Explore 19 Luxury Hotels in Winchester
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Best Luxury Hotels in Winchester
Wayside Inn
7783 Main St Middletown VA
The price is $98 total per night from Dec 8 to Dec 9
$98 total
per night
Dec 8 - Dec 9
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! (406 reviews)
Brittany and the rest of the staff at Wayside were wonderful. They made us feel welcome, talked to us about the history and quirks of the, and our room was very quaint. The Christmas decorations in the room were a nice touch.
Reviewed on Nov 23, 2025
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
The price is $143 total per night from Dec 14 to Dec 15
$143 total
per night
Dec 14 - Dec 15
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! (1,003 reviews)
Great hotel and staff
Reviewed on Dec 4, 2025
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive Winchester VA
Fully refundableReserve now, pay when you stay
The price is $112 total per night from Jan 4 to Jan 5
$112 total
per night
Jan 4 - Jan 5
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)
Room was quiet and comfy and staff were friendly! Entry way was decorated for the holidays!
Reviewed on Dec 1, 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is $74 total per night from Dec 22 to Dec 23
$74 total
per night
Dec 22 - Dec 23
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! (1,075 reviews)
Très très bien déjeuné wow depuis 20 ans que je passe par la ils s'améliore toujours
Reviewed on Dec 5, 2025
Motel 6 Winchester, VA
2951 Valley Avenue Winchester VA
Fully refundableReserve now, pay when you stay
The price is $77 total per night from Dec 8 to Dec 9
$77 total
per night
Dec 8 - Dec 9
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)
Good area
Reviewed on Nov 26, 2025
Twi-Lite Inn
53 West 14th Street Front Royal VA
Fully refundableReserve now, pay when you stay
The price is $69 total per night from Dec 8 to Dec 9
$69 total
per night
Dec 8 - Dec 9
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! (539 reviews)
Room was very clean. Easy, efficient check-in, quiet, very comfortable beds.
Reviewed on Nov 23, 2025
Red Roof Inn Winchester, VA
991 Millwood Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is $66 total per night from Jan 1 to Jan 2
$66 total
per night
Jan 1 - Jan 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 ...
7.2/10 Good! (1,001 reviews)
Just what you expect from Red Roof Inn. Things are a little beat up, but most things work and you get a place to stay with no bugs, and no pet fee
Reviewed on Nov 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
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! (9 reviews)
5 star hotels in Winchester
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
The price is $666 total per night from Dec 16 to Dec 17
$666 total
per night
Dec 16 - Dec 17
9.2/10 Wonderful! (370 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 | 2,034 hotels |
|---|---|
Lowest Price | $66 |
Highest Price | $666 |
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
Travelodge by Wyndham Winchester
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Très très bien déjeuné wow depuis 20 ans que je passe par la ils s'améliore toujours "
A verified traveler stayed at Travelodge by Wyndham Winchester
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