Leesburg Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Leesburg holiday rentals

A lakeside view with a dock, boats, and a gazebo.

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 HK$2,210
HK$5,580 total
includes taxes & fees
9 Nov - 10 Nov
Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!
A building with a covered outdoor area, a staircase leading to the entrance, and a lawn in the foreground.

2. 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 HK$1,513
HK$2,986 total
includes taxes & fees
17 Nov - 18 Nov
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
A hot tub with wooden benches, a TV screen displaying streaming services, and a covered patio area.

3. 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 HK$1,061
HK$2,700 total
includes taxes & fees
9 Nov - 10 Nov
Winter Extravaganza!! Hot tub, huge game room + MORE!!
A two-story house with a covered porch, a front door, and a small front yard with shrubs.

4. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
3.0 star property
Syracuse
The price is HK$1,411
HK$3,728 total
includes taxes & fees
6 Dec - 7 Dec
Waterfront Family Gem w/ Private Dock in Syracuse
A black house with a patio area featuring outdoor furniture and a grill.

5. 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 HK$1,442
HK$2,608 total
includes taxes & fees
20 Nov - 21 Nov
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
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.
The price is HK$2,173
HK$4,042 total
includes taxes & fees
8 Nov - 9 Nov
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
A modern living room with a flat-screen TV, a sofa, a coffee table, and a blue patterned rug.

7. 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.
The price is HK$1,312
HK$2,717 total
includes taxes & fees
8 Nov - 9 Nov
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
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.
The price is HK$1,255
HK$2,179 total
includes taxes & fees
9 Nov - 10 Nov
Cozy lakefront home on Big Barbee Lake
Living area

9. 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 HK$1,787
HK$4,702 total
includes taxes & fees
17 Nov - 18 Nov
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
A covered porch with wooden flooring, two chairs, a table, and a window with blinds.

10. 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 HK$1,059
HK$1,915 total
includes taxes & fees
9 Nov - 10 Nov
Trail Side in the Heart of Winona Lake
A wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

11. 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 HK$1,345
HK$3,274 total
includes taxes & fees
7 Nov - 8 Nov
Lakefront Fun on Papakeechie - Kayaks & More!
A two-story house with a covered porch, a front door, and a small front yard with shrubs.

12. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
Syracuse
The price is HK$1,066
HK$3,608 total
includes taxes & fees
16 Nov - 17 Nov
Waterfront Family Gem w/ Private Dock in Syracuse
A cabin with a wooden deck, a front door, and a garage.

13. 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 HK$1,412
HK$2,653 total
includes taxes & fees
8 Nov - 9 Nov
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A lakeside property with a dock, boats, and a grassy area with outdoor seating.

14. 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 HK$1,265
HK$2,434 total
includes taxes & fees
11 Nov - 12 Nov
Heart Jacuzzi · Kayaks · Firepit · Pier
Terrace/patio

15. 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
A modern two-story house with a sloped roof, a front porch, and a well-maintained lawn.

16. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
The price is HK$1,130
HK$2,392 total
includes taxes & fees
9 Nov - 10 Nov
Indigo Hideaway | Romantic + Fire pit
A modern kitchen with a central island, bar stools, a dining table with chairs, and a view of the outdoors.

17. Turtle Alley on Wawasee

Turtle Alley on Wawasee
Syracuse
The price is HK$1,761
HK$4,090 total
includes taxes & fees
17 Nov - 18 Nov
Turtle Alley on Wawasee
Exterior

18. Your home @ Jellystone Pierceton, lot 525.

Your home @ Jellystone Pierceton, lot 525.
Pierceton
The price is HK$1,568
HK$1,905 total
includes taxes & fees
20 Nov - 21 Nov
Your home @ Jellystone Pierceton, lot 525.
A modern living room with a dining area, large windows, and a surfboard mounted on the wall.

19. 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 HK$2,863
HK$4,639 total
includes taxes & fees
7 Dec - 8 Dec
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
A lakeside dock with boats, a white van, and a wooden fence.

20. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is HK$1,270
HK$3,166 total
includes taxes & fees
8 Nov - 9 Nov
Backwater Lake Cottage | Tiki Bar & Paddleboat
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

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
cabin image
Cabins
Cabins

Find out more about Leesburg

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

  • View our selection of featured holiday rentals in Leesburg
  • Use the map to find apartments and other holiday homes in the Leesburg neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Leesburg while they last

Look no further and take a look at our great range of rental properties in Leesburg!

Frequently Asked Questions

Are there holiday rentals in Leesburg?

Yes, there are holiday rentals close to the most popular sights in Leesburg, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Leesburg has to offer?

Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks: This holiday home rental outside of Leesburg is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Leesburg?

With 14 Expedia holiday rentals, you're guaranteed to find just the right place for your Leesburg stay.

What’s there to see and do in Leesburg?

Tippecanoe Lake and Big Barbee Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Stanton Lake and Oppenheim Woods are other places worth a visit.

What’s a holiday rental in Leesburg like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Leesburg. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.