Find Luxury Hotels in Winchester, VA

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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, (1002)
"Very good and convenient budget motel in Winchester, happy to recommend."
United States
Jane
The price is NT$2,121
NT$2,403 total
includes taxes & fees
Dec 21 - Dec 22
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 NT$2,121
NT$2,308 total
includes taxes & fees
Jan 12 - 2026/1/13
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 NT$2,246
NT$2,789 total
includes taxes & fees
Dec 15 - Dec 16
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 NT$1,934
NT$2,153 total
includes taxes & fees
Dec 16 - Dec 17
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, (1006)
"Great hotel!"
United States
CHARLES
The price is NT$3,951
NT$4,476 total
includes taxes & fees
Dec 21 - Dec 22
The George Washington Hotel, A Wyndham Grand Hotel
Desk, blackout drapes, free cribs/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, (1002)
"Really friendly staff, room was clean and perfect for our family and dog. "
United States
Sabrina
The price is NT$1,891
NT$2,058 total
includes taxes & fees
Jan 1 - 2026/1/2
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 NT$3,095
NT$3,506 total
includes taxes & fees
Jan 11 - 2026/1/12
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 traveler
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, (1002)
"great stay with breakfast too"
United States
James
The price is NT$2,134
NT$2,322 total
includes taxes & fees
Jan 4 - 2026/1/5
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.
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Top Winchester Hotel Reviews

Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

10/10 Excellent
"Good house keeping"
James 3-night trip
Posted 18 hours ago
Hilton Garden Inn Dulles North

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Frequently asked questions

Are you looking for a luxury hotel for your Winchester vacation?
Expedia can help you arrange a flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington Dulles Intl. 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 want 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 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'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 Patsy Cline Historic House. If you have extra time while you're in the area, you might want to see Museum of the Shenandoah Valley and Apple Blossom Mall.