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Check prices on hotels in Winchester

Tonight 20 May - 21 May
This weekend 24 May - 26 May
Next weekend 31 May - 2 Jun.

Featured Winchester 5 Stars Hotels

See all 452 properties in Winchester

Estimated price for 1 night/2 adults

Salamander Resort And Spa
Salamander Resort And Spa
5.0 out of 5.0 500 North Pendleton Street, Middleburg, VA
Free Cancellation
4.6/5 (128 reviews)
C$626/ night for 2 guests

Everything about Salamander is absolutely fabulous!

Reviewed on 1 Apr. 2019
The Inn At Little Washington
The Inn At Little Washington
5.0 out of 5.0 Middle And Main Streets, Washington, VA
Free Cancellation
4.9/5 (40 reviews)
C$1,252/ night for 2 guests

Wonderful property. Included tea and breakfast were top notch.

Reviewed on 9 Feb. 2019
Celebration Retreat
Celebration Retreat
5.0 out of 5.0 440 Scenic Overlook Dr, Front Royal, VA
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Five Star Hotels in Winchester

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Winchester so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Winchester and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Winchester

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Winchester

The results are in, and Winchester 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Winchester! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winchester today and settle down in the lap of luxury tomorrow.

Recently booked Winchester hotels

Courtyard by Marriott Winchester
3.0 out of 5.0
Last booking: 1 hour ago
Ramada by Wyndham Strasburg
2.5 out of 5.0
Last booking: 1 hour ago
Travelodge by Wyndham Winchester
2.0 out of 5.0
Last booking: 2 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5.0
Last booking: 2 hours ago
La Quinta by Wyndham Winchester
3.0 out of 5.0
Last booking: 3 hours ago
Hotel Strasburg
3.0 out of 5.0
Last booking: 12 hours ago
Hampton Inn Front Royal
2.5 out of 5.0
Last booking: 12 hours ago
Country Inn & Suites by Radisson, Winchester, VA
3.0 out of 5.0
Last booking: 12 hours ago
Hilton Garden Inn Winchester
3.0 out of 5.0
Last booking: 13 hours ago