Winchester Vacations from $178
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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.
The Latest Winchester vacation packages
Price found within the past 48 hours. Click for updated prices.
Omni Severin Hotel
Downtown Indianapolis
Price was $368, price is now $289 per person
$289
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9.4/10 Exceptional! (1,118 reviews)
We had an awesome stay at this hotel! Clean rooms that are very well cared for by the excellent housekeeping staff. The only problem was that one of the elevators was out of service so it took a few extra minutes to get up to our room. We were there to watch the Indiana Fever games as were many of the guests! We had a ball and really appreciate the hospitality!
Reviewed on Jul 20, 2026
Hotel Indy, Indianapolis, a Tribute Portfolio Hotel
Downtown Indianapolis
Price was $348, price is now $273 per person
$273
per person
Oct 2 - Oct 4
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9.2/10 Wonderful! (394 reviews)
I liked that it was close walking distance to the Fieldhouse for the Fever game. The staff was nice and friendly. The room was nice and clean all in all. It was a good overnight stay except… Our room the air conditioner was not working. It was 80° sleeping and I felt like we were at the races from the outside traffic speeding up and down the road other than that, it was a nice place.
Reviewed on Jul 19, 2026
JW Marriott Indianapolis
Downtown Indianapolis
Price was $377, price is now $307 per person
$307
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9.4/10 Exceptional! (1,352 reviews)
Enjoyed my stay there. However, I thought it was ridiculous to charge $14 a day for internet. The food at Dean's seafood and steak was pricey and not that good. But overall very good hotel. No free breakfast.
Reviewed on Jul 20, 2026
Stay near popular Winchester attractions
Winchester Hotel Deals
Randolph Inn and Suites
890 E Washington Winchester IN
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $121 total per night from Jul 21 to Jul 22
$121 total
Jul 21 - Jul 22
Total with taxes and fees
9/10 Wonderful! (266 reviews)
"We liked the room and property. The only things that came to mind were, the bars of soap are very tiny and maybe start using 1 cup Keurig maker in the rooms instead of the small coffee pods."
Reviewed on Jul 19, 2026
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Winchester IN
9.8/10 Exceptional! (208 reviews)
"This home was perfect for what we needed. There was plenty of space for our extended family of 28. The indoor pool was larger than I expected based on pictures, so it was great for keeping the kids busy. There was plenty of yard space for the kids to run and play games. There was a large table that ..."
Reviewed on Jul 15, 2026
Baymont by Wyndham Richmond I-70
912 Mendleson Dr Richmond IN
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $83 total per night from Aug 2 to Aug 3
$83 total
Aug 2 - Aug 3
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"I've stayed here several times always clean and the staff is beyond great nice and respectful the cook Richard is always nice and cares breakfast is good Alot to choose from"
Reviewed on Jul 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.
Find the Best Winchester Vacation Packages
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 4,800 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
