Cottages in Winchester

Free cancellation options if plans change

Unlock travel rewards with One Key

Save more with Member Prices

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages 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.

Top neighborhoods in Winchester

Old Town Winchester

Winchester's Old Town Winchester neighborhood is known for its restaurants and bars, and entices visitors with attractions including Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester Historic District

Winchester's Winchester Historic District neighborhood is home to attractions such as Bright Box Theater and Winchester Little Theater.

Top landmarks in Winchester

Winchester and related destinations

Wander through America's oldest pedestrian mall, where historic buildings house quirky shops and restaurants that locals fiercely defend as the valley's best. The Museum of the Shenandoah Valley tells stories through art and gardens that change dramatically with the seasons. Civil War buffs can explore Stonewall Jackson's Headquarters, where the general's personal items remain eerily untouched. Patsy Cline's modest historic house offers an intimate glimpse into the country legend's early life before Nashville fame. After dark, Bright Box Theater fills with laughter and live music in a space that feels both sophisticated and warmly familiar. Kids can touch everything at the hands-on Shenandoah Valley Discovery Museum, a welcome relief for parents tired of saying 'don't touch that.'

Find out more about Winchester

Visitors to Winchester like this family-friendly city's historical sites, restaurants, and skyscrapers. Learn about the local heritage of Winchester at landmarks like Patsy Cline Historic House and Stonewall Jackson's Headquarters. There's plenty more to see, including sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

Keep exploring