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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 refundable
$100 nightly
The price is $112 total per night from Nov 29 to Nov 30
$112 total
Nov 29 - Nov 30
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 ...
"Very nice"

Reviewed on Nov 1, 2026

Opens in a new windowComfort Inn & Suites 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
$104 nightly
The price is $115 total per night from Nov 8 to Nov 9
$115 total
Nov 8 - Nov 9
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 ...
"Arrived late. Staff member at desk very friendly and welcoming. Morning staff very friendly. Room spacious liked the floor plan"

Reviewed on Nov 3, 2026

Opens in a new windowLa Quinta 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 $77 total per night from Dec 1 to Dec 2
$77 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 ...
"Je remarque que lorsque nous réservons avez Expedia nous avons des chambres médiocres. La salle de bain excessivement petite et très salle. Je ne retournerai plus à cet endroit et je ne réserverai plus avec Expedia"

Reviewed on Nov 3, 2026

Opens in a new windowTravelodge by Wyndham Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $84 total per night from Nov 10 to Nov 11
$84 total
Nov 10 - Nov 11
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests ...
"We always like to stay at the hotel if we are needing a stay in that area. It is always very good and the onsite restaurant is excellent"

Reviewed on Nov 3, 2026

Opens in a new windowRamada by Wyndham Strasburg/Shenandoah Valley
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
$130 nightly
The price is $148 total per night from Nov 19 to Nov 20
$148 total
Nov 19 - Nov 20
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, ...
Opens in a new windowThe George Washington Hotel, A Wyndham Grand Hotel
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 $92 total per night from Nov 8 to Nov 9
$92 total
Nov 8 - Nov 9
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like full ...
Opens in a new windowMicrotel Inn & Suites by Wyndham Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Nov 15 to Nov 16
$90 total
Nov 15 - Nov 16
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 ...
Opens in a new windowTRU By Hilton Winchester
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
Fully refundable
$78 nightly
The price is $86 total per night from Nov 22 to Nov 23
$86 total
Nov 22 - Nov 23
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 ...
Opens in a new windowQuality Inn Winchester
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
$86 nightly
The price is $95 total per night from Nov 29 to Nov 30
$95 total
Nov 29 - Nov 30
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 ...
Opens in a new windowCountry Inn & Suites by Radisson, Winchester, VA
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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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