A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Luxury Hotels & Resorts in Winchester from NZ$169

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Check availability on Winchester Luxury Hotels

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Winchester luxury hotels

1. Hillbrook Inn

Hillbrook Inn
Charles Town
NZ$342
includes taxes & fees
3 Nov - 4 Nov
Hillbrook Inn

2. White Moose Inn

White Moose Inn
Washington
NZ$562
includes taxes & fees
18 Oct - 19 Oct
White Moose Inn

3. Hotel Burg

Hotel Burg
Leesburg's Old and Historic District
NZ$515
includes taxes & fees
1 Nov - 2 Nov
Hotel Burg

4. Salamander Middleburg

Salamander Middleburg
Middleburg
  • Indulge in five-star luxury at this historical district resort featuring 14 treatment rooms, two gourmet restaurants, and hot springs.
NZ$1,480
includes taxes & fees
29 Oct - 30 Oct
Salamander Middleburg

5. Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath

Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
Augusta
Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath

6. 1987 “OAK SPRINGS”- Majestic-Tranquil-Serene…

1987 “OAK SPRINGS”- Majestic-Tranquil-Serene…
Luray
NZ$486
includes taxes & fees
8 Nov - 9 Nov
1987 “OAK SPRINGS”- Majestic-Tranquil-Serene…

7. River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B

River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Berkeley Springs
NZ$521
includes taxes & fees
8 Nov - 9 Nov
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
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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 discerning travellers seeking a touch of elegance in Winchester, these luxurious hotels offer a sophisticated retreat with exceptional amenities and services.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 for travellers in Winchester, an impressive guest review rating of 9.4. This exquisite hotel offers valet parking and a dedicated concierge service, ensuring a seamless and personalised experience for each guest. The premium bedding guarantees restful nights, while the onsite spa and indoor pool provide the perfect escape for relaxation and rejuvenation.
  • Other amenities: Guests can indulge in a range of additional features, including a 24-hour fitness centre, complimentary internet, and early check-in or late check-out options for added convenience. The hotel showcases its Georgian hotel design, exuding historical charm while accommodating modern luxuries. With daily housekeeping, free toiletries, and in-room massage services, every detail is thoughtfully catered to enhance your stay. For those who enjoy outdoor activities, the hotel is ideally located near skiing, golfing, and hiking opportunities.
  • 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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Staff is always very pleasant to work with."
Lisa 2-night trip
Posted 6 hours ago
Travelodge by Wyndham Winchester
Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

10/10 Excellent
"Great place to stay in Luray."
Eric 1-night trip
Posted 1 day ago
Mimslyn Inn Historic Hotels Of America
Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"Very nice room. Very clean."
Rebecca 1-night trip
Posted 2 days ago
Spark by Hilton Winchester
Skyland

Skyland

10/10 Excellent
"Wonderful stay. Cabin was clean and bed was comfortable."
Donna 2-night trip
Posted 4 days ago
Skyland

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 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.

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