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.
Candlewood Suites Indianapolis Northwest by IHG
Price was CA $1,567, price is now CA $1,135 per person
CA $1,135
per person
Jul 4 - Jul 11
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Indianapolis (IND)
8/10 Very Good! (387 reviews)
They are in the middle of renovations, so things weren't in the best condition, but the rooms were spacious and had all the amenities that we needed.
Reviewed on Apr 8, 2026
Holiday Inn Express Hotel & Suites Greenwood by IHG
Price was CA $1,650, price is now CA $1,271 per person
CA $1,271
per person
Jul 4 - Jul 11
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Indianapolis (IND)
9/10 Wonderful! (1,013 reviews)
Clean, modern, exactly as expected. Good quality place for the price.
Reviewed on May 11, 2026
The Alexander
Downtown Indianapolis
Price was CA $2,061, price is now CA $1,619 per person
CA $1,619
per person
Jul 4 - Jul 11
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Indianapolis (IND)
8.8/10 Excellent! (1,003 reviews)
Very clean. Staff were excellent! Very nice place to stay. Would definitely stay here again. Walking distance to some good eateries as well as Lucas Oil Stadium.
Reviewed on May 10, 2026
Marriott Indianapolis Downtown
Downtown Indianapolis
Price was CA $2,172, price is now CA $1,771 per person
CA $1,771
per person
Jul 4 - Jul 11
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Indianapolis (IND)
9.2/10 Wonderful! (1,016 reviews)
Everything was great. No issues. Had a great time in Indianapolis.
Reviewed on May 11, 2026
Embassy Suites by Hilton Indianapolis North
College Park
Price was CA $1,892, price is now CA $1,576 per person
CA $1,576
per person
Jul 4 - Jul 11
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Indianapolis (IND)
8/10 Very Good! (1,002 reviews)
this is our favorite place to stay in Indy! always clean, staff is kind and breakfast is delicious!!
Reviewed on May 12, 2026
Winchester Hotel Deals
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Winchester IN
9.8/10 Exceptional! (200 reviews)
We have rented large reunion places before. This one looks better online than it was in person. Functionally everything worked, but the decor and furniture were highly dated, hence four stars instead of five. The cleanliness was OK except in the basement, which was very dusty. We had great conversations ...
Reviewed on Mar 8, 2026
Randolph Inn and Suites
890 E Washington Winchester IN
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from May 26 to May 27
CA $133
CA $149 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (256 reviews)
Room was clean and ready upon arrival. Front staff outstanding!
Reviewed on Apr 25, 2026
Baymont by Wyndham Richmond I-70
912 Mendleson Dr Richmond IN
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from May 17 to May 18
CA $99
CA $110 total
May 17 - May 18
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
Decent hotel, little dated rooms but convenient location. Pool area looked nice, but didn't use. Shower was good, bed was hard.
Reviewed on May 13, 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.
