
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.


Omni Severin Hotel
Downtown Indianapolis
Price was CA $1,198, price is now CA $1,020 per person
CA $1,020
per person
Aug 27 - Aug 31
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
9.4/10 Exceptional! (1,098 reviews)
My wife and I had a suite which was very large, but the bathroom was extremely small. Good shower, but the rest of the bathroom was very cramped with only room for one shaving kit. No room for another person’s toiletries. There was a dedicated bedroom and a dedicated sitting area, but no divider between the two. You couldn’t watch tv without waking the other person up. The bed was comfortable. The room just had a lot of wasted space that could have been better utilized.
I ordered room service one evening, but after 1 hour I called because it hadn’t arrived. It was 11:00pm by this time. She said they were very busy and it would be another 10 min. I told her to cancel it because I was going to bed and would not accept it. 20 min later I had to get out of bed and answer the door because they were delivering it. I told her to keep it because I had cancelled it and did not want to be charged for it. Fortunately, it was not on my bill when checking out.
We also had a problem with housekeeping. The second day they did not show up and I had to find the lady at 8:00pm to ask her to clean it. We hadn’t been in the room all day. The next 2 days she didn’t clean until after 6:00pm even though we had also been out both of those days.
There is currently a lot of major road work going on around the hotel. That is not the hotel’s fault, but it has caused the closure of the shopping mall next to it.
Bottom line- it’s a 3 1/2 star facility but not paying attention to details made it less.
Reviewed on Jun 30, 2026

Landing Furnished Apartments Near Northside
Near Northside
Price was CA $1,466, price is now CA $1,249 per person
CA $1,249
per person
Sep 13 - Sep 19
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
9.6/10 Exceptional! (5 reviews)
Beautiful clean place very spacious for the wife and I and would be interested in it again for the wife and I with grandkids
Reviewed on Jun 10, 2026

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel
Downtown Indianapolis
Price was CA $1,105, price is now CA $957 per person
CA $957
per person
Aug 27 - Aug 31
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
9.2/10 Wonderful! (393 reviews)
While we found the staff to be friendly and helpful, the problem with the hotel is the location. It is right next to the bus station, and on a busy street (S. Delaware) that has LOUD cars and motorcycles racing by at all hours of the night. In addition, there is a lot of homeless people around the building. There is an abandoned building across the street on E. Washington and a number of homeless hang out there. We also saw a guy on drugs bent over and just standing there in a daze. I realize that the hotel can't do much about it, but I wouldn't stay there again. Rooms were also very cramped.
Reviewed on Jun 24, 2026

Baymont by Wyndham Plainfield/ Indianapolis Arpt Area
Price was CA $1,013, price is now CA $909 per person
CA $909
per person
Sep 13 - Sep 19
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Indianapolis (IND)
8.4/10 Very good! (1,403 reviews)
No bad at all, just the room we stay the bathroom need maintenance like the faucet was loose, need to be re caulking ,paint… overall was clean, room 301
Reviewed on Jul 2, 2026
Winchester Hotel Deals

Randolph Inn and Suites
890 E Washington Winchester IN
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Jul 4 to Jul 5
CA $138
CA $154 total
Jul 4 - Jul 5
includes taxes & fees
9/10 Wonderful! (261 reviews)
"Clean, quiet, very friendly staff"
Reviewed on Jun 28, 2026

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Winchester IN
9.8/10 Exceptional! (205 reviews)
"This was a great property for our large family group… ages 1-88… the dining table is huge and we had plenty of room for dinner, as well as board games and puzzles. We used the volleyball and badminton nets, as well as the hot tub and pool. Unfortunately, it was too hot for a bonfire, but we will ..."
Reviewed on Jul 2, 2026

Baymont by Wyndham Richmond I-70
912 Mendleson Dr Richmond IN
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Jul 5 to Jul 6
CA $95
CA $107 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"The hotel was definitely older and in need of repairs."
Reviewed on Jul 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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