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Top hotels in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $138 total per night from Mar 22 to Mar 23
$138 total
Mar 22 - Mar 23
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, ...
Great stay!

Reviewed on Mar 15, 2026

Opens in a new windowThe George Washington Hotel, A Wyndham Grand Hotel
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 out of 5
280 MARKET STREET Winchester VA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $114 total per night from Mar 22 to Mar 23
$114 total
Mar 22 - Mar 23
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
Have stayed at a SpringHill Suites several times at various locations and I am never disappointed. Always clean, always comfortable, and the staff is always pleasant

Reviewed on Mar 15, 2026

Opens in a new windowSpringHill Suites by Marriott Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $123 total per night from Mar 18 to Mar 19
$123 total
Mar 18 - Mar 19
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
Not your average hotel. Unique room layout, modern lobby and friendly staff!

Reviewed on Mar 15, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $92 total per night from Mar 22 to Mar 23
$92 total
Mar 22 - Mar 23
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests ...
Clean rooms.

Reviewed on Mar 7, 2026

Opens in a new windowMicrotel Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
Fully refundable
$91 nightly
The price is $99 total per night from Apr 12 to Apr 13
$99 total
Apr 12 - Apr 13
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
Very clean, nice bar/restaurant, convenient location. Excellent breakfast! Will definitely stay again when traveling 😄

Reviewed on Mar 14, 2026

Opens in a new windowHoliday Inn Winchester Se-Historic Gateway by IHG
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive Winchester VA
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $115 total per night from Mar 22 to Mar 23
$115 total
Mar 22 - Mar 23
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 ...
Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel

Reviewed on Mar 15, 2026

Opens in a new windowHampton Inn Winchester-University/Mall Area
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3 out of 5
300 Marriott Drive Winchester VA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $116 total per night from Mar 22 to Mar 23
$116 total
Mar 22 - Mar 23
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
Great location

Reviewed on Mar 15, 2026

Opens in a new windowCourtyard by Marriott Winchester
The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

3 out of 5
100 Hollywood Dr Charles Town WV
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $131 total per night from Mar 17 to Mar 18
$131 total
Mar 17 - Mar 18
Total with taxes and fees
A casino, 4 restaurants, and a gym are all featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
The A/C was awesome!! The room was very clean. The hallways were quiet. Really enjoyed the shuttle to the casino

Reviewed on Mar 15, 2026

Opens in a new windowThe Inn at Charles Town - Hollywood Casino
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr Winchester VA
Fully refundable
$80 nightly
The price is $87 total per night from Apr 5 to Apr 6
$87 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business ...
This is the dirtiest hotel I’ve ever stayed at. There was an earwig in the bathroom. The bed cover was dirty, everything was dingy. The walls, the chair. The one side of the mattress springs were so wore and broken. The plug in the bathroom didn’t work. The handicap bar was out of the wall. You can ...

Reviewed on Mar 15, 2026

Opens in a new windowSleep Inn & Suites Winchester near University
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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.

Old Town Winchester Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Old Town Winchester area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Old Town Winchester to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Old Town Winchester are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

Recent Old Town Winchester hotel reviews by fellow wanderers

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