Winchester Vacations from $303

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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.
Comfort Suites Southport

Comfort Suites Southport

2.5 out of 5
Price was $397, price is now $303 per person
$303
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Indianapolis (IND)
8.2/10 Very Good! (945 reviews)
All around good stay. Well maintained, nice staff, comfortable mattress, clean, hot water was instant. Will stay here again.

Reviewed on Nov 28, 2025

Hilton Garden Inn Indianapolis Downtown

Hilton Garden Inn Indianapolis Downtown

3.5 out of 5
Downtown Indianapolis
Price was $727, price is now $537 per person
$537
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Indianapolis (IND)
9.2/10 Wonderful! (71 reviews)
staff was great! social shout out to Jaden at front desk.

Reviewed on Dec 7, 2025

Bottleworks Hotel

Bottleworks Hotel

4.5 out of 5
Downtown Indianapolis
Price was $880, price is now $669 per person
$669
per person
Jan 16 - Jan 18
found 17 hours ago
Roundtrip flight included
Houston (IAH) to Indianapolis (IND)
9.8/10 Exceptional! (1,664 reviews)
Nice room and seemed way nicer than i thought it would be.

Reviewed on Dec 7, 2025

Sleep Inn Indianapolis East

Sleep Inn Indianapolis East

2.5 out of 5
Price was $404, price is now $311 per person
$311
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Indianapolis (IND)
8/10 Very Good! (1,473 reviews)
Many areas were not very clean.

Reviewed on Nov 25, 2025

Hampton Inn Indianapolis Northwest - Park 100

Hampton Inn Indianapolis Northwest - Park 100

2.5 out of 5
Price was $386, price is now $314 per person
$314
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Indianapolis (IND)
8.8/10 Excellent! (944 reviews)
Great counter support. Clean room. Helpful during visit. Great breakfast.

Reviewed on Dec 6, 2025

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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

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 IN
9.6/10 Exceptional! (183 reviews)
We had a wonderful, memorable stay. Communication about expectations for guests was easy. I appreciated the couple hours earlier than normal check in time since our son was arriving from his college about an hour away. There is plenty of space for a big group and despite the colder than average Thanksgiving ...

Reviewed on Dec 3, 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 Dec 8 to Dec 9
$121 total
Dec 8 - Dec 9
Total with taxes and fees
8.8/10 Excellent! (243 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
$67 nightly
The price is $75 total per night from Dec 12 to Dec 13
$75 total
Dec 12 - Dec 13
Total with taxes and fees
8.2/10 Very Good! (1,018 reviews)
Clean comfortable room, convenient location

Reviewed on Nov 30, 2025

Baymont by Wyndham Richmond I-70
See all 132 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 $303 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.