Explore 19 Luxury Hotels in Winchester

Name: Red Roof Inn Winchester, VA
Price range: $80 total
Rating: 7.4

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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

$122 nightly

$138 total

Mar 23 - Mar 24

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, ...

9.4/10 Exceptional! (1,008 reviews)

Very nice and conveniently located

Reviewed on Mar 16, 2026

Wayside Inn

7783 Main St Middletown VA

$89 nightly

$98 total

Mar 18 - Mar 19

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! (426 reviews)

Nostalgia and history are prime attractions of this lovely inn. The barkeep Justin was friendly and helpful

Reviewed on Mar 16, 2026

Hampton Inn Winchester-University/Mall Area

640 East Jubal Early Drive Winchester VA

Fully refundableReserve now, pay when you stay

$102 nightly

$115 total

Mar 29 - Mar 30

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! (1,002 reviews)

Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel

Reviewed on Mar 15, 2026

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

Fully refundableReserve now, pay when you stay

$68 nightly

$74 total

Mar 19 - Mar 20

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 ...

8.6/10 Excellent! (1,075 reviews)

Best quality around the area.

Reviewed on Mar 17, 2026

Motel 6 Winchester, VA

2951 Valley Avenue Winchester VA

Fully refundableReserve now, pay when you stay

$68 nightly

$77 total

Mar 19 - Mar 20

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 ...

8.2/10 Very Good! (1,001 reviews)

Room clean and staff was nice

Reviewed on Feb 25, 2026

Twi-Lite Inn

53 West 14th Street Front Royal VA

Fully refundableReserve now, pay when you stay

$72 nightly

$80 total

Mar 18 - Mar 19

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 ...

8.2/10 Very Good! (547 reviews)

Staff were nice, room was clean, and checkout was a breeze. They made it simple by telling us to just leave the room key on the dresser. There was no need to turn it into the office.

Reviewed on Mar 10, 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

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Red Roof Inn Winchester, VA

991 Millwood Pike Winchester VA

Fully refundableReserve now, pay when you stay

$73 nightly

$80 total

Mar 18 - Mar 19

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! (1,002 reviews)

Good app

Reviewed on Mar 15, 2026

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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

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10/10 Exceptional! (4 reviews)

5 star hotels in Winchester

Salamander Resort And Spa

500 North Pendleton Street Middleburg VA

$621 nightly

$707 total

Apr 5 - Apr 6

Total with taxes and fees

9.2/10 Wonderful! (384 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	2,045 hotels
Lowest Price	$74
Highest Price	$707
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