Holiday Homes in Leesburg

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Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Leesburg holiday homes

1. 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 NZ$1,324
includes taxes & fees
15 Nov - 16 Nov
Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!

2. 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.
The price is NZ$643
includes taxes & fees
16 Nov - 17 Nov
Winter Extravaganza!! Hot tub, huge game room + MORE!!

3. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
Syracuse
The price is NZ$793
includes taxes & fees
16 Nov - 17 Nov
Waterfront Family Gem w/ Private Dock in Syracuse

4. 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 NZ$483
includes taxes & fees
15 Nov - 16 Nov
Cozy lakefront home on Big Barbee Lake

5. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
10.0 out of 10, Exceptional, (1 review)
"Outstanding property. Very well organized and maintained"
United States
John
The price is NZ$527
includes taxes & fees
16 Nov - 17 Nov
Indigo Hideaway | Romantic + Fire pit

6. 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$606
includes taxes & fees
15 Nov - 16 Nov
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain

7. 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 NZ$439
includes taxes & fees
1 Dec - 2 Dec
Trail Side in the Heart of Winona Lake

8. Lake Wawasee, Outdoor TV, Surround Sound, Bikes

Lake Wawasee, Outdoor TV, Surround Sound, Bikes
Syracuse
10.0 out of 10, Exceptional, (12 reviews)
"Great set up. Love to come back next year for work because the house was comfortable and convenient!"
United States
J.D. M.
Lake Wawasee, Outdoor TV, Surround Sound, Bikes

9. 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$759
includes taxes & fees
14 Nov - 15 Nov
Lakefront Fun on Papakeechie - Kayaks & More!

10. 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$924
includes taxes & fees
15 Nov - 16 Nov
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

11. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is NZ$748
includes taxes & fees
25 Nov - 26 Nov
Backwater Lake Cottage | Tiki Bar & Paddleboat

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 NZ$1,312
includes taxes & fees
8 Dec - 9 Dec
Best Views of Webster Lake! Paddleboards + Swimming

13. Wawasee Retreat w/ Golf Cart & 1- min Lake Access

Wawasee Retreat w/ Golf Cart & 1- min Lake Access
Cromwell
The price is NZ$467
includes taxes & fees
16 Nov - 17 Nov
Wawasee Retreat w/ Golf Cart & 1- min Lake Access

14. Turtle Alley on Wawasee

Turtle Alley on Wawasee
Syracuse
The price is NZ$935
includes taxes & fees
14 Nov - 15 Nov
Turtle Alley on Wawasee

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, (56 reviews)
"We had a great stay!!"
United States
Sally F.
The price is NZ$660
includes taxes & fees
15 Nov - 16 Nov
Superb 5-bedroom farmhouse in Goshen with WiFi, AC

16. Games at Notre Dame's home grounds / Experience life by the lake

Games at Notre Dame's home grounds / Experience life by the lake
Bremen
10.0 out of 10, Exceptional, (48 reviews)
"What a great stay! It was perfect for our family and the hosts were wonderful. We’d definitely stay again."
United States
Kathleen N.
The price is NZ$386
includes taxes & fees
15 Nov - 16 Nov
Games at Notre Dame's home grounds / Experience life by the lake

17. Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras
Goshen
10.0 out of 10, Exceptional, (16 reviews)
"The host was so wonderful, accommodating and helpful during the entire process. The home was beautiful and fit our group well. The pool was nice and warm in the middle of winter! "
United States
Kala Y.
The price is NZ$1,939
includes taxes & fees
18 Nov - 19 Nov
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras

18. Spacious 5-bedroom house in soothing Millersburg with AC

Spacious 5-bedroom house in soothing Millersburg with AC
Millersburg
Spacious 5-bedroom house in soothing Millersburg with AC

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

Amish Alley Guesthouse (Close to Topeka Livestock Auction)
Topeka
9.2 out of 10, Wonderful, (5 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 NZ$488
includes taxes & fees
14 Nov - 15 Nov
Amish Alley Guesthouse (Close to Topeka Livestock Auction)

20. Rock Run Creek House

Rock Run Creek House
Goshen
9.6 out of 10, Exceptional, (5 reviews)
"Close to Shipshe and a beautiful property"
United States
Holly A.
The price is NZ$1,128
includes taxes & fees
15 Nov - 16 Nov
Rock Run Creek House
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.