Winona Lake Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Winona Lake Vacation

Our Winona Lake vacation packages let you customize your own adventure. Tailor your journey to your interests and style and make the most of your time in this fantastic city. If a sightseeing tour is part of the program during your trip to Winona Lake, look around popular attractions like Grace College, Chapman Lakes and Wagon Wheel Theatre. Expedia has what you need to escape the everyday. Tailor your vacation to Winona Lake to suit your style of travel, whatever that may be!

Stay near popular Winona Lake attractions

Billy Sunday Home Museum

Step back in time at this preserved home of early 20th-century evangelist Billy Sunday. Explore original furnishings and personal artifacts while guides illuminate his influential religious work.
See properties

Winona Lake Hotel Deals

Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake

Winona Lake IN
$239 nightly
The price is $268 total per night from Aug 3 to Aug 4
$268 total
Aug 3 - Aug 4
Total with taxes and fees
9.8/10 Exceptional! (49 reviews)
"Charming and immaculate, this 2 bedroom property had everything we needed and was perfect for our family. It's conveniently located just a short walk from a public beach, coffee shop, ice cream shop, restaurant and shopping on Winona Lake. The owner was friendly and responsive. We enjoyed evenings ..."

Reviewed on Jul 10, 2026

Trail Side in the Heart of Winona Lake
The Winona Lake Chalet 2

The Winona Lake Chalet 2

Winona Lake IN
10/10 Exceptional! (38 reviews)
"We enjoyed our stay… Property is close to all kinds of great activities and things to do for the family!"

Reviewed on Jul 9, 2026

Get rates
The Winona Lake Chalet 2
Charming Bungalow on Winona Lake Island

Charming Bungalow on Winona Lake Island

Winona Lake IN
Get rates
Charming Bungalow on Winona Lake Island
See all 227 properties in Winona Lake
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 Winona Lake Vacation Packages

Winona Lake Essential Information

Language
English
Currency
U.S dollars
Population
5,000
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Wagon Wheel Theatre, Tippecanoe Lake and Webster Lake

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winona Lake vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Winona Lake costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winona Lake?
If you'd like to book a cheap Winona Lake vacation package, consider traveling in November, December and January. You'll typically find lower prices on flights and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Winona Lake?
The ideal length for your Winona Lake vacation depends on what you'd like to do. Usually, a few days to a week will give you plenty of time to visit all the leading sights and explore some hidden gems along the way.
How to find the best Winona Lake package deals?
Use Expedia's filter tool to find some fabulous Winona Lake package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Winona Lake package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Winona Lake vacation as a package?
You can enjoy significant savings on your Winona Lake escape by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Winona Lake?
If you're planning a spur-of-the-moment Winona Lake trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Winona Lake vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Winona Lake break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.