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

Holiday Homes in Winona Lake

  • 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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winona Lake holiday homes

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, (63 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 NZ$459
includes taxes & fees
19 Oct - 20 Oct
Trail Side in the Heart of Winona Lake
A house with a dock extending into a pond, surrounded by trees and other houses.

2. Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake
Pierceton
9.8 out of 10, Exceptional, (26 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
The price is NZ$481
includes taxes & fees
27 Sept - 28 Sept
Cozy lakefront home on Big Barbee Lake
A cabin with a wooden deck, a front door, and a garage.

3. 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 NZ$612
includes taxes & fees
28 Sept - 29 Sept
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A living room with a black leather sofa, a dining table with chairs, and a kitchen area in the background.

4. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is NZ$668
includes taxes & fees
27 Sept - 28 Sept
Backwater Lake Cottage | Tiki Bar & Paddleboat
A grassy outdoor area with a hammock, kayaks, and a storage box with inflatable rings.

5. Sawmill Lakefront - Dock + Kayaks + Firepit

Sawmill Lakefront - Dock + Kayaks + Firepit
Warsaw
The price is NZ$757
includes taxes & fees
27 Sept - 28 Sept
Sawmill Lakefront - Dock + Kayaks + Firepit
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 NZ$921
includes taxes & fees
1 Oct - 2 Oct
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
A wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

7. 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 NZ$788
includes taxes & fees
5 Oct - 6 Oct
Lakefront Fun on Papakeechie - Kayaks & More!
A modern kitchen with a dining table set for four, a built-in oven, and a large window providing natural light.

8. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
The price is NZ$503
includes taxes & fees
25 Sept - 26 Sept
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.

9. Pony Creek Cottage

Pony Creek Cottage
North Manchester
10.0 out of 10, Exceptional, (12 reviews)
"Our work traveling crew really liked this property and will be staying again. "
United States
Charles W.
The price is NZ$606
includes taxes & fees
30 Sept - 1 Oct
Pony Creek Cottage

10. 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.
The price is NZ$1,806
includes taxes & fees
26 Sept - 27 Sept
Best Views of Webster Lake! Paddleboards + Swimming
A modern living room with a dining area, large windows, and a surfboard mounted on the wall.

11. 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.
The price is NZ$1,115
includes taxes & fees
20 Oct - 21 Oct
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
A modern kitchen with white cabinets and a wooden dining table.

12. 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.
The price is NZ$1,826
includes taxes & fees
16 Oct - 17 Oct
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.
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

Blisspoint Inn Columbia City

Blisspoint Inn Columbia City

10/10 Excellent
"N/A"
Tad 1-night trip
Posted 7 hours ago
Blisspoint Inn Columbia City

Find out more about Winona Lake

Winona Lake Holiday Homes information

Number of reviews
113
Accommodation
104 Holiday Homes
Lowest Price
NZ$459
Highest Price
NZ$1,826