Find a Hotel in Old Town Winchester

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Top hotels in Old Town Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free self-serve breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
"Clean room and spacious"

Reviewed on Oct 5, 2025

Opens in a new windowComfort Inn & Suites 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
$127 nightly
The price is $144 total per night from Oct 23 to Oct 24
$144 total
Oct 23 - Oct 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, ...
"I’d return for sure. Our room was wonderful."

Reviewed on Oct 10, 2025

Opens in a new windowThe George Washington Hotel, A Wyndham Grand Hotel
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
$103 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
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 ...
"Nice hotel"

Reviewed on Oct 10, 2025

Opens in a new windowLa Quinta Inn & Suites by Wyndham Winchester
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
$114 nightly
The price is $129 total per night from Oct 26 to Oct 27
$129 total
Oct 26 - Oct 27
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 ...
"Great stay! Would definitely would stay again!"

Reviewed on Oct 10, 2025

Opens in a new windowHampton Inn Winchester-University/Mall Area
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
$82 nightly
The price is $89 total per night from Nov 9 to Nov 10
$89 total
Nov 9 - Nov 10
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 place good price"

Reviewed on Oct 6, 2025

Opens in a new windowMicrotel Inn & Suites by Wyndham Winchester
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd, Front Royal, VA
$106 nightly
The price is $118 total per night from Nov 9 to Nov 10
$118 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...
"Friendly staff and good breakfast."

Reviewed on Oct 6, 2025

Opens in a new windowHampton Inn Front Royal
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Fully refundable
$91 nightly
The price is $99 total per night from Nov 9 to Nov 10
$99 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
"Perfect stop over on our road trip. Clean with friendly staff. Breakfast was great with waffle machines!"

Reviewed on Oct 8, 2025

Opens in a new windowCountry Inn & Suites by Radisson, Winchester, VA
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $75 total per night from Oct 20 to Oct 21
$75 total
Oct 20 - Oct 21
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 ...
"It was ok"

Reviewed on Oct 12, 2025

Opens in a new windowTravelodge by Wyndham Winchester
Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry

2 out of 5
642 E Washington Street, Charles Town, WV
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $73 total per night from Oct 19 to Oct 20
$73 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free area shuttle. Traveling on business? Take advantage ...
"I"

Reviewed on Oct 12, 2025

Opens in a new windowDays Inn by Wyndham Charles Town/Harpers Ferry
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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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