
Winchester Vacation Packages
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Your Winchester Vacation
History, cuisine, art and more … There's so much to experience with a Winchester vacation package. And with the ability to customize your city getaway, you know it'll be one that's tough to forget. Want to explore? Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana are among the leading places to visit during your trip to Winchester. Expedia has what you need to escape your routine. Tailor your vacation to Winchester to suit your style of travel, whatever that may look like.
Top Winchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.

The Landing Apartments Indianapolis
Price was CA $1,781, price is now CA $1,353 per person
CA $1,353
per person
Apr 26 - May 3
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Indianapolis (IND)
9/10 Wonderful! (36 reviews)
Highly recommended stay, I stayed for 1 month long for school safe quiet and clean. Full laundry room inside room very convenient large apartments. Communication with management was great. There are no elevators and I was on the 3rd floor but I am active does not bother me. Just keep that in mind if you cant climb stairs. Great place ! High recommended!
Reviewed on Nov 24, 2025

Bottleworks Hotel
Downtown Indianapolis
Price was CA $2,379, price is now CA $1,683 per person
CA $1,683
per person
Apr 26 - May 3
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Indianapolis (IND)
9.8/10 Exceptional! (1,664 reviews)
Everything and everyone was absolutely wonderful!
Reviewed on Feb 6, 2026

Embassy Suites by Hilton Indianapolis Downtown
Downtown Indianapolis
Price was CA $2,037, price is now CA $1,546 per person
CA $1,546
per person
Apr 26 - May 3
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Indianapolis (IND)
8.4/10 Very Good! (1,003 reviews)
Great location! The complimentary breakfast is a must with good choices in breakfast meats, omelettes, breads, yogurts, and cereals.
Reviewed on Jan 26, 2026

Ironworks Hotel Indy
Price was CA $2,269, price is now CA $1,777 per person
CA $1,777
per person
Apr 26 - May 3
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Indianapolis (IND)
9.8/10 Exceptional! (1,698 reviews)
Great staff, great room and great food within the hotel! Amazing and will be back!
Reviewed on Feb 6, 2026

The Alexander
Downtown Indianapolis
Price was CA $2,393, price is now CA $1,882 per person
CA $1,882
per person
Apr 26 - May 3
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Indianapolis (IND)
8.8/10 Excellent! (1,000 reviews)
The newly renovated rooms were clean and have a trendy design. The valet was super helpful and prompt even in the snowy cold weather. The greeting at check in and out was upbeat and they went out of their way to explain the processes and expectations. I also appreciated that I was asked by the reception what the hotel could have added to the room to make it a better stay for everyone as they continue to update the rooms. Which for me was extra charging ports on the night stand tables and more direction on guest wifi set up. This hotel is in a fun food area and right next to the Colts Stadium. I didn't get to try the food because I arrived later at night, but the menu selection sounded delicious. Price for the overnight experience was on point.
Reviewed on Jan 30, 2026
Winchester Hotel Deals

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Winchester IN
9.6/10 Exceptional! (184 reviews)
This was a beautiful home was enjoyed by all. The amenities are great, Walmart is right around the corner, the pool was warm and Ted was very welcoming. We were disappointed to learn that the hot tub had been closed early due to cold weather, but that don’t stop us from having a great time! We would ...
Reviewed on Dec 16, 2025

Randolph Inn and Suites
890 E Washington Winchester IN
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (250 reviews)
Yes, the room was very clean and the staff was extremely helpful
Reviewed on Jan 21, 2026

Days Inn by Wyndham Muncie -Ball State University
3509 N Everbrook Ln Muncie IN
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Feb 8 to Feb 9
CA $92
CA $103 total
Feb 8 - Feb 9
includes taxes & fees
6.8/10 (902 reviews)
Nice enough very quick check in clean
Reviewed on Feb 5, 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.







