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Leesburg Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Leesburg vacation rentals

A room with a view of a lake, a dining table with chairs, a lamp, and a window with curtains.

1. Lovely 3 bedroom waterfront home on Irish lake part of the Barbee Chain of Lakes

Lovely 3 bedroom waterfront home on Irish lake part of the Barbee Chain of Lakes
Leesburg
$594 nightly
The price is $665
Oct 16 - Oct 17
Total with taxes and fees
Lovely 3 bedroom waterfront home on Irish lake part of the Barbee Chain of Lakes
A bedroom with a large mirror, a brown chair with a white pillow, a potted plant, and a window with blinds.

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

Lake Wawasee, Outdoor TV, Surround Sound, Bikes
Syracuse
10.0 out of 10, Exceptional, (12 reviews)
"Very nice and clean. Enjoyed our stay! Great location! "
United States
Becky J.
$341 nightly
The price is $377
Nov 4 - Nov 5
Total with taxes and fees
Lake Wawasee, Outdoor TV, Surround Sound, Bikes
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)
"The property was excellent, very clean and exactly what we expected. However we wanted to fish and kayak. The dock we were told to use was not even a little bit accessible to use . The hot tub was fabulous."
United States
Nicole C.
$306 nightly
The price is $343
Oct 9 - Oct 10
Total with taxes and fees
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
A hot tub with wooden benches, a TV screen displaying streaming services, and a covered patio area.

4. 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.
$358 nightly
The price is $400
Oct 12 - Oct 13
Total with taxes and fees
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
A lakeside patio with outdoor seating and a fire pit.

5. 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.
$485 nightly
The price is $543
Oct 11 - Oct 12
Total with taxes and fees
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.

6. 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, (2 reviews)
"Place is amazing. We will be back!"
United States
Patrick L.
$318 nightly
The price is $356
Oct 12 - Oct 13
Total with taxes and fees
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.

7. Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake
Pierceton
9.8 out of 10, Exceptional, (27 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
$251 nightly
The price is $281
Oct 11 - Oct 12
Total with taxes and fees
Cozy lakefront home on Big Barbee Lake
A covered porch with wooden flooring, two chairs, a table, and a window with blinds.

8. Trail Side in the Heart of Winona Lake

Trail Side in the Heart of Winona Lake
Winona Lake
9.8 out of 10, Exceptional, (67 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
$239 nightly
The price is $268
Oct 19 - Oct 20
Total with taxes and fees
Trail Side in the Heart of Winona Lake
A cabin with a wooden deck, a front door, and a garage.

9. 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.
$319 nightly
The price is $357
Oct 11 - Oct 12
Total with taxes and fees
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A room with a sofa, a wicker basket, and a view of an outdoor area with a fence and a building.

10. Barbee Lake Lodge/kayaks

Barbee Lake Lodge/kayaks
Warsaw
$256 nightly
The price is $287
Oct 11 - Oct 12
Total with taxes and fees
Barbee Lake Lodge/kayaks
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.
$405 nightly
The price is $453
Oct 9 - Oct 10
Total with taxes and fees
Lakefront Fun on Papakeechie - Kayaks & More!
A lakeside property with a dock, boats, and a grassy area with outdoor seating.

12. Heart Jacuzzi · Kayaks · Firepit · Pier

Heart Jacuzzi · Kayaks · Firepit · Pier
Warsaw
10.0 out of 10, Exceptional, (18 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.
$264 nightly
The price is $282
Oct 14 - Oct 15
Total with taxes and fees
Heart Jacuzzi · Kayaks · Firepit · Pier
Living area

13. Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!

Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
North Webster
$555 nightly
The price is $622
Nov 2 - Nov 3
Total with taxes and fees
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
A room with a large window, two bean bags, a small round table, and two stools.

14. 4BR Lakefront · Pier · Game Room · Sleeps 16+

4BR Lakefront · Pier · Game Room · Sleeps 16+
North Webster
10.0 out of 10, Exceptional, (26 reviews)
"The lake view is amazing and the house was plenty big for our 3 families that went. Everything was labeled so many extra things for fun! We had a blast on the lily pad!"
United States
Tammy M.
$557 nightly
The price is $594
Oct 14 - Oct 15
Total with taxes and fees
4BR Lakefront · Pier · Game Room · Sleeps 16+
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.
$944 nightly
The price is $1,057
Oct 18 - Oct 19
Total with taxes and fees
Best Views of Webster Lake! Paddleboards + Swimming
Living area

16. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
$180 nightly
The price is $202
Nov 1 - Nov 2
Total with taxes and fees
Quiet cul-de-sac home near Syracuse
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.
$594 nightly
The price is $665
Oct 20 - Oct 21
Total with taxes and fees
Premier Lake Wawasee Lakefront Home - Private Dock & Sandy Bottom
A living room with a ceiling fan, a black sofa, a black cabinet, and a sign that says 'LIVE LAUGH LOVE'.

18. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
$356 nightly
The price is $399
Oct 11 - Oct 12
Total with taxes and fees
Backwater Lake Cottage | Tiki Bar & Paddleboat
A modern living room with a sofa, chairs, a coffee table, a TV, and a bookshelf.

19. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
$267 nightly
The price is $286
Oct 12 - Oct 13
Total with taxes and fees
Indigo Hideaway | Romantic + Fire pit
A modern kitchen with white cabinets and a wooden dining table.

20. 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.
$802 nightly
The price is $898
Oct 16 - Oct 17
Total with taxes and fees
Lake Wawasee/HOT TUB/GAME ROOM/PONTOON/PICKLEBALL
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

Quality Inn & Suites Goshen

Quality Inn & Suites Goshen

10/10 Excellent
"We have been staying at the Quality since September 14th do to a house fire. This is family owned and ran. Staff is super friendly. Very clean, breakfast every morning. They have made our stay as easy and s comfortable as possible. Highly recommend."
Aaron 3-night trip
Posted 4 hours ago
Quality Inn & Suites Goshen

Find out more about Leesburg

Everything you need to know about Leesburg vacation rentals

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

Leesburg vacation 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 low season months. For more hustle and bustle, you may prefer to visit Leesburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $266 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Leesburg rentals

At Expedia, we put the best Leesburg vacation 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 vacation.

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 vacation rentals in Leesburg?

Yes, you can find vacation rentals near well known sights in Leesburg, or you can go with a secluded option if you're looking for relaxation.

What's the top vacation rental that Leesburg has to offer?

Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks: Visitors like this Leesburg vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Leesburg?

With 14 Expedia vacation rentals, you're sure 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 vacation rental in Leesburg like?

Vacation rentals are private properties you can stay in for a long or short time in Leesburg. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.