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Hotels near Old Town Winchester
SpringHill Suites by Marriott Winchester
280 MARKET STREET, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Sep 28 to Sep 29
CA $161
CA $176 total
Sep 28 - Sep 29
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
"Pleasant"
Reviewed on Sep 22, 2025
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Oct 26 to Oct 27
CA $138
CA $150 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Great Accommodations
"No complaints, everything was perfect. Had an enjoyable overnight stay. We had a Saturday morning breakfast which was served between seven and 10. We arrived at nine. Rather slim pickings. Had one young lady trying to keep up with the inventory. She did her best."
Reviewed on Sep 21, 2025
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Oct 2 to Oct 3
CA $176
CA $199 total
Oct 2 - Oct 3
includes taxes & fees
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
"The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool ..."
Reviewed on Sep 24, 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Sep 28 to Sep 29
CA $151
CA $164 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
"The room was very well laid out. Beds were comfortable. Breakfast was standard fare but tasty. The serving staff were very efficient. We were pleasanty surprised with our first visit hetr. It is an ideal layover point when travelling onward to Shenandoah National Park"
Reviewed on Sep 22, 2025
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Oct 26 to Oct 27
CA $117
CA $127 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
"Very nice place to stay. Everything is perfectly placed and the amenities were good."
Reviewed on Sep 21, 2025
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is CA $129 per night from Oct 26 to Oct 27
CA $129
CA $145 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
"It was a nice 1/2 stop for us"
Reviewed on Sep 19, 2025
Courtyard by Marriott Winchester
300 Marriott Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Oct 2 to Oct 3
CA $149
CA $162 total
Oct 2 - Oct 3
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
"Very clean and the employees hospitality was outstanding."
Reviewed on Sep 15, 2025
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd, Winchester, VA
Fully refundable
The price is CA $126 per night from Oct 26 to Oct 27
CA $126
CA $138 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
"Helpful staff."
Reviewed on Sep 23, 2025
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Oct 5 to Oct 6
CA $105
CA $117 total
Oct 5 - Oct 6
includes taxes & fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
"Room was very clean and comfortable. Breakfast was basic but better than most I've been to recently. Very satisfied with the stay."
Reviewed on Sep 22, 2025
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Recent Old Town Winchester hotel reviews by fellow wanderers
The George Washington Hotel, A Wyndham Grand Hotel
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool is a spectacle to behold! The beauty along with the perfect water temperature provided a perfect ending to our evening!"
A verified traveller stayed at The George Washington Hotel, A Wyndham Grand Hotel
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