Winchester Vacation Packages
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Top Winchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield
Price was CA $2,147, price is now CA $1,557 per person
CA $1,557
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.2/10 Very Good! (779 reviews)
Staff was informative during check-in. Room was clean and the TV even had WELCOME with my name on it. Would stay here again.
Reviewed on Dec 22, 2025
The Cheshire
Price was CA $1,993, price is now CA $1,527 per person
CA $1,527
per person
Mar 19 - Mar 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.6/10 Excellent! (1,002 reviews)
I love the whole "English Tudor" vibe at the hotel. The room was clean and well-appointed. The staff is friendly and the hotel lounge is a fun place to unwind.
Reviewed on Feb 6, 2026
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
Grand Center
Price was CA $2,048, price is now CA $1,605 per person
CA $1,605
per person
Mar 19 - Mar 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.8/10 Excellent! (1,022 reviews)
It was good and beautiful on the inside. Loved all the art. The bed was comfy and the room was like an apartment .The only thing that stunk is that there wasn't a microwave in the room. But there was one on the floor so it worked out.
Reviewed on Feb 3, 2026
Winchester Hotel Deals
Best Western Jacksonville Inn
1709 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from Feb 8 to Feb 9
CA $96
CA $109 total
Feb 8 - Feb 9
includes taxes & fees
8.4/10 Very Good! (753 reviews)
Check-in was easy! No hassles! Room is clean and the TV works😊
Reviewed on Jan 7, 2026
Sleep Inn & Suites South Jacksonville
2401 Holliday Ln Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Feb 15 to Feb 16
CA $110
CA $122 total
Feb 15 - Feb 16
includes taxes & fees
9.2/10 Wonderful! (633 reviews)
Clean, quiet and comfortable. Have stayed many times and will continue.
Reviewed on Jan 25, 2026
Hampton Inn Jacksonville
1725 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Feb 13 to Feb 14
CA $111
CA $127 total
Feb 13 - Feb 14
includes taxes & fees
8.8/10 Excellent! (503 reviews)
Clean room. Great friendly staff.
Reviewed on Jan 17, 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.
