Explore 19 Luxury Hotels in Winchester

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Best Luxury Hotels in Winchester

Wayside Inn

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

Opens in a new windowWayside Inn
The George Washington Hotel, A Wyndham Grand Hotel

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

Opens in a new windowThe George Washington Hotel, A Wyndham Grand Hotel
Hampton Inn Winchester-University/Mall Area

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

Opens in a new windowHampton Inn Winchester-University/Mall Area
Travelodge by Wyndham Winchester

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

Opens in a new windowTravelodge by Wyndham Winchester
Motel 6 Winchester, VA

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

Opens in a new windowMotel 6 Winchester, VA
Twi-Lite Inn

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

Opens in a new windowTwi-Lite Inn
Red Roof Inn Winchester, VA

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

Opens in a new windowRed Roof Inn Winchester, VA
Hotel Strasburg

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

Opens in a new windowHotel Strasburg
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5 star hotels in Winchester

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

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