Find Luxury Hotels in Winchester, VA

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Check availability on Winchester Luxury Hotels

Top Winchester Luxury Hotels

Coffee service
Motel 6 Winchester, VA

Motel 6 Winchester, VA

2.0 star property
Winchester
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • 24/7 front desk
  • Microwave
8.2 out of 10, Very Good, (1000)
Luxury meets practicality in this spotless Winchester retreat. Spacious, modern rooms feature refrigerators and microwaves while the property's standout pet policy welcomes multiple dogs with no weight limit or fees, creating a truly inclusive atmosphere for all travelers.
Motel 6 Winchester, VA
Exterior
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 star property
Winchester
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
8.6 out of 10, Excellent, (1089)
Sophisticated spaces define this welcoming Winchester retreat. Immaculately maintained accommodations feature refrigerators and premium channels for ultimate relaxation. Located steps from Shenandoah University and Valley Health, guests enjoy peaceful surroundings with friendly multilingual staff.
Travelodge by Wyndham Winchester
Bar (on property)
Wayside Inn

Wayside Inn

3.5 star property
Middletown
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
9.2 out of 10, Wonderful, (413)
Housed in a landmark building, this colonial hotel combines rich history with refined indulgence. Individually decorated rooms surround beautiful gardens and terraces. Guests savor delicious cuisine in the dining room while enjoying exceptional service from friendly staff in this peaceful countryside sanctuary.
Wayside Inn
Building design
Hotel Strasburg

Hotel Strasburg

3.0 star property
Strasburg
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
7.8 out of 10, Good, (731)
Housed in a meticulously preserved Victorian building, this historic Strasburg hotel delights with Select Comfort beds in 29 individually decorated rooms. Guests savor complimentary breakfast before exploring nearby Strasburg Museum or unwinding in the lush garden setting.
Hotel Strasburg
Exterior
Twi-Lite Inn

Twi-Lite Inn

2.0 star property
Front Royal
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
8.2 out of 10, Very Good, (536)
Sound-insulated walls create a peaceful haven at this spotlessly maintained motel. Just minutes from Shenandoah River, guests enjoy exceptionally comfortable beds, sparkling pool relaxation, and attentive service from the friendly staff that consistently earns praise from visitors.
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

3.5 star property
Old Town Winchester
  • 2 restaurants
  • Full-service spa
  • Indoor pool
  • Concierge services
9.4 out of 10, Exceptional, (1006)
Sumptuous comfort defines this elegant Winchester landmark. Massages at the full-service spa complement refreshing dips in the indoor pool. Pillowtop beds with premium linens await after exploring nearby museums, while concierge services ensure every luxury desire is fulfilled.
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

2.0 star property
Winchester
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
7.4 out of 10, Good, (1001)
Freshly transformed spaces welcome travelers to this centrally located Winchester retreat. Spotless, spacious rooms feature premium amenities while friendly staff provide attentive service. Pet owners appreciate the complimentary pet policy near shopping, dining and local attractions.
Red Roof Inn Winchester, VA
Porch
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 star property
Winchester
  • Outdoor pool
9.0 out of 10, Wonderful, (1000)
Poolside luxury awaits at this centrally located Winchester hotel. Guests rave about the impeccable service, pristine rooms with comfortable beds, and refreshing outdoor swimming area with sun loungers. Steps from downtown attractions and Shenandoah University.
Hampton Inn Winchester-University/Mall Area
Restaurant
Clarion Inn & Conference Center

Clarion Inn & Conference Center

2.5 star property
Winchester
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
7.8 out of 10, Good, (952)
Sophisticated convenience defines this well-appointed Winchester retreat. Premium accommodations feature kitchenettes and workspaces while a seasonal outdoor pool, fitness center, and on-site restaurant cater to relaxation needs. Just steps from Shenandoah University and local attractions.
Clarion Inn & Conference Center
Lobby
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 star property
Winchester
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Gym
  • Business services
7.8 out of 10, Good, (1001)
Sumptuous down comforters adorn every bed in this refined Winchester retreat. Guests praise the exceptionally quiet atmosphere, spotless accommodations, and attentive service. Minutes from Valley Health and university grounds, this hotel balances luxury touches with practical comforts.
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

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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"The room was very clean, well stocked with towels and the bedding was fresh. Staff was very kind and check in/out went quickly. I also enjoy the breakfasts."
Michele 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

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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.