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Featured Winchester Family Hotels

Country Inn & Suites by Radisson, Winchester, VA

141 Kernstown Commons Blvd Winchester VA

Fully refundable

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 ...

Fairfield Inn & Suites Strasburg Shenandoah Valley

33760 Old Valley Pike Strasburg VA

Fully refundableReserve now, pay when you stay

Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

Fully refundableReserve now, pay when you stay

Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...

Hampton Inn Front Royal

9800 Winchester Rd Front Royal VA

Fully refundableReserve now, pay when you stay

Book a stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

Red Roof Inn Winchester, VA

991 Millwood Pike Winchester VA

Fully refundableReserve now, pay when you stay

Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Fully refundableReserve now, pay when you stay

Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

Fully refundableReserve now, pay when you stay

Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...

Holiday Inn Express Winchester South-Stephens City by IHG

165 Town Run Ln Stephens City VA

Fully refundable

Book a stay at this business-friendly hotel in Stephens City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

Quality Inn Stephens City - Winchester South

167 Town Run Ln Stephens City VA

Fully refundableReserve now, pay when you stay

Book a stay at this business-friendly hotel in Stephens City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

Hotel Strasburg

213 S. Holliday Street Strasburg VA

Book a stay at this historic hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Strasburg Museum and Hupp's Hill Civil ...

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East Winchester VA

Fully refundableReserve now, pay when you stay

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 ...

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

Fully refundableReserve now, pay when you stay

Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...

See all 2,041 properties in Winchester

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.

Hotels with Pools in Winchester

Country Inn & Suites by Radisson, Winchester, VA

141 Kernstown Commons Blvd Winchester VA

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 ...

8.6/10 Excellent! (1,007 reviews)

Room was ok….toilet seat loose. No cold water. Just lukewarm.

Reviewed on Jan 5, 2026

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...

9.2/10 Wonderful! (1,004 reviews)

Clean rooms, nice water pressure and never ending hot water ! Only improvements I would suggest is for holiday stays like new years that has a bar maybe make it for adults who want to enjoy the music and not filled with kids and those boys t

Reviewed on Jan 2, 2026

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...

8.8/10 Excellent! (1,005 reviews)

if you are looking for a spotlessly, clean and new hotel with an extremely comfortable bed and soft pillows this is the place for you. this hotel is conveniently located for a quick stop off of the highway and not far from downtown old Winchester, which is beautiful. The bathroom was new modern and ...

Reviewed on Jan 5, 2026

See all 2,041 properties in Winchester

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.

Hotels With Connecting Rooms in Winchester

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...