Winchester Vacations from $456
Book a Hotel + Flight or Car together to unlock savings
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.
Hampton Inn Indianapolis Downtown Across from Circle Centre
Downtown Indianapolis
Price was $583, price is now $456 per person
$456
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
New York (LGA) to Indianapolis (IND)
8.8/10 Excellent! (1,009 reviews)
It was a short walk to gainbridge. Parking overnight in valet was expensive.
Reviewed on May 27, 2026
Omni Severin Hotel
Downtown Indianapolis
Price was $634, price is now $499 per person
$499
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
New York (LGA) to Indianapolis (IND)
9.4/10 Exceptional! (1,018 reviews)
Staff were ok at check in but didn’t tell us about the pool etc
Reviewed on Jun 3, 2026
Hyatt House Indianapolis Downtown
Downtown Indianapolis
Price was $768, price is now $609 per person
$609
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
New York (LGA) to Indianapolis (IND)
9/10 Wonderful! (1,201 reviews)
Great location, everything was perfect. Great free breakfast in am
Reviewed on May 29, 2026
Hyatt Place Indianapolis Downtown
Downtown Indianapolis
Price was $751, price is now $596 per person
$596
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
New York (LGA) to Indianapolis (IND)
9/10 Wonderful! (1,490 reviews)
The staff was very nice. The hotel was very clean. Would’ve liked to have been told that there was no view at all, besides an air-conditioning unit outside my window. Order dinner from the restaurant bar grilled chicken sandwich was burnt an edible hamburger bun was completely burnt. Breakfast was not very good.
Reviewed on Jun 1, 2026
The Alexander, Autograph Collection
Downtown Indianapolis
Price was $755, price is now $600 per person
$600
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
New York (LGA) to Indianapolis (IND)
8.8/10 Excellent! (1,002 reviews)
Right in the perfect location to quickly go eat or shop. Room was immaculate. Beautifully decorated. Even had a hand held steamer for your wrinkled clothes. We will 100% stay at this wonderful hotel again!
Reviewed on May 29, 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 Jun 5 to Jun 6
$121 total
Jun 5 - Jun 6
Total with taxes and fees
9/10 Wonderful! (258 reviews)
"The rooms (although we had a small pet) had never been updated. They were extremely old, the lot was not well lit, and we were separate from the main building. It smelled, the a/c barely worked, the beds were tiny and hard. I would never recommend."
Reviewed on May 18, 2026
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
Comfort Suites Richmond East
421 Commerce Road Richmond IN
Fully refundable
$99 nightly
The price is $111 total per night from Jun 28 to Jun 29
$111 total
Jun 28 - Jun 29
Total with taxes and fees
9.4/10 Exceptional! (760 reviews)
"The hotel was clean and well-maintained. Staff with who we interacted were friendly and professional. Good location off of Rt 40 at I-70. The hotel had a nice breakfast in the morning, but no regular coffee!!"
Reviewed on Jun 1, 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.