Find Luxury Hotels in Winchester, VA

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Check availability on Winchester Luxury Hotels

Tonight
Sep 27 - Sep 28
Tomorrow
Sep 28 - Sep 29
Next weekend
Oct 3 - Oct 5
In two weeks
Oct 10 - Oct 12

Top Winchester Luxury Hotels

Motel 6 Winchester, VA
Coffee service

Motel 6 Winchester, VA

2.0 star property
8.2 out of 10, Very Good, (1008)
"Friendly staff, spotless rooms, safe property and location. Great place for those traveling with pets."
The price is ￥10,164
￥11,515 total
includes taxes & fees
Sep 28 - Sep 29
Motel 6 Winchester, VA
Travelodge by Wyndham Winchester
In-room safe, desk, iron/ironing board, free cribs/infant beds

Travelodge by Wyndham Winchester

2.5 star property
8.4 out of 10, Very Good, (1098)
"My favorite hotel in VA, always stay there when visiting friends and family. "
The price is ￥10,464
￥11,385 total
includes taxes & fees
Sep 29 - Sep 30
Travelodge by Wyndham Winchester
Wayside Inn
Bar (on property)

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (406)
"Rooms and property were beautiful. Wish they provided garbage cans and ash trays for outdoor seating. "
The price is ￥13,843
￥16,762 total
includes taxes & fees
Sep 28 - Sep 29
Wayside Inn
Hotel Strasburg
Building design

Hotel Strasburg

3.0 star property
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!!!!!!"
Hotel Strasburg
Twi-Lite Inn
Exterior

Twi-Lite Inn

2.0 star property
8.2 out of 10, Very Good, (522)
"Great pool and quiet area to stay in"
The price is ￥10,763
￥11,980 total
includes taxes & fees
Sep 28 - Sep 29
Twi-Lite Inn
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)
"Perfect location to visit for business or pleasure!"
The price is ￥18,933
￥21,450 total
includes taxes & fees
Oct 5 - Oct 6
The George Washington Hotel, A Wyndham Grand Hotel
Red Roof Inn Winchester, VA
Desk, blackout drapes, free cribs/infant beds, free WiFi

Red Roof Inn Winchester, VA

2.0 star property
7.4 out of 10, Good, (1004)
"Staff was very respectful and friendly "
The price is ￥10,463
￥11,383 total
includes taxes & fees
Sep 28 - Sep 29
Red Roof Inn Winchester, VA
Hampton Inn Winchester-University/Mall Area
Porch

Hampton Inn Winchester-University/Mall Area

2.5 star property
9.0 out of 10, Wonderful, (1012)
"Price, Clean!,great breakfast, attention to details and nice room, loved it!"
The price is ￥13,269
￥15,032 total
includes taxes & fees
Oct 13 - Oct 14
Hampton Inn Winchester-University/Mall Area
Clarion Inn & Conference Center
Restaurant

Clarion Inn & Conference Center

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

Sleep Inn & Suites Winchester near University

2.5 star property
7.8 out of 10, Good, (1009)
"Great stay offered a haven on a long trip!"
The price is ￥10,674
￥11,613 total
includes taxes & fees
Oct 26 - Oct 27
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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Find out more about Winchester

Find out more about Winchester

Winchesterand its attractions for luxury travelers

For luxury travelers visiting Winchester, Virginia, the area's rich history and vibrant culture provide a perfect backdrop for an upscale getaway. Start your journey at the Museum of the Shenandoah Valley, where you can explore exquisite art collections and beautifully landscaped gardens that are ideal for a leisurely stroll. Next, indulge in wine tasting at the nearby winery, Shenandoah Valley, which offers picturesque views and exquisite selections—perfect for a romantic afternoon. History enthusiasts will appreciate a guided tour of the historic Old Town, featuring charming boutiques and gourmet restaurants nestled in restored 18th-century buildings. For a unique experience, the Handley Library's stunning architecture and serene reading rooms provide a peaceful retreat for book lovers. Finally, unwind at one of the luxurious hotels in the Historic District, where you can enjoy personalized service, elegant rooms, and convenient access to local attractions. This area not only offers the best of Winchester's cultural experiences but also ensures that your stay is filled with comfort and sophistication.

Find the best luxury hotels and resorts in Winchester

For those seeking an indulgent getaway in Winchester, Virginia, these hotels offer a blend of elegance, comfort, and top-tier amenities to enhance your stay.

The George Washington Hotel, A Wyndham Grand Hotel

  • Why it's great for a luxury retreat: The George Washington Hotel stands out as a premier luxury destination in Old Town Winchester, an impressive guest review rating of 9.4. This exquisite hotel features valet parking and a dedicated concierge service, ensuring that guests receive personalized attention throughout their stay. Premium bedding in each room guarantees restful nights, while the onsite spa offers treatments designed to rejuvenate and pamper travelers seeking relaxation.
  • Other amenities: Guests can enjoy the indoor pool for a refreshing swim or take advantage of the 24-hour fitness facilities to maintain their workout routine. The hotel showcases beautiful Georgian architecture, providing a charming backdrop to your visit. For those looking to explore, nearby skiing and golfing options are available, while daily housekeeping ensures a tidy and comfortable environment. Enjoy complimentary internet access and convenient services like early check-in and late check-out, making every aspect of your stay effortless.
  • Neighborhood: Old Town Winchester
  • Nearby attractions: Handley Regional Library - 0.25 miles, Bright Box Theater - 0.22 miles, Old Court House Civil War Museum - 0.22 miles

Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool is a spectacle to behold! The beauty along with the perfect water temperature provided a perfect ending to our evening!"
Chad 1-night trip
Posted 3 days ago
The George Washington Hotel, A Wyndham Grand Hotel

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Winchester Little Theater. If you have extra time while you're in the area, you might want to see Patsy Cline Historic House and Museum of the Shenandoah Valley.