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
$99 nightly
The price is $108 total per night from Dec 15 to Dec 16
$108 total
Dec 15 - Dec 16
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 ...
Wonderfully clean! Staff was friendly and breakfast was great! Truck noise from highway is loud, but I fell asleep immediately because of the cleanliness and high quality, comfy bedding!

Reviewed on Dec 3, 2025

Opens in a new windowComfort Inn & Suites Winchester
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
$101 nightly
The price is $110 total per night from Dec 28 to Dec 29
$110 total
Dec 28 - Dec 29
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 ...
Clean room & the staff.

Reviewed on Nov 30, 2025

Opens in a new windowSpringHill Suites by Marriott 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 Dec 7 to Dec 8
$144 total
Dec 7 - Dec 8
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, ...
The breakfast was very good. The menu had a lot of options. It came to our table nice and hot! I loved the waffle with Lemon ricotta, syrup and butter. Our waitress always knew when to fill my coffee to keep it warm! Everything was very clean and neatly set up. The waitresses were also cheerful and ...

Reviewed on Nov 20, 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
$95 nightly
The price is $104 total per night from Dec 14 to Dec 15
$104 total
Dec 14 - Dec 15
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 ...
Everything was clean. Smelt good. Staff was very friendly!

Reviewed on Dec 3, 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
$73 nightly
The price is $79 total per night from Dec 14 to Dec 15
$79 total
Dec 14 - Dec 15
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 ...
Just a quick overnight - very impressed with the cleanliness, quietness and friendly staff! I was too slow moving to take advantage of the breakfast! I would definitely stay here again!

Reviewed on Dec 2, 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
$99 nightly
The price is $112 total per night from Jan 4 to Jan 5
$112 total
Jan 4 - Jan 5, 2026
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 ...
Room was quiet and comfy and staff were friendly! Entry way was decorated for the holidays!

Reviewed on Dec 1, 2025

Opens in a new windowHampton Inn Winchester-University/Mall Area
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd Front Royal VA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $119 total per night from Dec 11 to Dec 12
$119 total
Dec 11 - Dec 12
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 ...
Room was spotless, place was quiet and our welcome at the desk was perfect

Reviewed on Dec 1, 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
$81 nightly
The price is $88 total per night from Jan 4 to Jan 5
$88 total
Jan 4 - Jan 5, 2026
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 ...
Average room, very clean. Breakfast was disappointing.

Reviewed on Dec 2, 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 7 to Dec 8
$74 total
Dec 7 - Dec 8
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 ...
Was congratulating myself on having chosen a nice, clean, simple place charging only $15 fee for each of my pets. Nice layout, smooth check in, pleasant staff. Until my better half pointed out the animal feces, dried and obviously a long-term resident, next to the bedside chair. Ed always leave tips ...

Reviewed on Nov 27, 2025

Opens in a new windowTravelodge by Wyndham Winchester
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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.

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