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Holiday Homes in Leesburg

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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 Leesburg holiday homes

A dining area with a wooden table and black chairs, a fireplace with a decorative tile surround, and a large mirror on the wall.

1. Sawmill Lakefront - Dock + Kayaks + Firepit

Sawmill Lakefront - Dock + Kayaks + Firepit
Warsaw
Sawmill Lakefront - Dock + Kayaks + Firepit
A hot tub with wooden benches, a TV screen displaying streaming services, and a covered patio area.

2. 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 covered porch with wooden flooring, two chairs, a table, and a window with blinds.

3. Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (65 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 €241
includes taxes & fees
30 Sept - 1 Oct
Trail Side in the Heart of Winona Lake
A house with a dock extending into a pond, surrounded by trees and other houses.

4. 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 €248
includes taxes & fees
11 Oct - 12 Oct
Cozy lakefront home on Big Barbee Lake
Living area

5. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
The price is €181
includes taxes & fees
30 Sept - 1 Oct
Quiet cul-de-sac home near Syracuse
A modern living room with a sofa, chairs, a coffee table, a TV, and a bookshelf.

6. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
The price is €256
includes taxes & fees
5 Oct - 6 Oct
Indigo Hideaway | Romantic + Fire pit
A lakeside patio with outdoor seating and a fire pit.

7. 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 €470
includes taxes & fees
30 Sept - 1 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.

8. 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 €338
includes taxes & fees
30 Sept - 1 Oct
Lakefront Fun on Papakeechie - Kayaks & More!
A living room with a ceiling fan, a black sofa, a black cabinet, and a sign that says 'LIVE LAUGH LOVE'.

9. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is €335
includes taxes & fees
30 Sept - 1 Oct
Backwater Lake Cottage | Tiki Bar & Paddleboat
A cabin with a wooden deck, a front door, and a garage.

10. 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 €317
includes taxes & fees
30 Sept - 1 Oct
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A room with a large window, two bean bags, a small round table, and two stools.

11. 4BR Lakefront · Pier · Game Room · Sleeps 16+

4BR Lakefront · Pier · Game Room · Sleeps 16+
North Webster
10.0 out of 10, Exceptional, (25 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 €580
includes taxes & fees
30 Sept - 1 Oct
4BR Lakefront · Pier · Game Room · Sleeps 16+
A covered outdoor seating area with wooden chairs and tables, overlooking a body of water with docks and boats.

12. Notre Dame Home games / Experience Lakefront Life

Notre Dame Home games / Experience Lakefront Life
Bremen
10.0 out of 10, Exceptional, (48 reviews)
"Absolutely incredible stay! the property is full of thoughtful touches from a truly caring host. Perfect for families! Lake of the woods is such a nice area and was the best way to relax after coming in from a large family reunion. Beautiful fully fenced backyard that is waterfront, comfortable rooms, and a responsive host. I couldn’t recommend this place more "
United States
danielle b.
The price is €201
includes taxes & fees
30 Sept - 1 Oct
Notre Dame Home games / Experience Lakefront Life
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.
The price is €920
includes taxes & fees
30 Sept - 1 Oct
Best Views of Webster Lake! Paddleboards + Swimming
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 €602
includes taxes & fees
12 Oct - 13 Oct
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
A covered porch with two chairs and a table, a brick wall, and string lights.

15. Superb 5-bedroom farmhouse in Goshen with WiFi, AC

Superb 5-bedroom farmhouse in Goshen with WiFi, AC
Goshen
9.8 out of 10, Exceptional, (53 reviews)
"We had a great stay!!"
United States
Sally F.
The price is €259
includes taxes & fees
30 Sept - 1 Oct
Superb 5-bedroom farmhouse in Goshen with WiFi, AC
A brown front door with a glass panel and a welcome sign. A 'HOME' sign is mounted on the wall to the left.

16. Amish Alley Guesthouse (Close to Topeka Livestock Auction)

Amish Alley Guesthouse (Close to Topeka Livestock Auction)
Topeka
9.4 out of 10, Exceptional, (3 reviews)
"Everything was great. Nice cozy home. The only downside was the shower was too small. If it had at least another half bathroom would be perfect."
United States
Mario
The price is €229
includes taxes & fees
24 Oct - 25 Oct
Amish Alley Guesthouse (Close to Topeka Livestock Auction)
A log cabin interior with a dining area, a living room, a staircase, and a coffee bar.

17. Hidden Log Cabin Hot Tub Ping Pong Family

Hidden Log Cabin Hot Tub Ping Pong Family
2.0 star property
Middlebury
The price is €326
includes taxes & fees
30 Sept - 1 Oct
Hidden Log Cabin Hot Tub Ping Pong Family
A modern kitchen with white cabinets and a wooden dining table.

18. 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 €921
includes taxes & fees
16 Oct - 17 Oct
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL
A long table with candles and greenery, set against a wooden backdrop with vertical strings of lights.

19. Rock Run Creek House

Rock Run Creek House
Goshen
9.6 out of 10, Exceptional, (5 reviews)
"was a fantastic rental. Thank you so much!"
United States
Lavern Y.
The price is €601
includes taxes & fees
5 Oct - 6 Oct
Rock Run Creek House
A dining area with a large table, chairs, and a chandelier.

20. The Heron House @Waldron Lake

The Heron House @Waldron Lake
Wawaka
9.8 out of 10, Exceptional, (34 reviews)
"Excellant place to stay. Great for small children. "
United States
Shelly S.
The price is €596
includes taxes & fees
12 Oct - 13 Oct
The Heron House @Waldron Lake
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 Leesburg Hotel Reviews

Holiday Inn Express & Suites Warsaw - E Center by IHG

Holiday Inn Express & Suites Warsaw - E Center by IHG

10/10 Excellent
"Great stay, as usual."
Lisa 1-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Warsaw - E Center by IHG

Find out more about Leesburg

Leesburg Holiday Homes information

Number of reviews
271
Accommodation
132 Holiday Homes
Lowest Price
€181
Highest Price
€921