Find a Hotel in Old Town Winchester

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

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
$101 nightly
The price is $110 total per night from Nov 21 to Nov 22
$110 total
Nov 21 - Nov 22
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 ...
Front desk staff was great!

Reviewed on Nov 7, 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 $143 total per night from Nov 18 to Nov 19
$143 total
Nov 18 - Nov 19
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 was very pleased with the accommodations at this hotel. I can't stress enough how incredible the pool is. The hot tub is great too, but I was impressed with the pool and would visit again just for that. Make sure to check that out!

Reviewed on Oct 31, 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
$105 nightly
The price is $115 total per night from Dec 10 to Dec 11
$115 total
Dec 10 - Dec 11
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 ...
Clean room

Reviewed on Nov 8, 2025

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
$78 nightly
The price is $84 total per night from Nov 23 to Nov 24
$84 total
Nov 23 - Nov 24
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 ...
Excellent accommodations

Reviewed on Nov 7, 2025

Opens in a new windowMicrotel 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
$103 nightly
The price is $117 total per night from Nov 18 to Nov 19
$117 total
Nov 18 - Nov 19
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 ...
Clean, great design, nice staff

Reviewed on Nov 10, 2025

Opens in a new windowHampton Inn Winchester-University/Mall Area
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
$73 nightly
The price is $79 total per night from Nov 16 to Nov 17
$79 total
Nov 16 - Nov 17
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 ...
Clean, nice breaksfast service

Reviewed on Nov 4, 2025

Opens in a new windowHoliday Inn Winchester Se-Historic Gateway by IHG
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
$97 nightly
The price is $105 total per night from Dec 2 to Dec 3
$105 total
Dec 2 - Dec 3
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 ...
Good

Reviewed on Nov 7, 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
$68 nightly
The price is $74 total per night from Dec 1 to Dec 2
$74 total
Dec 1 - Dec 2
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 ...
Such a great find for our overnight Stay and last minute with excellent price. Comfortable bed and fantastic staff. Breakfast lacking but expected.

Reviewed on Nov 6, 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
$70 nightly
The price is $79 total per night from Nov 16 to Nov 17
$79 total
Nov 16 - Nov 17
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 ...
All in all, the stay was good and I would stay there again.The location was close to the Village of Appomatox. The rooms were clean except for stains on the floor and chairs. The breakfast that was advertised wasn't fantastic. It was cold cereal and a bit of fruit.

Reviewed on Oct 26, 2025

Opens in a new windowDays Inn by Wyndham Charles Town/Harpers Ferry
Don't see what you're looking for?
See all available properties in Old Town Winchester
View all properties
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

Explore More Ways to Travel with Travelocity