Find a Hotel in Old Town Winchester

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
Property amenities
Property amenities
Accessibility
Accessibility

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 26 to Mar 27
$138 total
Mar 26 - Mar 27
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, ...
Location of hotel is great for walking to restaurants and shops.

Reviewed on Mar 18, 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 26 to Mar 27
$114 total
Mar 26 - Mar 27
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 ...
Just overall EXCELLENT

Reviewed on Mar 17, 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
$107 nightly
The price is $117 total per night from Mar 22 to Mar 23
$117 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 business center and free WiFi in public areas. Guests will appreciate ...
Nice room, friendly staff

Reviewed on Mar 17, 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 ...
Quick over night while traveling. Everything we needed

Reviewed on Mar 19, 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 19 to Apr 20
$99 total
Apr 19 - Apr 20
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 ...
Yes

Reviewed on Mar 18, 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 29 to Mar 30
$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 ...
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 26 to Mar 27
$116 total
Mar 26 - Mar 27
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. ...
Bed very comfortable, restaurant has very limited bar food , expensive for what you get. The shower in the morning was dribbling and not sufficient to use. Half the water dribbled from the tub faucet and thus shower had to pressure .

Reviewed on Mar 18, 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
$129 nightly
The price is $144 total per night from Mar 23 to Mar 24
$144 total
Mar 23 - Mar 24
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. ...
Clean, little out dated but a great place to stay. Staff were so friendly. Perfect for if you are spending any time at the casino especially with the shuttle that runs.

Reviewed on Mar 16, 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 8 to Apr 9
$87 total
Apr 8 - Apr 9
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 ...
Yes the kitchen was a blessing

Reviewed on Mar 16, 2026

Opens in a new windowSleep Inn & Suites Winchester near University
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