Winchester Vacation Packages
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Your Winchester Vacation
When a fun city break is calling, answer it with a Winchester vacation package. The neighborhood of Maplewood, which is great for bars and pubs, gift and craft shops and dining, makes a terrific base for your adventures. There's plenty to include on your itinerary during your trip to Winchester, starting with top attractions such as Castlewood State Park and American Kennel Club Museum of the Dog. Your Winchester vacation is just clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored just for you.
Top Winchester Vacation Deals
The Wildwood Hotel
Reviewed on Feb 19, 2026
Winchester Hotel Deals
21C Museum Hotel St Louis
The one of the best hotels in stl
Reviewed on Feb 21, 2026
Pear Tree Inn St. Louis Airport
Always great and very friendly
Reviewed on Feb 21, 2026
Clayton Plaza Hotel & Extended Stay
Good
Reviewed on Feb 20, 2026
Discover the most popular places to visit in Winchester
Busch Stadium
Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's fascinating museums or attend a baseball game.
Gateway Arch
Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.
Enterprise Center
Catch an event at Enterprise Center during your trip to St. Louis. Experience the area's fascinating museums or attend a baseball game.
What to do in Winchester
St. Louis Ghost Tour: Sinister Sins & Shadows
Lemp Haunted Neighborhood Walking Tour
