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

Winona Lake Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winona Lake holiday 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, (71 reviews)
"Fabulous place to stay! Great location, easily accessible to anything you need or want to see in Winona Lake and surrounding areas. The house very clean and comfortable and safe. Thank you, had a wonderful time."
United States
Shea
The price is AU$357
includes taxes & fees
9 Nov - 10 Nov
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, (3 reviews)
"Place is amazing. We will be back!"
United States
Patrick L.
The price is AU$499
includes taxes & fees
8 Nov - 9 Nov
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
A building with a covered outdoor area, a staircase leading to the entrance, and a lawn in the foreground.

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

Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Warsaw
9.8 out of 10, Exceptional, (42 reviews)
"Very Good place to stay"
United States
Alex K.
The price is AU$511
includes taxes & fees
1 Dec - 2 Dec
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
A lakeside property with a dock, boats, and a grassy area with outdoor seating.

4. Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier
Warsaw
10.0 out of 10, Exceptional, (19 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.
The price is AU$439
includes taxes & fees
17 Nov - 18 Nov
Heart Jacuzzi · Kayaks · Firepit · Pier
A lakeside view with a dock, boats, and a gazebo.

5. Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!

Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!
Leesburg
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful views and full of amenities. Absolutely perfect for our group. Great communication from the host."
United States
Wendy S.
The price is AU$1,039
includes taxes & fees
9 Nov - 10 Nov
Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!
A lakeside patio with outdoor seating and a fire pit.

6. 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)
"This guest house was perfect for two people, though it could sleep six. It was clean and had all the amenities we needed. We had a very comfortable and relaxing stay there."
United States
Gretchen E.
The price is AU$743
includes taxes & fees
8 Nov - 9 Nov
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
A cabin with a wooden deck, a front door, and a garage.

7. 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, (24 reviews)
"Love this space! Clean and welcoming! Super host, great to work with! Looking forward to our next stay! "
United States
John K.
The price is AU$489
includes taxes & fees
11 Nov - 12 Nov
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A house with a dock extending into a pond, surrounded by trees and other houses.

8. Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake
Pierceton
9.8 out of 10, Exceptional, (31 reviews)
"Great little spot for my mother, brother and myself. It is a quiet area, too!"
United States
Allison M.
The price is AU$399
includes taxes & fees
8 Nov - 9 Nov
Cozy lakefront home on Big Barbee Lake
Exterior

9. Your home @ Jellystone Pierceton, lot 525.

Your home @ Jellystone Pierceton, lot 525.
Pierceton
The price is AU$346
includes taxes & fees
8 Nov - 9 Nov
Your home @ Jellystone Pierceton, lot 525.
A wooden deck with picnic tables and a view of a lake.

10. Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat
Pierceton
10.0 out of 10, Exceptional, (36 reviews)
"We enjoyed the cute cottage, and really appreciated all the nice little touches that made it so welcoming."
United States
Kim S.
The price is AU$392
includes taxes & fees
8 Nov - 9 Nov
Fishing · Kayaks · Firepit · Paddleboat
A hot tub with wooden benches, a TV screen displaying streaming services, and a covered patio area.

11. Winter Extravaganza!! Hot tub, huge game room + MORE!!

Winter Extravaganza!! Hot tub, huge game room + MORE!!
Milford
10.0 out of 10, Exceptional, (39 reviews)
"Everything was very clean and we loved the layout of the house and the game room!"
United States
Rachel A.
The price is AU$511
includes taxes & fees
1 Dec - 2 Dec
Winter Extravaganza!! Hot tub, huge game room + MORE!!
A black house with a patio area featuring outdoor furniture and a grill.

12. 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
9.4 out of 10, Exceptional, (19 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is AU$475
includes taxes & fees
14 Nov - 15 Nov
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
Living area

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

Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
North Webster
The price is AU$862
includes taxes & fees
18 Nov - 19 Nov
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
A two-story house with a covered porch, a front door, and a small front yard with shrubs.

14. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
3.0 star property
Syracuse
The price is AU$686
includes taxes & fees
9 Nov - 10 Nov
Waterfront Family Gem w/ Private Dock in Syracuse
A lakeside dock with boats, a white van, and a wooden fence.

15. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is AU$579
includes taxes & fees
8 Nov - 9 Nov
Backwater Lake Cottage | Tiki Bar & Paddleboat
A hallway with a wooden floor, a chandelier, a dining area with a table and chairs, and a large window with colorful panes.

16. Pony Creek Cottage

Pony Creek Cottage
North Manchester
10.0 out of 10, Exceptional, (14 reviews)
"Our work traveling crew really liked this property and will be staying again. "
United States
Charles W.
The price is AU$435
includes taxes & fees
8 Nov - 9 Nov
Pony Creek Cottage
A stone fireplace with a fire, surrounded by various board games and a plant.

17. Wawasee Retreat w/ Golf Cart & 1- min Lake Access

Wawasee Retreat w/ Golf Cart & 1- min Lake Access
Cromwell
The price is AU$357
includes taxes & fees
10 Nov - 11 Nov
Wawasee Retreat w/ Golf Cart & 1- min Lake Access
A wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

18. Lakefront Fun on Papakeechie - Kayaks & More!

Lakefront Fun on Papakeechie - Kayaks & More!
Syracuse
10.0 out of 10, Exceptional, (2 reviews)
"This location has a very beautiful view"
United States
Jennie S.
The price is AU$593
includes taxes & fees
9 Nov - 10 Nov
Lakefront Fun on Papakeechie - Kayaks & More!
A modern kitchen with a central island, bar stools, a dining table with chairs, and a view of the outdoors.

19. Turtle Alley on Wawasee

Turtle Alley on Wawasee
Syracuse
The price is AU$753
includes taxes & fees
8 Nov - 9 Nov
Turtle Alley on Wawasee
A two-story house with a covered porch, a front door, and a small front yard with shrubs.

20. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
Syracuse
The price is AU$656
includes taxes & fees
19 Nov - 20 Nov
Waterfront Family Gem w/ Private Dock in Syracuse
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winona Lake Hotel Reviews

Oakwood Resort

Oakwood Resort

10/10 Excellent
"This is the place to Stay! And if you go To the restaurant, definitely ask for Grace! She is wonderful and will definitely tell you the best items to get on the menu! Such a sweet person!"
Jackie 3-night trip
Posted 14 hours ago
Oakwood Resort

Find out more about Winona Lake

Everything you need to know about Winona Lake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona Lake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winona Lake holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona Lake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona Lake holiday rentals we have selected for you start as low as AU$357 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winona Lake rentals

At Expedia, we put the best Winona Lake holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Winona Lake?

Yes, there are holiday rentals close to the most popular sights in Winona Lake, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Winona Lake has to offer?

The Boat House w/ Dock: Enjoy Lake Life!: This holiday home rental outside of Winona Lake is located on the waterfront, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Winona Lake?

Choose from 9 Expedia holiday rentals in Winona Lake for a memorable holiday.

What can I see and do in Winona Lake?

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

What are holiday rentals like in Winona Lake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winona Lake. Holiday rentals feature amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.