Find luxury hotels in Winchester, VA

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Luxury Hotels

This weekend
Next weekend

Our top choices for Winchester luxury hotels

Motel 6 Winchester, VA

Motel 6 Winchester, VA
2.0 star property
Winchester
8.2 out of 10, Very good, (1,000 reviews)
"It was clean and in a safe area "
United States
Daryl
The price is £57
includes taxes & fees
7 Mar - 8 Mar
Motel 6 Winchester, VA

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,078 reviews)
"Clean place, breakfast ok, warm and comfy, would stay again"
United States
Lyle
The price is £56
includes taxes & fees
6 Mar - 7 Mar
Travelodge by Wyndham Winchester

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (424 reviews)
"Room 14 was great for spirit activity as well as the rest of the property! Highly recommend ghost hunters to explore the inn. Food at their Larick’s tavern was delish!! Overall service and staff were knowledgeable and friendly! We had a great experience for our anniversary! "
United States
Megan
The price is £67
includes taxes & fees
5 Mar - 6 Mar
Wayside Inn

Hotel Strasburg

Hotel Strasburg
3.0 star property
Strasburg
7.8 out of 10, Good, (731 reviews)
"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

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very good, (546 reviews)
"Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay"
United States
Daniel
The price is £60
includes taxes & fees
5 Mar - 6 Mar
Twi-Lite Inn

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, (1,006 reviews)
"Great hotel!"
United States
CHARLES
The price is £103
includes taxes & fees
10 Mar - 11 Mar
The George Washington Hotel, A Wyndham Grand Hotel

Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA
2.0 star property
Winchester
7.4 out of 10, Good, (1,001 reviews)
"Clean, pet friendly and great check in."
United States
Anita Willsie
The price is £56
includes taxes & fees
1 Apr - 2 Apr
Red Roof Inn Winchester, VA

Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"Pet friendly and they provided a goodie bag for my dog - very welcoming."
Canada
Kimberly
The price is £86
includes taxes & fees
29 Mar - 30 Mar
Hampton Inn Winchester-University/Mall Area

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1,001 reviews)
"Everything was fine "
United States
Terence
The price is £65
includes taxes & fees
2 Apr - 3 Apr
Sleep Inn & Suites Winchester near University

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2,283 reviews)
"Very Friendly staff and clean rooms! "
United States
Kayla
The price is £89
includes taxes & fees
8 Mar - 9 Mar
La Quinta Inn & Suites by Wyndham Winchester
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.

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.

Find out more about Winchester

Winchesterand its attractions for luxury travelers

For luxury travellers seeking an enriching experience in Winchester, Virginia, the historic charm of the town is complemented by several exquisite attractions. Begin your exploration at the picturesque Old Town, where cobblestone streets are lined with boutique shops and gourmet restaurants, perfect for indulging in fine dining or unique shopping. The Museum of the Shenandoah Valley offers a stunning blend of art and history, with beautiful gardens and engaging exhibits that provide a glimpse into the region's rich past. For those who enjoy the great outdoors, the serene beauty of the nearby Shenandoah National Park invites leisurely hikes and breathtaking views, enhancing your stay with nature's splendour. A visit to the Apple Blossom Mall offers a touch of retail therapy, featuring high-end brands and designer stores that cater to discerning shoppers. After a day of exploration, unwind in one of Winchester's luxury hotels, such as the George Washington Hotel, which boasts elegant rooms, a full-service spa, and fine dining options, ensuring a pampered experience. Staying in the heart of Old Town not only allows you to easily access these attractions but also provides a vibrant atmosphere that captures the essence of Winchester, making your visit both memorable and luxurious.

Find the best luxury hotels and resorts in Winchester

For travelers seeking a touch of elegance in Winchester, these hotels offer a perfect blend of luxury and comfort, ensuring an unforgettable stay.

The George Washington Hotel, A Wyndham Grand Hotel

  • Why it's great for a luxury retreat: The George Washington Hotel stands as a beacon of luxury in Old Town Winchester, with an impressive guest review rating of 9.4. This exquisite hotel features premium bedding for a restful night's sleep and offers valet parking for added convenience. Guests can indulge in the onsite spa, which provides a full range of treatments, ensuring complete relaxation during their stay.
  • Other amenities: The hotel boasts a stunning Georgian design that adds to its charm and elegance. Guests can enjoy an indoor pool, a well-equipped fitness centre available 24 hours, and the option for contactless check-in for a seamless arrival experience. Daily housekeeping keeps the rooms pristine, while the option for late check-out allows for a leisurely departure. Additionally, the hotel's nearby golf, hiking, and skiing ensures that adventurers can easily explore the beautiful surroundings.
  • Neighborhood: Old Town Winchester
  • Nearby attractions: Handley Regional Library - 0.4 km, Bright Box Theater - 0.4 km, Old Court House Civil War Museum - 0.4 km

Top Winchester Hotel Reviews

Frequently asked questions

Which area of Winchester is best to stay in for luxury hotels?
The best area of Winchester for luxury hotels is Historic Old Town, particularly around the Loudoun Street Mall.

This area is the heart of Winchester, known for its pedestrian-only walking mall, which is a key feature. Here, you'll find beautifully preserved 18th and 19th-century architecture, independent shops, and a wide array of restaurants and cafes. The district is very walkable, making it easy to stroll between attractions like the Handley Regional Library and the Old Court House Civil War Museum.

For couples seeking a refined and convenient stay, Historic Old Town is an excellent choice. The location provides easy access to romantic dinners, leisurely walks, and the chance to explore local history and culture without needing a car.
How much does a luxury hotel in Winchester cost?
Luxury hotel prices in Winchester vary, but you can find a great deal from £56 on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates.
How can I save on a luxury hotel in Winchester with Expedia?
There are plenty of ways to save on a luxury hotel in Winchester. Join One Key™, our free travel rewards programme, to unlock Member Prices across a range of hotels. Typically, booking in advance will help you save on hotel bookings. If you're feeling spontaneous, be sure to check for last-minute deals.
Is it cheaper to book a luxury Winchester hotel and flights as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
Can I cancel my luxury hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right luxury hotel in Winchester for you.

Explore a world of travel with Expedia