Explore 19 Luxury Hotels in Winchester

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Best Luxury Hotels in Winchester

Wayside Inn

7783 Main St, Middletown, VA

$107 nightly

$118 total

Aug 3 - Aug 4

Total includes taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking, a ...

9.2/10 Wonderful! (391 reviews)

"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere."

Reviewed on Jul 7, 2025

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester, VA

Fully refundableReserve now, pay when you stay

$127 nightly

$144 total

Jul 27 - Jul 28

Total includes taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...

9.2/10 Wonderful! (1,002 reviews)

"Hotel was very nice. Service was good and it was clean and convenient."

Reviewed on Jul 14, 2025

Hampton Inn Winchester-University/Mall Area

640 East Jubal Early Drive, Winchester, VA

Fully refundableReserve now, pay when you stay

$109 nightly

$124 total

Aug 3 - Aug 4

Total includes taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...

9/10 Wonderful! (1,001 reviews)

"The hotel was near to Shenandoah University."

Reviewed on Jul 20, 2025

Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester, VA

Fully refundableReserve now, pay when you stay

$69 nightly

$75 total

Jul 27 - Jul 28

Total includes taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. There's express check-out and multilingual staff can provide around-the-clock ...

8.4/10 Very Good! (1,094 reviews)

"This was a perfect one night stop on my road trip. The room was large and clean. However, I think the cleaner they use for the floor leaves a residue. I dared to walk on it barefoot and it was a tad slippery, so I recommend wearing slippers. It was quiet and pet friendly! There is a $15 pet fee."

Reviewed on Jul 21, 2025

Motel 6 Winchester, VA

2951 Valley Avenue, Winchester, VA

Fully refundableReserve now, pay when you stay

$64 nightly

$73 total

Jul 27 - Jul 28

Total includes taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock ...

8/10 Very Good! (1,003 reviews)

"Staff is friendly yet professional. I travel with my service dog and they make a big fuss over her with treats and kindness. Nothing better than having animal lovers run a clean, safe and affordable motel."

Reviewed on Jul 20, 2025

Twi-Lite Inn

53 West 14th Street, Front Royal, VA

Fully refundableReserve now, pay when you stay

$78 nightly

$87 total

Jul 28 - Jul 29

Total includes taxes and fees

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock ...

8/10 Very Good! (513 reviews)

"Good"

Reviewed on Jul 22, 2025

Red Roof Inn Winchester, VA

991 Millwood Pike, Winchester, VA

Fully refundableReserve now, pay when you stay

$70 nightly

$76 total

Jul 27 - Jul 28

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Free parking, express check-in, and express check-out are also ...

7.4/10 Good! (1,002 reviews)

Great night stay

"Really friendly staff, room was clean and perfect for our family and dog."

Reviewed on Jul 20, 2025

Hotel Strasburg

213 S. Holliday Street, Strasburg, VA

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...

awful

"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!!!!!!"

Reviewed on Oct 5, 2020

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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.

More 4 star hotels in Winchester

Guest House at Mt. Independence

2254 Winchester Rd, Delaplane, VA

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10/10 Exceptional! (4 reviews)

5 star hotels in Winchester

Salamander Resort And Spa

500 North Pendleton Street, Middleburg, VA

$693 nightly

$790 total

Aug 13 - Aug 14

Total includes taxes and fees

9/10 Wonderful! (359 reviews)

Winchester Luxury Hotels

Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the Winchester luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in Winchester to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.

We want you to enjoy your next vacation in style and the top luxury resorts in Winchester will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Winchester, and plan your next opulent escape.

Winchester hotels essential information

Accommodation	1,998 hotels
Lowest Price	$73
Highest Price	$790
Popular hotels	Motel 6 Winchester, VA, Travelodge by Wyndham Winchester, Wayside Inn, Hotel Strasburg, Twi-Lite Inn, The George Washington Hotel, A Wyndham Grand Hotel, Red Roof Inn Winchester, VA, Hampton Inn Winchester-University/Mall Area