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
Price found within the past 48 hours. Click for updated prices.
Alhonna Resort LLC
Price was CA $1,079, price is now CA $837 per person
CA $837
per person
Jun 20 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to St. Louis (STL)
8.8/10 Excellent! (260 reviews)
Our first stay here was over 20 something years ago. It was older quaint and quiet. We have stayed at many other places from Tantara to Lodge of the 4 Seasons to Edgewater motel on the strip. But the AlHonna is always our go to.
Our recent stay was just as good as it always is but with bigger crowds now due the Ozark show.
They were almost done with major renovations, inside and out of all the buildings while we were there. Very nice improvements.
Hoping to come back again sometime this April.
Reviewed on Apr 3, 2026
The Wildwood Hotel
Price was CA $1,508, price is now CA $967 per person
CA $967
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,627 reviews)
The breakfaat was average, thou fresh. There was enough street parking nearby, safe.
Reviewed on Mar 30, 2026
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
Grand Center
Price was CA $1,653, price is now CA $1,302 per person
CA $1,302
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to St. Louis (STL)
8.8/10 Excellent! (1,065 reviews)
Everything was great! Hotel is beautiful, staff was so friendly, perfect trip!
Reviewed on Apr 6, 2026
The Royal Sonesta Chase Park Plaza St. Louis
Central West End
Price was CA $1,593, price is now CA $1,266 per person
CA $1,266
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to St. Louis (STL)
9/10 Wonderful! (1,005 reviews)
Beautiful hotel - three phenomenal restaurants. Perfect location. We absolutely love The Chase Park Plaza.
Reviewed on Apr 6, 2026
The Knight Center at Washington University
Price was CA $1,242, price is now CA $992 per person
CA $992
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.4/10 Exceptional! (505 reviews)
It's an excellent property if on campus visit is the major purpose
Reviewed on Apr 7, 2026
Winchester Hotel Deals
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Apr 19 to Apr 20
CA $139
CA $162 total
Apr 19 - Apr 20
includes taxes & fees
8.8/10 Excellent! (3,147 reviews)
The room was very clean, there was always someone at the front desk and each staff member I encountered was friendly. The breakfast buffet was a nice bonus. Overall 10/10.
Reviewed on Apr 6, 2026
Drury Plaza Hotel St. Louis at the Arch
2 South 4th Street St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $250 per night from Apr 8 to Apr 9
CA $250
CA $293 total
Apr 8 - Apr 9
includes taxes & fees
Pear Tree Inn St. Louis Near Union Station
2211 Market Street St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Apr 13 to Apr 14
CA $174
CA $203 total
Apr 13 - Apr 14
includes taxes & fees
8.8/10 Excellent! (1,933 reviews)
My kids appreciated the pool (crowded as it was!). The happy hour and fountain soda in the breakfast area was a pleasant surprise. Rooms are a bit worn, hallway looked like it had some water issues as well with missing tiles/exposed pipes. Bed was too soft for me. We had to switch rooms due to wet ...
Reviewed on Apr 6, 2026
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.
Discover the most popular places to visit in Winchester
Busch Stadium
5/5(19 reviews)
Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music or attend a baseball game.
Gateway Arch
4.5/5(37 reviews)
Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.
St. Louis Zoo
4.5/5(7 reviews)
In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.
What to do in Winchester
St. Louis Ghost Tour: Sinister Sins & Shadows
CA $33
per adult
Lemp Haunted Neighborhood Walking Tour
CA $41
per adult
84% of travellers recommend
St Louis Self-Guided Driving and Walking Audio Tour
CA $21
per traveller
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
