Explore 19 Luxury Hotels in Winchester
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Best Luxury Hotels in Winchester
Wayside Inn
7783 Main St, Middletown, VA
$129 nightly
The price is $142 total per night from Nov 9 to Nov 10
$142 total
Nov 9 - Nov 10
Total with taxes and fees
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! (399 reviews)
Historic inn.
Reviewed on Oct 20, 2025
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $144 total per night from Oct 30 to Oct 31
$144 total
Oct 30 - Oct 31
Total with 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! (1,014 reviews)
Wonderful stay.
Reviewed on Oct 17, 2025
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $115 total per night from Nov 3 to Nov 4
$115 total
Nov 3 - Nov 4
Total with 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! (1,000 reviews)
Parking area felt very safe. Fruit available for breakfast.
Reviewed on Oct 21, 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $75 total per night from Nov 2 to Nov 3
$75 total
Nov 2 - Nov 3
Total with 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! (1,097 reviews)
Friendly staff
Reviewed on Oct 19, 2025
Motel 6 Winchester, VA
2951 Valley Avenue, Winchester, VA
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $77 total per night from Oct 26 to Oct 27
$77 total
Oct 26 - Oct 27
Total with 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! (1,008 reviews)
Traling
Staff friendly
Reviewed on Oct 18, 2025
Twi-Lite Inn
53 West 14th Street, Front Royal, VA
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Nov 2 to Nov 3
$85 total
Nov 2 - Nov 3
Total with 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! (528 reviews)
yes and yes
Reviewed on Oct 19, 2025
Red Roof Inn Winchester, VA
991 Millwood Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $70 total per night from Nov 1 to Nov 2
$70 total
Nov 1 - Nov 2
Total with 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! (1,000 reviews)
Good Stay
Good stay for an overnight trip. Kumar treated us like very special people! Clean and very comfortable. Only problem - ADA shower very difficult to use for someone less then 5’4. Reaching the shower head was impossible. Would not recommend this place for special needs.
Reviewed on Oct 22, 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
Guest House at Mt. Independence
2254 Winchester Rd, Delaplane, VA
10/10 Exceptional! (4 reviews)
5 star hotels in Winchester
Salamander Resort And Spa
500 North Pendleton Street, Middleburg, VA
$571 nightly
The price is $650 total per night from Oct 30 to Oct 31
$650 total
Oct 30 - Oct 31
Total with taxes and fees
9/10 Wonderful! (364 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 | 2,021 hotels |
|---|---|
Lowest Price | $70 |
Highest Price | $650 |
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
"Clean room, friendly staff"
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Winchester
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