fine dining, a spa or several swimming pools, Expedia can help you find the best luxury hotel experience that Winchester has to offer. During your visit, you might want to enjoy the great views and shopping which Winchester is known for.
When can I expect good weather in Winchester?
Planning for the weather is a good way to make your trip to Winchester relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What's there to see and do in Winchester?
Enjoy all that Winchester has to offer and visit Bright Box Theater, Shenandoah Valley Discovery Museum and Museum of the Shenandoah Valley. If you have extra time while you're in the area, you might want to see Apple Blossom Mall and Rock Harbor Golf Course.