Winchester Vacations from $264

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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.
Holiday Inn Indianapolis Airport by IHG

Holiday Inn Indianapolis Airport by IHG

3 out of 5
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9.2/10 Wonderful! (1,002 reviews)
Always a great stay. Only hotel I use to fly out of IND. shuttle always on time.

Reviewed on Jul 14, 2025

Fairfield Inn & Suites by Marriott Indianapolis Carmel

Fairfield Inn & Suites by Marriott Indianapolis Carmel

2.5 out of 5
per person
Sep 7 - Sep 10
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Indianapolis (IND)
9.6/10 Exceptional! (536 reviews)
The best thing about this property is having Joseph at the front desk and whenever you need him!

Reviewed on Jul 13, 2025

Omni Severin Hotel

Omni Severin Hotel

4 out of 5
Downtown Indianapolis
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9.4/10 Exceptional! (487 reviews)
I was down here at the Indianapolis 500. The prices were really good and the hotel was very nice. I even got to meet Mario Andretti, who is staying at the hotel. what else can be said….

Reviewed on Jul 18, 2025

Hampton Inn Indianapolis Downtown IUPUI

Hampton Inn Indianapolis Downtown IUPUI

2.5 out of 5
Downtown Indianapolis
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
8.8/10 Excellent! (620 reviews)
Convenient location. Good experience overall.

Reviewed on Jul 18, 2025

Homewood Suites by Hilton Indianapolis Downtown IUPUI

Homewood Suites by Hilton Indianapolis Downtown IUPUI

3 out of 5
Downtown Indianapolis
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9.2/10 Wonderful! (532 reviews)
I didnt like pay $100 for parking

Reviewed on Jul 15, 2025

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Discover the most popular places to visit in Winchester

Winchester Speedway

4/5(16 reviews)

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

Winchester Speedway

Winchester Golf Club

3.5/5(4 reviews)

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

Winchester Golf Club

Winchester Hotel Deals

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 Jul 20 to Jul 21
$121 total
Jul 20 - Jul 21
Total includes taxes and fees
8.8/10 Excellent! (226 reviews)
"The property was very nice. Beds comfy"

Reviewed on Jun 25, 2025

Randolph Inn and Suites
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! (174 reviews)
Very roomy and family friendly home
"Our immediate family of 12 adults and 9 kids stayed at this home. It had enough bedrooms and bathrooms to make our experience very relaxing. The pool was a big hit for everyone. It rained at times but having the pool inside didn’t hinder our fun. Lots of outside space for baseball and kickball and ..."

Reviewed on Jul 14, 2025

Get rates
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
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
$59 nightly
The price is $66 total per night from Jul 22 to Jul 23
$66 total
Jul 22 - Jul 23
Total includes taxes and fees
6.6/10 (832 reviews)
"Nice clean room"

Reviewed on Jul 14, 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.

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

How much does a Winchester vacation package cost?
You'll find cheap prices from $264 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.