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Leesburg Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Leesburg holiday rentals

A flat surface with a pattern of stars and stripes, possibly a table or board, on a grassy area with trees and a building in the background.

1. Updated and spacious 4-bedroom house on Tippecanoe Lake

Updated and spacious 4-bedroom house on Tippecanoe Lake
Leesburg
The price is AU$784
includes taxes & fees
8 Sept - 9 Sept
Updated and spacious 4-bedroom house on Tippecanoe Lake
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, (37 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 black house with a patio area featuring outdoor furniture and a grill.

3. 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
9.6 out of 10, Exceptional, (17 reviews)
"Lovely little place to stay"
United States
Panacea G.
The price is AU$479
includes taxes & fees
8 Sept - 9 Sept
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
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, (16 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 AU$439
includes taxes & fees
10 Sept - 11 Sept
Heart Jacuzzi · Kayaks · Firepit · Pier
A covered porch with wooden flooring, two chairs, a table, and a window with blinds.

5. Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (59 reviews)
"Interior decoration was excellent. Appliances all appeared to be new."
United States
Beth
The price is AU$353
includes taxes & fees
8 Sept - 9 Sept
Trail Side in the Heart of Winona Lake
A house with a dock extending into a pond, surrounded by trees and other houses.

6. Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake
Pierceton
9.6 out of 10, Exceptional, (25 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
The price is AU$391
includes taxes & fees
10 Sept - 11 Sept
Cozy lakefront home on Big Barbee Lake
A wooden deck with picnic tables and a view of a lake.

7. Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat
Pierceton
10.0 out of 10, Exceptional, (28 reviews)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
The price is AU$399
includes taxes & fees
13 Sept - 14 Sept
Fishing · Kayaks · Firepit · Paddleboat
A cabin with a wooden deck, a front door, and a garage.

8. 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, (22 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 AU$493
includes taxes & fees
10 Sept - 11 Sept
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

9. Lakefront Fun on Papakeechie - Kayaks & More!

Lakefront Fun on Papakeechie - Kayaks & More!
Syracuse
10.0 out of 10, Exceptional, (1 review)
"Beautiful location and views! The hosts have thought of everything a visitor might need. Only caveat, not for those with mobility issues due to steep walkway and interior stairs. Exceeded my expectations. Would absolutely stay there again."
United States
Karen E.
The price is AU$560
includes taxes & fees
8 Sept - 9 Sept
Lakefront Fun on Papakeechie - Kayaks & More!
A lakeside patio with outdoor seating and a fire pit.

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)
"Fantastic place to get away right on the water. Enjoyed our 3 day stay with my husband and our puppy. There is a fenced in yard and a dock. Wonderful place to relax. Our host was very helpful and easy to get in touch with.Recommend highly "
United States
Lenora F.
The price is AU$760
includes taxes & fees
8 Sept - 9 Sept
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
A modern kitchen with a dining table set for four, a built-in oven, and a large window providing natural light.

11. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
The price is AU$404
includes taxes & fees
15 Sept - 16 Sept
Indigo Hideaway | Romantic + Fire pit
A modern living room with a flat-screen TV, a sofa, a coffee table, and a blue patterned rug.

12. 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, (1 review)
"Nice five minute walk to beach and restaurants. So excellent location. The added amenities were great as we used the provided pickel ball paddles and inflatable watercraft."
United States
Jonathan J.
The price is AU$502
includes taxes & fees
10 Sept - 11 Sept
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
A living room with a black leather sofa, a dining table with chairs, and a kitchen area in the background.

13. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is AU$567
includes taxes & fees
22 Sept - 23 Sept
Backwater Lake Cottage | Tiki Bar & Paddleboat

14. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
The price is AU$288
includes taxes & fees
8 Sept - 9 Sept
Quiet cul-de-sac home near Syracuse

15. 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 AU$901
includes taxes & fees
1 Oct - 2 Oct
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
A rustic log cabin with a porch and a stone foundation.

16. Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!

Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!
Goshen
9.6 out of 10, Exceptional, (19 reviews)
"Visited family and stayed a couple nights. Cozy place to stay. "
United States
Ken L.
The price is AU$573
includes taxes & fees
4 Oct - 5 Oct
Cozy, chic & historic 3-bedroom cabin in trendy Goshen, 40 mins from Notre Dame!
A modern living room with a dining area, large windows, and a surfboard mounted on the wall.

17. 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 AU$878
includes taxes & fees
21 Sept - 22 Sept
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom

18. 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 AU$1,402
includes taxes & fees
13 Sept - 14 Sept
Best Views of Webster Lake! Paddleboards + Swimming
A modern living room with a sofa, armchairs, a coffee table, and a ceiling fan.

19. Lakeside Indiana Vacation Rental Near Fort Wayne!

Lakeside Indiana Vacation Rental Near Fort Wayne!
3.0 star property
Churubusco
10.0 out of 10, Exceptional, (2 reviews)
"This home had absolutely EVERYTHING we needed for a long weekend by the lake. Kitchen is fully stocked, beds are comfortable, the yard has a swing and lots of birds, and the fire pit made the nights sooo relaxing. The property is a short walk away from the local campground- we rented a pontoon from them and had a great time on the lake. This place is perfect for a relaxing and peaceful vacation. 100 stars!!! "
United States
Arianna
The price is AU$405
includes taxes & fees
15 Sept - 16 Sept
Lakeside Indiana Vacation Rental Near Fort Wayne!
A log cabin interior with a dining area, a living room with a sofa and armchair, a coffee bar, and a wooden staircase.

20. Hidden Log Cabin | Hot Tub | Ping Pong | Family |

Hidden Log Cabin | Hot Tub | Ping Pong | Family |
Goshen
10.0 out of 10, Exceptional, (16 reviews)
"Such a lovely place!It was spotless and peaceful"
United States
Marilee G.
The price is AU$455
includes taxes & fees
10 Sept - 11 Sept
Hidden Log Cabin | Hot Tub | Ping Pong | Family |
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 Hotel & Suites Plymouth by IHG

Holiday Inn Express Hotel & Suites Plymouth by IHG

10/10 Excellent
"The hotel management has really put a lot of work into improvements at this hotel. The rooms have been renovated. The checkin is much smoother. The shower works perfectly and is just the right temperature. The provided toiletries are fully stocked. The breakfast is well above average. The staff is very friendly and accomodating. I come every year for the Blueberry Festival and I stay at this hotel each time. There are not many choices for a stay in Plymouth, but IHG makes it worth it."
Glenn 1-night trip
Posted 1 hour ago
Holiday Inn Express Hotel & Suites Plymouth by IHG

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 favourite 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 depend 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 AU$353 per night. Entering your travel dates in the search wizard might find you 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?

3-bedroom lake front house on the Barbee Chain of Lakes in amazing Leesburg.: This highly rated holiday home rental in Leesburg has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Our travellers also rate Tippy Cottage on the Lake as a favourite home for rent in Leesburg.

How many holiday rentals are there in Leesburg?

With 12 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.