Winchester Vacations from $274

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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.
La Quinta Inn by Wyndham Indianapolis Airport Executive Dr

La Quinta Inn by Wyndham Indianapolis Airport Executive Dr

3 out of 5
Wayne
Price was $366, price is now $274 per person
$274
per person
Nov 13 - Nov 16
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Indianapolis (IND)
6.4/10 (981 reviews)
Clean place to stay, cheaper to buy on Expedia than at the front desk

Reviewed on Sep 24, 2025

Hampton Inn & Suites Indianapolis-Keystone

Hampton Inn & Suites Indianapolis-Keystone

2.5 out of 5
Save 100% on your flight
Price was $516, price is now $339 per person
$339
per person
Nov 13 - Nov 16
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Indianapolis (IND)
9.4/10 Exceptional! (958 reviews)
Excellent location and facilities. Rooms were spacious and comfortable.

Reviewed on Oct 4, 2025

Homewood Suites by Hilton Indianapolis-Keystone Crossing

Homewood Suites by Hilton Indianapolis-Keystone Crossing

3 out of 5
Save 100% on your flight
Price was $835, price is now $624 per person
$624
per person
Nov 18 - Nov 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Indianapolis (IND)
7.8/10 Good! (700 reviews)
We will be using this hotel for every trip to the state fair from now on.

Reviewed on Aug 20, 2025

Hilton Garden Inn Bloomington

Hilton Garden Inn Bloomington

3 out of 5
Downtown Bloomington
Save 100% on your flight
Price was $1,563, price is now $1,171 per person
$1,171
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Indianapolis (IND)
8.6/10 Excellent! (1,002 reviews)
It's a bit dated, but generally satisfactory hotel. No other comments.

Reviewed on Oct 5, 2025

Holiday Inn Express Hotel & Suites Indianapolis Dtn-Conv Ctr by IHG

Holiday Inn Express Hotel & Suites Indianapolis Dtn-Conv Ctr by IHG

3 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $820, price is now $641 per person
$641
per person
Nov 18 - Nov 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Indianapolis (IND)
9.2/10 Wonderful! (1,020 reviews)
Everything was great!

Reviewed on Oct 7, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winchester
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Discover the most popular places to visit in Winchester

Winchester Speedway

Catch an event at Winchester Speedway during your trip to Winchester.

Winchester Speedway

Winchester Golf Club

Enjoy a round of golf in Winchester at Winchester Golf Club.

Winchester Golf Club

Winchester Hotel Deals

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

Winchester
9.6/10 Exceptional! (180 reviews)
"House and backyard is huge! We absolutely enjoyed being outdoors with the kids, the indoor pool came in clutch while the weather was in the cooler side during our stay. Ted was readily available and provided clear communication."

Reviewed on Sep 24, 2025

Get rates
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Randolph Inn and Suites

Randolph Inn and Suites

2.5 out of 5
890 E Washington, Winchester, IN
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $121 total per night from Oct 12 to Oct 13
$121 total
Oct 12 - Oct 13
Total with taxes and fees
8.8/10 Excellent! (237 reviews)
"Great people working for our stay and was very friendly."

Reviewed on Sep 15, 2025

Randolph Inn and Suites
Days Inn by Wyndham Muncie -Ball State University

Days Inn by Wyndham Muncie -Ball State University

2 out of 5
3509 N Everbrook Ln, Muncie, IN
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $70 total per night from Nov 9 to Nov 10
$70 total
Nov 9 - Nov 10
Total with taxes and fees
6.6/10 (875 reviews)
"Room was clean and cool. Parking seemed safe and secure. Only issue I had was check in time. I arrived at 2 after a six hour drive. No rooms were available until the designated time of 3 which I found had to imagine."

Reviewed on Oct 6, 2025

Days Inn by Wyndham Muncie -Ball State University
See all 112 properties in Winchester
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.

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

How much does a Winchester vacation package cost?
You'll find cheap prices from $274 on Expedia for your Winchester getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
If you're hoping to book a cheap Winchester vacation package, consider traveling in June, July and November. You'll typically find better rates on flights and accommodations during these months — perfect for a budget-friendly getaway.
How many days is enough for Winchester?
Generally, a handful of days is enough to go to the top attractions during your Winchester vacation. But if you want to have time to kick back or go on day tours, consider extending your trip.
Is it worth booking a vacation package to Winchester?
It's no wonder a Winchester vacation is on the must-do list of many travelers. Top attractions like Winchester Speedway are just the beginning of things to keep you busy here.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester adventure underway.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can personalize your Winchester trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winchester?
If you have your Winchester travel dates locked in, book early to snap up some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Secure your perfect escape to Winchester with help from our Book Now, Pay Later vacations. There's no need to save up or wait for your next paycheck — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.