Winchester Vacations from $460

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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.
Homewood Suites by Hilton Indianapolis Downtown IUPUI

Homewood Suites by Hilton Indianapolis Downtown IUPUI

3 out of 5
Downtown Indianapolis
Price was $616, price is now $460 per person
$460
per person
Dec 24 - Dec 29
just found
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
9.2/10 Wonderful! (626 reviews)
Large room, clean, friendly staff

Reviewed on Nov 1, 2025

InterContinental Indianapolis by IHG

InterContinental Indianapolis by IHG

4 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $821, price is now $532 per person
$532
per person
Dec 24 - Dec 29
just found
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
9.4/10 Exceptional! (80 reviews)
Really nice hotel!!!

Reviewed on Aug 17, 2025

Embassy Suites by Hilton Indianapolis Downtown

Embassy Suites by Hilton Indianapolis Downtown

3.5 out of 5
Downtown Indianapolis
Save 100% on your flight
Price was $744, price is now $494 per person
$494
per person
Dec 24 - Dec 29
just found
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
8.4/10 Very Good! (1,011 reviews)
This hotel was very comfy, clean and located in a great area. There were a lot of dining options with bars, shopping and the Lucas oil stadium nearby. The rooms were bigger than I thought which was a plus. My bf and I will easily stay there again

Reviewed on Oct 25, 2025

Courtyard by Marriott Indianapolis Downtown

Courtyard by Marriott Indianapolis Downtown

3 out of 5
Downtown Indianapolis
Price was $691, price is now $494 per person
$494
per person
Dec 24 - Dec 29
just found
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
9/10 Wonderful! (1,041 reviews)
Easy parking, helpful staff.

Reviewed on Oct 27, 2025

Fairfield Inn & Suites by Marriott Indianapolis Downtown

Fairfield Inn & Suites by Marriott Indianapolis Downtown

3 out of 5
Downtown Indianapolis
Price was $691, price is now $494 per person
$494
per person
Dec 24 - Dec 29
just found
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
9/10 Wonderful! (1,006 reviews)
All was as to be expected. Relatively small room but comfortable bed. WiFi was very poor.

Reviewed on Oct 31, 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

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA

Winchester
9.6/10 Exceptional! (181 reviews)
Very nice, large, and clean. Plenty of space for everyone! Only downfall house is very musty especially the basement and chlorine smell from the pool. Cost was a bit high for 10 adults and 2 children for 2 nights was almost 5000 but in then end it was worth it. Hosts are very lovely and great communication. ...

Reviewed on Sep 29, 2025

Get rates
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
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 Nov 2 to Nov 3
$121 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (241 reviews)
Breakfast was good.the staff very friendly and the other hotel guest very friendly

Reviewed on Oct 28, 2025

Randolph Inn and Suites
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

2.5 out of 5
912 Mendleson Dr, Richmond, IN
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Nov 2 to Nov 3
$94 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (1,010 reviews)
Clean room, friendly staff, breakfast to order on Sunday morning

Reviewed on Oct 29, 2025

Baymont by Wyndham Richmond I-70
See all 113 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 $460 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.