Find a Hotel in Old Town Winchester

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Top hotels in Old Town Winchester

Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool

bluemont VA
This vacation home features an indoor pool and a gym. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
We have stayed here seven times now and will undoubtedly be back. Can’t beat this house!

Reviewed on Jan 11, 2026

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Opens in a new windowBreathtaking View with an Indoor Pool
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

3 out of 5
5 Caroline Drive Front Royal VA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $128 total per night from Feb 15 to Feb 16
$128 total
Feb 15 - Feb 16
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
Clean room, friendly and helpful staff, good breakfast, I would stay again.

Reviewed on Jan 16, 2026

Opens in a new windowTownePlace Suites by Marriott Front Royal
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
$98 nightly
The price is $107 total per night from Feb 15 to Feb 16
$107 total
Feb 15 - Feb 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 ...
The room was spotless , and the staff was very curtis

Reviewed on Feb 2, 2026

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 Feb 16 to Feb 17
$143 total
Feb 16 - Feb 17
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, ...
Clean nice room Great location for restaurants

Reviewed on Jan 28, 2026

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
$98 nightly
The price is $107 total per night from Feb 15 to Feb 16
$107 total
Feb 15 - Feb 16
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, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience.

Reviewed on Jan 31, 2026

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

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $92 total per night from Feb 14 to Feb 15
$92 total
Feb 14 - Feb 15
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. Free WiFi ...
The staff (phenomenal), the cleanliness, the attention to detail! The lady overseeing breakfast was a machine. Everything tidied up and perfect. The front desk staff were amazing!! Best staff we've ever seen and we travel a LOT!! 100% recommend staying here. It was less than a mile from the concert ...

Reviewed on Jan 18, 2026

Opens in a new windowQuality Inn Winchester
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

2.5 out of 5
1204 Berryville Avenue Winchester VA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $120 total per night from Feb 14 to Feb 15
$120 total
Feb 14 - Feb 15
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
The staff was wonderful!

Reviewed on Jan 30, 2026

Opens in a new windowHampton Inn Winchester N/Conference Center, VA
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 Feb 15 to Feb 16
$92 total
Feb 15 - Feb 16
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 ...
Room was very clean and spacious, staff was wonderful!

Reviewed on Jan 31, 2026

Opens in a new windowMicrotel Inn & Suites by Wyndham Winchester
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
$70 nightly
The price is $76 total per night from Feb 9 to Feb 10
$76 total
Feb 9 - Feb 10
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 ...
Room was good for the price, staff was friendly and helpful

Reviewed on Feb 4, 2026

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.

Recent Old Town Winchester hotel reviews by fellow wanderers

Spark by Hilton Winchester

Spark by Hilton Winchester

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"We love this hotel! We stay here often when traveling from the north to the south visiting family. It is impeccably clean and modern. The staff makes you feel welcome and the check-in is quick and efficient."
A verified traveler stayed at Spark by Hilton Winchester
Spark by Hilton Winchester

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