Winona Lake Vacation Rentals

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Vacation Rentals in Winona Lake

Exterior
Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake

Winona Lake
9.8 out of 10, Exceptional, (38)
"This is a fantastic property. Very clean and comfortable! Great neighborhood for walking and close to shops and restaurants. Will definitely stay here again."
United States
Eric B.
$236 nightly
The price is $264
Dec 3 - Dec 4
Total with taxes and fees
Trail Side in the Heart of Winona Lake
Property grounds
Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat

Pierceton
10.0 out of 10, Exceptional, (22)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
$247 nightly
The price is $265
Dec 3 - Dec 4
Total with taxes and fees
Fishing · Kayaks · Firepit · Paddleboat
Game room
Pony Creek Cottage

Pony Creek Cottage

North Manchester
10.0 out of 10, Exceptional, (11)
"Our work traveling crew really liked this property and will be staying again. "
United States
Charles W.
$274 nightly
The price is $307
Dec 18 - Dec 19
Total with taxes and fees
Pony Creek Cottage
Microwave, oven, stovetop
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Syracuse
9.8 out of 10, Exceptional, (6)
"The cottage fits the description perfectly! It was probably the cleanest place I've ever stayed, which meant so much. It is as nice outside as in. Will definitely book again for a quiet weekend away."
United States
Ryan B.
$233 nightly
The price is $261
Dec 28 - Dec 29
Total with taxes and fees
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Dining
Woodside Retreat in the Heart of Amish Country

Woodside Retreat in the Heart of Amish Country

Nappanee
10.0 out of 10, Exceptional, (11)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
United States
VICKI
$184 nightly
The price is $197
Jan 2 - Jan 3, 2026
Total with taxes and fees
Woodside Retreat in the Heart of Amish Country
Exterior
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain

3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain

Pierceton
9.6 out of 10, Exceptional, (14)
"This isn't our first time staying here and we love it. It's easy to find, simple living and quiet. Also, there is food delivery available so we don't have to cook after a long hunt."
United States
Michael G.
$269 nightly
The price is $301
Dec 5 - Dec 6
Total with taxes and fees
3 bedroom 2 bath renovated A frame on channel to Kuhn lake and the Barbee Chain
Interior
Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier

Warsaw
10.0 out of 10, Exceptional, (11)
"Was a wonderful weekend get-away for the wife and I. Quiet, relaxing, and stress free but with everything we needed. "
United States
Ed R.
$260 nightly
The price is $281
Dec 3 - Dec 4
Total with taxes and fees
Heart Jacuzzi · Kayaks · Firepit · Pier
Exterior
Gram's Cottage on Lake Webster in North Webster, Indiana is the perfect getaway.

Gram's Cottage on Lake Webster in North Webster, Indiana is the perfect getaway.

North Webster
$303 nightly
The price is $340
Dec 3 - Dec 4
Total with taxes and fees
Gram's Cottage on Lake Webster in North Webster, Indiana is the perfect getaway.
Exterior
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

Warsaw
10.0 out of 10, Exceptional, (17)
"Wonderful home, lovely views on the lake, great communication with owner and host. We very much enjoyed our stay!"
United States
Carol B.
$278 nightly
The price is $311
Dec 21 - Dec 22
Total with taxes and fees
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Outdoor pool
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

Milford
10.0 out of 10, Exceptional, (29)
"We had a really great time and the host was very very responsive to all our questions. "
United States
Mary B.
$326 nightly
The price is $365
Dec 3 - Dec 4
Total with taxes and fees
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Fridge, microwave, oven, stovetop
Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake

Pierceton
10.0 out of 10, Exceptional, (12)
"we had a great time!"
United States
Tamara H.
$236 nightly
The price is $264
Dec 3 - Dec 4
Total with taxes and fees
Cozy lakefront home on Big Barbee Lake
Property grounds
3-BR + Firepit, Coffee Bar & Grill

3-BR + Firepit, Coffee Bar & Grill

Bourbon
10.0 out of 10, Exceptional, (1)
"Our stay was perfect, starting with communication, spotless, decorated for FALL and it felt like we were at home! Our son’s college was 24 minutes from the house and it worked out perfect for him to come visit and us enjoy Family Weekend at the school to watch him play baseball! Our next visit will be this exact place! We hope to get to come at Christmas because we want to see how beautiful it’s decorated in Christmas! 10/10 stay! Sweetest Host! The basket of smores and apples was the best! "
United States
Brandy T.
$254 nightly
The price is $285
Dec 9 - Dec 10
Total with taxes and fees
3-BR + Firepit, Coffee Bar & Grill
Smart TV, fireplace
Lake access directly in front of Cottage on high speed watercraft Big Barbee

Lake access directly in front of Cottage on high speed watercraft Big Barbee

Pierceton
10.0 out of 10, Exceptional, (2)
Lake access directly in front of Cottage on high speed watercraft Big Barbee
Outdoor dining
4BR Lakefront · Pier · Game Room · Sleeps 16+

4BR Lakefront · Pier · Game Room · Sleeps 16+

North Webster
10.0 out of 10, Exceptional, (16)
"Excellent lakehouse on lake Webster! Our family loved staying at this property and the owners take care of all the details. From water rafts, kayaks, air hockey, and Foosball, this is the house to choose for a large family stay, and I highly recommend it!"
United States
dpersky1
$631 nightly
The price is $677
Dec 3 - Dec 4
Total with taxes and fees
4BR Lakefront · Pier · Game Room · Sleeps 16+
Dining
Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat

Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat

Syracuse
10.0 out of 10, Exceptional, (2)
"Great views, spacious, clean home, responsive owner. "
United States
Bob T.
$489 nightly
The price is $548
Dec 7 - Dec 8
Total with taxes and fees
Private Lake Front Home on Wawasee - Exclusive and Quiet Ogden Island Retreat
Property grounds
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

Leesburg
10.0 out of 10, Exceptional, (1)
"Fantastic place to get away right on the water. Enjoyed our 3 day stay with my husband and our puppy. There is a fenced in yard and a dock. Wonderful place to relax. Our host was very helpful and easy to get in touch with.Recommend highly "
United States
Lenora F.
$457 nightly
The price is $512
Dec 24 - Dec 25
Total with taxes and fees
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
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.
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Top Winona Lake Hotel Reviews

Blisspoint Inn Columbia City

Blisspoint Inn Columbia City

10/10 Excellent
"Friendly staff "
Julio 1-night trip
Posted 3 days ago
Blisspoint Inn Columbia City

Find out more about Winona Lake

Everything you need to know about Winona Lake vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winona Lake vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona Lake vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winona Lake vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona Lake. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winona Lake in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $188 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winona Lake rentals

At Expedia, we put the best Winona Lake vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winona Lake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona Lake vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona Lake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Winona Lake?

Yes, we give you a choice of vacation rentals close to the most popular attractions in Winona Lake, or you can select a more secluded option if you're looking for relaxation. Winona Lake is known for its lake views and sporting events. Make sure you have time to check out the forests while you're in the area.

What are some of the best vacation home rentals that Winona Lake has to offer?

Lake Wawasee Retreat: private pool, hot tub & pier: This vacation home rental outside of Winona Lake is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Winona Lake?

Choose from 7 Expedia vacation rentals in Winona Lake for a memorable vacation.

What can I see and do in Winona Lake?

Winona Lake and Winona Lake Trails Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Billy Sunday Home Museum and Winona Lake Limitless Park.

What are vacation rentals like in Winona Lake?

Vacation rentals are private properties you can book for a short or long stay in Winona Lake. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.