Winchester Vacations from $174

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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.
Baymont by Wyndham Indianapolis South

Baymont by Wyndham Indianapolis South

2.5 out of 5
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Indianapolis (IND)
7.4/10 Good! (333 reviews)
Needs updated and more and better parking

Reviewed on Jun 29, 2025

The Landing Apartments By Barsala

The Landing Apartments By Barsala

4 out of 5
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Indianapolis (IND)
9/10 Wonderful! (29 reviews)
Apartment was very well kept. But you definitely need to look into some sort of sound deading for the master bedroom window traffic noise was loud..

Reviewed on Jun 5, 2025

Holiday Inn Indianapolis Airport by IHG

Holiday Inn Indianapolis Airport by IHG

3 out of 5
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to Indianapolis (IND)
9.2/10 Wonderful! (1,012 reviews)
The transport to the airport was flexible and free. The staff was very friendly and helpful.

Reviewed on Jun 29, 2025

Fairfield Inn & Suites by Marriott Indianapolis Carmel

Fairfield Inn & Suites by Marriott Indianapolis Carmel

2.5 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Indianapolis (IND)
9.6/10 Exceptional! (530 reviews)
Very clean and nice area!

Reviewed on Jun 23, 2025

Hampton Inn & Suites Indianapolis-Keystone

Hampton Inn & Suites Indianapolis-Keystone

2.5 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Indianapolis (IND)
9.4/10 Exceptional! (888 reviews)
Clean. Spacious. Good breakfast.

Reviewed on Jun 30, 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 2 to Jul 3
$121 total
Jul 2 - Jul 3
Total includes taxes and fees
8.8/10 Excellent! (225 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! (172 reviews)
50th Anniversary Gathering
"We wanted a location to gather our whole family of 40 to celebrate our 50th anniversary and this fit the bill exactly. Far enough away from home to feel removed but close enough for reasonable travel. The owner was VERY responsive to an issue that popped up and took care of it immediately."

Reviewed on Jun 25, 2025

Get rates
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
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
$77 nightly
The price is $87 total per night from Jul 28 to Jul 29
$87 total
Jul 28 - Jul 29
Total includes taxes and fees
8/10 Very Good! (1,009 reviews)
One of the the best
"Very nice, people friendly and helpful. Clean easy access."

Reviewed on Jun 30, 2025

Baymont by Wyndham Richmond I-70
See all 116 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 $174 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.