
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.

Sleep Inn Indianapolis East
Price was CA $697, price is now CA $648 per person
CA $648
per person
May 4 - May 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Indianapolis (IND)
8/10 Very Good! (1,473 reviews)
The room was clean, that was the only good thing. The television didn’t work, there was no running water to take a shower and the phone didn’t work so I couldn’t call the desk. I went to the desk at 9 & 10 pm to talk to someone but there no one there snd no way to contact anyone. The next morning I tried to explain to a hotel worker what had happened and he said that there is always someone at the desk and became very rude so I just left. I will never use your site again
Reviewed on Jan 25, 2026

The Landing Apartments Indianapolis
Price was CA $1,128, price is now CA $1,013 per person
CA $1,013
per person
May 4 - May 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 $1,095, price is now CA $990 per person
CA $990
per person
May 4 - May 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 North
College Park
Price was CA $829, price is now CA $772 per person
CA $772
per person
May 4 - May 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Indianapolis (IND)
7.8/10 Good! (1,000 reviews)
Room was great, staff was super friendly. Pool was down for repairs, which was a disappointment. Breakfast was delicious, especially the made to order omelette.
Reviewed on Feb 1, 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 (899 reviews)
The room was a great deal and worth the price. It was nothing fancy, but the room was clean and the space seemed to be well-maintained.
Reviewed on Jan 19, 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.







