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

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, (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 ￥21,271
￥40,058 total
includes taxes & fees
Nov 11 - Nov 12
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, (2 reviews)
"Place is amazing. We will be back!"
United States
Patrick L.
The price is ￥26,355
￥52,634 total
includes taxes & fees
Nov 5 - Nov 6
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
A wooden deck with picnic tables and a view of a lake.

3. 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 ￥20,287
￥44,036 total
includes taxes & fees
Nov 8 - Nov 9
Fishing · Kayaks · Firepit · Paddleboat
A building with a covered outdoor area, a staircase leading to the entrance, and a lawn in the foreground.

4. 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 ￥27,568
￥56,694 total
includes taxes & fees
Dec 1 - Dec 2
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.

5. 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 ￥25,405
￥48,180 total
includes taxes & fees
Nov 4 - Nov 5
Heart Jacuzzi · Kayaks · Firepit · Pier
A house with a dock extending into a pond, surrounded by trees and other houses.

6. 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 ￥26,155
￥46,587 total
includes taxes & fees
Nov 16 - Nov 17
Cozy lakefront home on Big Barbee Lake
A covered outdoor area with a set of stairs leading to a door, a small table, and a view of the outside.

7. Barbee Lake Lodge/kayaks

Barbee Lake Lodge/kayaks
Warsaw
10.0 out of 10, Exceptional, (1 review)
"Beautiful place, right on the canal. Clean and well equipped with everything we needed. Really enjoyed our stay."
United States
Kim W.
Barbee Lake Lodge/kayaks
A black house with a patio area featuring outdoor furniture and a grill.

8. 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 ￥28,991
￥52,587 total
includes taxes & fees
Nov 4 - Nov 5
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
A cabin with a wooden deck, a front door, and a garage.

9. 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 ￥28,361
￥53,293 total
includes taxes & fees
Nov 8 - Nov 9
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A lakeside view with a dock, boats, and a gazebo.

10. 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 ￥44,393
￥112,074 total
includes taxes & fees
Nov 4 - Nov 5
Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!
A small outdoor bar with a wooden counter, three colorful chairs, and a sign that reads 'OPEN.'

11. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is ￥25,514
￥63,057 total
includes taxes & fees
Nov 4 - Nov 5
Backwater Lake Cottage | Tiki Bar & Paddleboat
A lakeside patio with outdoor seating and a fire pit.

12. 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 ￥43,644
￥81,175 total
includes taxes & fees
Nov 8 - Nov 9
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Terrace/patio

13. 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.
Best Views of Webster Lake! Paddleboards + Swimming
Exterior

14. Your home @ Jellystone Pierceton, lot 525.

Your home @ Jellystone Pierceton, lot 525.
Pierceton
The price is ￥31,512
￥38,117 total
includes taxes & fees
Nov 4 - Nov 5
Your home @ Jellystone Pierceton, lot 525.
A modern building with large windows, a fire pit, outdoor seating, and a staircase leading to a deck.

15. Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana

Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana
Albion
8.0 out of 10, Very good, (1 review)
"Very quiet location. Relaxing deck to sit on. Fire pit and grill were stocked with charcoal and firewood which was appreciated. Pet friendly. Close to a lot of lakes and recreation areas. Communication was great with the host."
United States
Joan P.
The price is ￥16,347
￥23,691 total
includes taxes & fees
Nov 30 - Dec 1
Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana
Living area

16. 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 ￥32,724
￥91,019 total
includes taxes & fees
Nov 23 - Nov 24
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
A hallway with a wooden floor, a chandelier, a dining area with a table and chairs, and a large window with colorful panes.

17. 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 ￥19,767
￥48,079 total
includes taxes & fees
Nov 4 - Nov 5
Pony Creek Cottage
A modern two-story house with a sloped roof, a front porch, and a well-maintained lawn.

18. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
The price is ￥22,687
￥46,192 total
includes taxes & fees
Nov 4 - Nov 5
Indigo Hideaway | Romantic + Fire pit
A two-story house with a covered porch, a front door, and a small front yard with shrubs.

19. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
3.0 star property
Syracuse
The price is ￥29,306
￥75,997 total
includes taxes & fees
Nov 4 - Nov 5
Waterfront Family Gem w/ Private Dock in Syracuse
A wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

20. 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 ￥27,044
￥67,758 total
includes taxes & fees
Nov 4 - Nov 5
Lakefront Fun on Papakeechie - Kayaks & More!
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

Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake

10/10 Excellent
"Excellent stay!"
Colleen R. 1-night trip
Posted 2 days ago
Trail Side in the Heart of Winona Lake

Find out more about Winona Lake

Search for holiday rentals in Winona Lake on Expedia! You can easily find your home rentals, villas, holiday apartments in Winona Lake using one of the methods below:

  • View our selection of featured holiday rentals in Winona Lake
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Look no further and take a look at our great range of rental properties in Winona Lake!

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?

The Boat House w/ Dock: Enjoy Lake Life!: This vacation home rental outside of Winona Lake is located on the waterfront and has a patio, 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 9 Expedia vacation rentals in Winona Lake for a memorable vacation.

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 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.