Explore 19 Luxury Hotels in Winchester
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Best Luxury Hotels in Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
The price is $138 total per night from Jun 21 to Jun 22
$138 total
per night
Jun 21 - Jun 22
A full-service spa, 2 restaurants, and an indoor pool are all featured at this Georgian hotel. Traveling on business? Take advantage of the business center, ...
9.4/10 Exceptional! (1,006 reviews)
"Check in and check out staff were very nice and gave good recommendations about local eateries. Room was clean, easy to control thermostat that maintained temperature. Shower was AMAZING!! Water pressure was great and nice hot shower, best part of the room. Lobby was nice to hang out in as well. ..."
Reviewed on Jun 14, 2026
Wayside Inn
7783 Main St Middletown VA
The price is $159 total per night from Jun 16 to Jun 17
$159 total
per night
Jun 16 - Jun 17
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Free parking, a terrace, and a garden are also offered.
9.2/10 Wonderful! (437 reviews)
"Clean, well-maintained, delicious food, hot shower!"
Reviewed on Jun 7, 2026
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive Winchester VA
Fully refundableReserve now, pay when you stay
The price is $106 total per night from Jul 1 to Jul 2
$106 total
per night
Jul 1 - Jul 2
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! (1,000 reviews)
"Overall excellent stay. Friendly staff. Great breakfast. Easy access to I-81. The only thing I could complain about was the gym. The 2 treadmills were out of order and the bike and "walker/xcountry ski" machines both required a login with Peloton to use. But lots of weights to use. Would definitely ..."
Reviewed on Jun 1, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is $77 total per night from Jun 16 to Jun 17
$77 total
per night
Jun 16 - Jun 17
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 ...
8.6/10 Excellent! (1,067 reviews)
"My favorite place to stay"
Reviewed on Jun 14, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
The price is $91 total per night from Jun 30 to Jul 1
$91 total
per night
Jun 30 - Jul 1
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 ...
8.2/10 Very Good! (558 reviews)
"Very old and outdated place"
Reviewed on Jun 14, 2026
Motel 6 Winchester, VA
2951 Valley Avenue Winchester VA
Fully refundableReserve now, pay when you stay
The price is $86 total per night from Jun 16 to Jun 17
$86 total
per night
Jun 16 - Jun 17
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! (1,007 reviews)
"very pet friendly, large area for dogs, well lighted parking"
Reviewed on Jun 9, 2026
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 ...
7.8/10 Good! (731 reviews)
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
Red Roof Inn Winchester, VA
991 Millwood Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is $75 total per night from Jul 1 to Jul 2
$75 total
per night
Jul 1 - Jul 2
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! (1,008 reviews)
"When we checked in there were several issues with the room. We were told they would be corrected the next day, but they were not. There was trash and cigarette butts throughout the parking area and grass."
Reviewed on Jun 8, 2026
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
10/10 Exceptional! (10 reviews)
5 star hotels in Winchester
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
The price is $790 total per night from Jun 23 to Jun 24
$790 total
per night
Jun 23 - Jun 24
9.2/10 Wonderful! (399 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 | 2,081 hotels |
|---|---|
Lowest Price | $75 |
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 |
Popular Luxury Stays in Winchester
Recent Winchester Hotel Reviews By Fellow Wanderers
La Quinta Inn & Suites by Wyndham Winchester
4 out of 5
Posted 3 hours ago
Travelocity Verified Review
"very well presented and lived up to it very pleased"
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Winchester
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