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

Winona Lake Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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
$218 nightly
The price is $244
Nov 9 - Nov 10
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, (3 reviews)
"Place is amazing. We will be back!"
United States
Patrick L.
$301 nightly
The price is $337
Nov 8 - Nov 9
Total with taxes and fees
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.
$312 nightly
The price is $349
Dec 1 - Dec 2
Total with taxes and fees
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.
$289 nightly
The price is $310
Nov 11 - Nov 12
Total with taxes and fees
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.
$635 nightly
The price is $711
Nov 9 - Nov 10
Total with taxes and fees
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.
$447 nightly
The price is $501
Nov 8 - Nov 9
Total with taxes and fees
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.
$295 nightly
The price is $330
Nov 11 - Nov 12
Total with taxes and fees
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.
$231 nightly
The price is $259
Nov 9 - Nov 10
Total with taxes and fees
Cozy lakefront home on Big Barbee Lake
Exterior

9. Your home @ Jellystone Pierceton, lot 525.

Your home @ Jellystone Pierceton, lot 525.
Pierceton
$212 nightly
The price is $237
Nov 9 - Nov 10
Total with taxes and fees
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.
$255 nightly
The price is $272
Nov 8 - Nov 9
Total with taxes and fees
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.
$312 nightly
The price is $350
Dec 1 - Dec 2
Total with taxes and fees
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.
$287 nightly
The price is $321
Nov 8 - Nov 9
Total with taxes and fees
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
$505 nightly
The price is $565
Nov 23 - Nov 24
Total with taxes and fees
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
$425 nightly
The price is $476
Nov 8 - Nov 9
Total with taxes and fees
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
$360 nightly
The price is $404
Nov 8 - Nov 9
Total with taxes and fees
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.
$264 nightly
The price is $296
Nov 8 - Nov 9
Total with taxes and fees
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
$218 nightly
The price is $244
Nov 10 - Nov 11
Total with taxes and fees
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.
$373 nightly
The price is $418
Nov 8 - Nov 9
Total with taxes and fees
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
$456 nightly
The price is $511
Nov 8 - Nov 9
Total with taxes and fees
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
$398 nightly
The price is $446
Nov 8 - Nov 9
Total with taxes and fees
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 7 hours ago
Oakwood Resort

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 $244 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?

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.