Winchester Vacation Packages
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Top Winchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
Grand Center
Price was CA $1,076, price is now CA $889 per person
CA $889
per person
Jun 12 - Jun 15
found 17 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.8/10 Excellent! (1,049 reviews)
Everything was great! Hotel is beautiful, staff was so friendly, perfect trip!
Reviewed on Apr 6, 2026
The Wildwood Hotel
Price was CA $1,473, price is now CA $931 per person
CA $931
per person
Jun 12 - Jun 15
found 17 hours ago
Roundtrip non-stop flight included
Calgary (YYC) 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
The Cheshire
Price was CA $1,196, price is now CA $958 per person
CA $958
per person
Jun 12 - Jun 15
found 17 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.6/10 Excellent! (1,011 reviews)
It had unique decor which was fun. Staff was nice But the lights were broken and there was a leftover can under a chair
Reviewed on Apr 1, 2026
The Royal Sonesta Chase Park Plaza St. Louis
Central West End
Price was CA $1,247, price is now CA $1,000 per person
CA $1,000
per person
Jun 12 - Jun 15
found 17 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9/10 Wonderful! (1,008 reviews)
Beautiful hotel - three phenomenal restaurants. Perfect location. We absolutely love The Chase Park Plaza.
Reviewed on Apr 6, 2026
Hollywood Casino & Hotel St. Louis
Price was CA $1,342, price is now CA $1,093 per person
CA $1,093
per person
Jun 12 - Jun 15
found 17 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.4/10 Very Good! (2,194 reviews)
The room was clean, fresh, modern and excellent. Check in worked well and promptly. It was a great experience
Reviewed on Apr 9, 2026
Winchester Hotel Deals
Sleep Inn & Suites South Jacksonville
2401 Holliday Ln Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Apr 19 to Apr 20
CA $119
CA $133 total
Apr 19 - Apr 20
includes taxes & fees
9.4/10 Exceptional! (657 reviews)
Yes to both
Reviewed on Apr 3, 2026
Best Western Jacksonville Inn
1709 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Apr 12 to Apr 13
CA $104
CA $118 total
Apr 12 - Apr 13
includes taxes & fees
8.4/10 Very Good! (766 reviews)
Staff is great as usual .. been staying here for about 2 months now for work. Always clean and comfy
Reviewed on Apr 2, 2026
Quality Inn Jacksonville near I-72
200 Comfort Drive Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Apr 23 to Apr 24
CA $98
CA $109 total
Apr 23 - Apr 24
includes taxes & fees
7.8/10 Good! (456 reviews)
Not the best not the worst
Reviewed on Apr 2, 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.
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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.
