Explore 19 Luxury Hotels in Winchester

Best Luxury Hotels in Winchester

Wayside Inn

7783 Main St, Middletown, VA

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! (386 reviews)

"If your history buff exploring the area this is your ideal base of operations. Close to many local historical sites and the place itself is a piece of Americana. If the walls could talk in this place who knows what it would tell us about the past. The place is remarkably well kept given its age and ..."

Reviewed on Jun 17, 2025

Get rates

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester, VA

Fully refundableReserve now, pay when you stay

A full-service spa, 2 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...

9.2/10 Wonderful! (1,000 reviews)

"Great staff. Great location. Got nice quiet and spacious room. Easy walks to history, food and drink."

Reviewed on Jun 14, 2025

Get rates

Hampton Inn Winchester-University/Mall Area

640 East Jubal Early Drive, Winchester, VA

Fully refundableReserve now, pay when you stay

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! (1,002 reviews)

"Excellent"

Reviewed on Jun 20, 2025

Get rates

Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester, VA

Fully refundableReserve now, pay when you stay

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 ...

8.2/10 Very Good! (1,104 reviews)

"Very clean and eco-friendly…. Loved the waffles for breakfast!!!! Super bonus!!!"

Reviewed on Jun 21, 2025

Get rates

Motel 6 Winchester, VA

2951 Valley Avenue, Winchester, VA

Fully refundableReserve now, pay when you stay

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! (1,001 reviews)

"Comfortable enough, clean room."

Reviewed on Jun 21, 2025

Get rates

Twi-Lite Inn

53 West 14th Street, Front Royal, VA

Fully refundableReserve now, pay when you stay

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! (509 reviews)

"This is such a delightful Inn run by lovely people. Is it a 5 star hotel? No. Was it built in the 70s? Probably. Nonetheless, the pool is crystal clear. The landscaping is gorgeous (The gentleman does it all himself!) Its close to a beautiful state park. The owners couldnt be more friendly. I've ..."

Reviewed on Jun 22, 2025

Get rates

Red Roof Inn Winchester, VA

991 Millwood Pike, Winchester, VA

Fully refundableReserve now, pay when you stay

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)

"Choose it because we read it had been renovated recently and we prefer the option of parking our truck right outside our room. Easily met those expectations. Saw reviews in the past about bed bugs but we saw no evidence of bugs in the two bottom floor rooms we rented. Hot coffee was available in ..."

Reviewed on Jun 18, 2025

Get rates

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

Get rates

Don't see what you're looking for?

See all available properties in Winchester

View all properties

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

South Court Inn

160 S Court St, Luray, VA

Get rates

10/10 Exceptional! (8 reviews)

5 star hotels in Winchester

Salamander Resort And Spa

500 North Pendleton Street, Middleburg, VA

Get rates

9/10 Wonderful! (355 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	1,989 hotels
Lowest Price
Highest Price
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

Popular Luxury Stays in Winchester

Recent Winchester Hotel Reviews By Fellow Wanderers

La Quinta Inn & Suites by Wyndham Winchester

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"I was traveling by motorcycle. I arrived early due to a massive storm that was about to hit. They let me check in an hour early. Super cool of them!"

A verified traveler stayed at La Quinta Inn & Suites by Wyndham Winchester