Leesburg Holiday Rentals

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Our top choices for Leesburg holiday rentals

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$1,330
includes taxes & fees
10 Nov - 11 Nov
Sunrise on Sawmill - Kayaks, Paddleboat, Firepit, Arcade!

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 NZ$641
includes taxes & fees
2 Dec - 3 Dec
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!

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 NZ$625
includes taxes & fees
11 Nov - 12 Nov
Winter Extravaganza!! Hot tub, huge game room + MORE!!

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 NZ$858
includes taxes & fees
10 Nov - 11 Nov
Waterfront Family Gem w/ Private Dock in Syracuse

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, (20 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is NZ$598
includes taxes & fees
10 Nov - 11 Nov
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!

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 NZ$931
includes taxes & fees
10 Nov - 11 Nov
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!

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 NZ$627
includes taxes & fees
10 Nov - 11 Nov
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace

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 NZ$474
includes taxes & fees
10 Nov - 11 Nov
Cozy lakefront home on Big Barbee Lake

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 NZ$1,005
includes taxes & fees
23 Nov - 24 Nov
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

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 NZ$459
includes taxes & fees
15 Nov - 16 Nov
Trail Side in the Heart of Winona Lake

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 NZ$745
includes taxes & fees
10 Nov - 11 Nov
Lakefront Fun on Papakeechie - Kayaks & More!

12. Waterfront Family Gem w/ Private Dock in Syracuse

Waterfront Family Gem w/ Private Dock in Syracuse
Syracuse
The price is NZ$816
includes taxes & fees
10 Nov - 11 Nov
Waterfront Family Gem w/ Private Dock in Syracuse

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 NZ$610
includes taxes & fees
11 Nov - 12 Nov
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain

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 NZ$560
includes taxes & fees
11 Nov - 12 Nov
Heart Jacuzzi · Kayaks · Firepit · Pier

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.
The price is NZ$1,316
includes taxes & fees
10 Nov - 11 Nov
Best Views of Webster Lake! Paddleboards + Swimming

16. 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$548
includes taxes & fees
10 Nov - 11 Nov
Indigo Hideaway | Romantic + Fire pit

17. Turtle Alley on Wawasee

Turtle Alley on Wawasee
Syracuse
The price is NZ$930
includes taxes & fees
10 Nov - 11 Nov
Turtle Alley on Wawasee

18. Your home @ Jellystone Pierceton, lot 525.

Your home @ Jellystone Pierceton, lot 525.
Pierceton
The price is NZ$418
includes taxes & fees
10 Nov - 11 Nov
Your home @ Jellystone Pierceton, lot 525.

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 NZ$1,051
includes taxes & fees
6 Dec - 7 Dec
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom

20. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is NZ$720
includes taxes & fees
10 Nov - 11 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.

Find holiday rentals that suit your style

Find out more about Leesburg

Everything you need to know about Leesburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Leesburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Leesburg holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Leesburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leesburg. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leesburg holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leesburg holiday rentals we have selected for you start as low as NZ$418 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Leesburg rentals

At Expedia, we put the best Leesburg holiday 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 Leesburg 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 Leesburg holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leesburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.