An aerial view of a lakeside residential area with houses, a bridge, and a parking lot.

Winona Lake Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winona Lake vacation rentals

A covered porch with wooden flooring, two chairs, a table, and a window with blinds.

1. Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (59 reviews)
"Interior decoration was excellent. Appliances all appeared to be new."
United States
Beth
$222 nightly
The price is $248
Sep 8 - Sep 9
Total with taxes and fees
Trail Side in the Heart of Winona Lake
A modern living room with a flat-screen TV, a sofa, a coffee table, and a blue patterned rug.

2. Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace

Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
Winona Lake
10.0 out of 10, Exceptional, (1 review)
"Nice five minute walk to beach and restaurants. So excellent location. The added amenities were great as we used the provided pickel ball paddles and inflatable watercraft."
United States
Jonathan J.
$336 nightly
The price is $376
Sep 14 - Sep 15
Total with taxes and fees
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
A lakeside property with a dock, boats, and a grassy area with outdoor seating.

3. Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier
Warsaw
10.0 out of 10, Exceptional, (16 reviews)
"This cottage was very cute and cozy, a true lovers retreat. Host was very accommodating and check in and out was easy."
United States
Lisa S.
$292 nightly
The price is $314
Sep 10 - Sep 11
Total with taxes and fees
Heart Jacuzzi · Kayaks · Firepit · Pier
A wooden deck with picnic tables and a view of a lake.

4. Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat
Pierceton
10.0 out of 10, Exceptional, (28 reviews)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
$271 nightly
The price is $290
Sep 13 - Sep 14
Total with taxes and fees
Fishing · Kayaks · Firepit · Paddleboat
A house with a dock extending into a pond, surrounded by trees and other houses.

5. Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake
Pierceton
9.6 out of 10, Exceptional, (25 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
$233 nightly
The price is $260
Sep 10 - Sep 11
Total with taxes and fees
Cozy lakefront home on Big Barbee Lake
A cabin with a wooden deck, a front door, and a garage.

6. Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain

Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
Pierceton
9.8 out of 10, Exceptional, (22 reviews)
"Love this space! Clean and welcoming! Super host, great to work with! Looking forward to our next stay! "
United States
John K.
$316 nightly
The price is $354
Sep 10 - Sep 11
Total with taxes and fees
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A black house with a patio area featuring outdoor furniture and a grill.

7. Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!

Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
Syracuse
9.6 out of 10, Exceptional, (17 reviews)
"Lovely little place to stay"
United States
Panacea G.
$309 nightly
The price is $346
Sep 8 - Sep 9
Total with taxes and fees
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
A lakeside patio with outdoor seating and a fire pit.

8. 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, (5 reviews)
"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.
$482 nightly
The price is $540
Sep 8 - Sep 9
Total with taxes and fees
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
A living room with a black leather sofa, a dining table with chairs, and a kitchen area in the background.

9. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
$372 nightly
The price is $417
Sep 22 - Sep 23
Total with taxes and fees
Backwater Lake Cottage | Tiki Bar & Paddleboat
A wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

10. Lakefront Fun on Papakeechie - Kayaks & More!

Lakefront Fun on Papakeechie - Kayaks & More!
Syracuse
10.0 out of 10, Exceptional, (1 review)
"Beautiful location and views! The hosts have thought of everything a visitor might need. Only caveat, not for those with mobility issues due to steep walkway and interior stairs. Exceeded my expectations. Would absolutely stay there again."
United States
Karen E.
$363 nightly
The price is $406
Sep 8 - Sep 9
Total with taxes and fees
Lakefront Fun on Papakeechie - Kayaks & More!
A flat surface with a pattern of stars and stripes, possibly a table or board, on a grassy area with trees and a building in the background.

11. Updated and spacious 4-bedroom house on Tippecanoe Lake

Updated and spacious 4-bedroom house on Tippecanoe Lake
Leesburg
$503 nightly
The price is $563
Sep 8 - Sep 9
Total with taxes and fees
Updated and spacious 4-bedroom house on Tippecanoe Lake

12. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
$180 nightly
The price is $202
Sep 8 - Sep 9
Total with taxes and fees
Quiet cul-de-sac home near Syracuse

13. Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
North Webster
$602 nightly
The price is $675
Oct 1 - Oct 2
Total with taxes and fees
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
A modern kitchen with a dining table set for four, a built-in oven, and a large window providing natural light.

14. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
$273 nightly
The price is $292
Sep 15 - Sep 16
Total with taxes and fees
Indigo Hideaway | Romantic + Fire pit
A hallway with a wooden floor, a chandelier, a dining area with a table and chairs, and a large window with colorful panes.

15. Pony Creek Cottage

Pony Creek Cottage
North Manchester
10.0 out of 10, Exceptional, (11 reviews)
"Our work traveling crew really liked this property and will be staying again. "
United States
Charles W.
$317 nightly
The price is $355
Sep 30 - Oct 1
Total with taxes and fees
Pony Creek Cottage

16. Best Views of Webster Lake! Paddleboards + Swimming

Best Views of Webster Lake! Paddleboards + Swimming
North Webster
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely beautiful rental. We had such a wonderful time my son wants to come back again. Friendly people all around and beautiful sunrise we saw."
United States
John D.
$944 nightly
The price is $1,057
Sep 13 - Sep 14
Total with taxes and fees
Best Views of Webster Lake! Paddleboards + Swimming
A modern living room with a dining area, large windows, and a surfboard mounted on the wall.

17. Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom

Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
Syracuse
10.0 out of 10, Exceptional, (2 reviews)
"Great views, spacious, clean home, responsive owner. "
United States
Bob T.
$583 nightly
The price is $653
Sep 21 - Sep 22
Total with taxes and fees
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
A modern kitchen with white cabinets and a wooden dining table.

18. Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL

Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL
Cromwell
9.8 out of 10, Exceptional, (29 reviews)
"Went for a guys grouping outing and had a great time! Great location with lots of outdoor space for yard games etc!"
United States
Zakk R.
$953 nightly
The price is $1,068
Sep 18 - Sep 19
Total with taxes and fees
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL
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

Hampton Inn Warsaw

Hampton Inn Warsaw

8/10 Good
"Very convenient and comfortable."
Donna 2-night trip
Posted 18 hours ago
Hampton Inn Warsaw

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 $248 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?

Trail Side in the Heart of Winona Lake: This highly rated vacation home rental in Winona Lake is located on a lake and has a fireplace, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Winona Lake?

Choose from 8 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.