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

Holiday Homes in Winona Lake

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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, (66 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 €236
includes taxes & fees
14 Oct - 15 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, (27 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
The price is €252
includes taxes & fees
5 Oct - 6 Oct
Cozy lakefront home on Big Barbee Lake
A living room with a ceiling fan, a black sofa, a black cabinet, and a sign that says 'LIVE LAUGH LOVE'.

3. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is €358
includes taxes & fees
15 Oct - 16 Oct
Backwater Lake Cottage | Tiki Bar & Paddleboat
A cabin with a wooden deck, a front door, and a garage.

4. 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 €321
includes taxes & fees
5 Oct - 6 Oct
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A lakeside patio with outdoor seating and a fire pit.

5. 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 €472
includes taxes & fees
15 Oct - 16 Oct
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Living area

6. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
Quiet cul-de-sac home near Syracuse
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 €388
includes taxes & fees
15 Oct - 16 Oct
Lakefront Fun on Papakeechie - Kayaks & More!
A hot tub with wooden benches, a TV screen displaying streaming services, and a covered patio area.

8. 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, (38 reviews)
"Everything was very clean and we loved the layout of the house and the game room!"
United States
Rachel A.
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
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 €323
includes taxes & fees
4 Oct - 5 Oct
Pony Creek Cottage
A room with a large window, two bean bags, a small round table, and two stools.

10. 4BR Lakefront · Pier · Game Room · Sleeps 16+

4BR Lakefront · Pier · Game Room · Sleeps 16+
North Webster
10.0 out of 10, Exceptional, (26 reviews)
"The property is fantastic and perfect for large families. We easily slept 14. Lots of extras like a paddle boat, kayaks, life jackets, games. We had a great time during our 5 night stay! Pontoon was rented from Aloha and they were great, too."
United States
Tiha K.
The price is €588
includes taxes & fees
4 Oct - 5 Oct
4BR Lakefront · Pier · Game Room · Sleeps 16+
A grassy outdoor area with a fire pit and four Adirondack chairs.

11. Lovely 3 bedroom waterfront home on Irish lake part of the Barbee Chain of Lakes

Lovely 3 bedroom waterfront home on Irish lake part of the Barbee Chain of Lakes
Leesburg
The price is €707
includes taxes & fees
15 Oct - 16 Oct
Lovely 3 bedroom waterfront home on Irish lake part of the Barbee Chain of Lakes
Terrace/patio

12. 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 €925
includes taxes & fees
15 Oct - 16 Oct
Best Views of Webster Lake! Paddleboards + Swimming
A modern living room with a sofa, chairs, a coffee table, a TV, and a bookshelf.

13. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
Indigo Hideaway | Romantic + Fire pit
A modern living room with a dining area, large windows, and a surfboard mounted on the wall.

14. 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 €603
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.

15. 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 €801
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.
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Top Winona Lake Hotel Reviews

CountrySide Inn

CountrySide Inn

8/10 Good
"No issues with this location."
Scott 3-night trip
Posted 10 hours ago
CountrySide Inn

Find out more about Winona Lake

Winona Lake Holiday Homes information

Number of reviews
169
Accommodation
105 Holiday Homes
Lowest Price
€236
Highest Price
€925