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Leesburg Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Leesburg vacation rentals

A dining area with a wooden table and black chairs, a fireplace with a decorative tile surround, and a large mirror on the wall.

1. Sawmill Lakefront - Dock + Kayaks + Firepit

Sawmill Lakefront - Dock + Kayaks + Firepit
Warsaw
The price is AED 698
AED 1,514 total
includes taxes & fees
12 Oct - 13 Oct
Sawmill Lakefront - Dock + Kayaks + Firepit
A black house with a patio area featuring outdoor furniture and a grill.

2. 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 AED 676
AED 1,209 total
includes taxes & fees
1 Oct - 2 Oct
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.

3. 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.
The price is AED 441
AED 1,026 total
includes taxes & fees
1 Oct - 2 Oct
Heart Jacuzzi · Kayaks · Firepit · Pier
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.
The price is AED 423
AED 1,231 total
includes taxes & fees
2 Oct - 3 Oct
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
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, (66 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 AED 496
AED 975 total
includes taxes & fees
6 Oct - 7 Oct
Trail Side in the Heart of Winona Lake
A wooden deck with picnic tables and a view of a lake.

6. Fishing · Kayaks · Firepit · Paddleboat

Fishing · Kayaks · Firepit · Paddleboat
Pierceton
10.0 out of 10, Exceptional, (32 reviews)
"Clean property, gewat location, loved the lake and the stars."
United States
joseph b.
The price is AED 415
AED 993 total
includes taxes & fees
1 Oct - 2 Oct
Fishing · Kayaks · Firepit · Paddleboat
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, (26 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
The price is AED 533
AED 1,020 total
includes taxes & fees
5 Oct - 6 Oct
Cozy lakefront home on Big Barbee Lake
A wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

8. 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 AED 511
AED 1,439 total
includes taxes & fees
1 Oct - 2 Oct
Lakefront Fun on Papakeechie - Kayaks & More!
A modern living room with a sofa, chairs, a coffee table, a TV, and a bookshelf.

9. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
The price is AED 467
AED 1,050 total
includes taxes & fees
5 Oct - 6 Oct
Indigo Hideaway | Romantic + Fire pit
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)
"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 AED 1,017
AED 1,995 total
includes taxes & fees
4 Oct - 5 Oct
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Living area

11. Quiet cul-de-sac home near Syracuse

Quiet cul-de-sac home near Syracuse
Syracuse
Quiet cul-de-sac home near Syracuse
A small, single-story building with a porch, outdoor seating, and a view of the surrounding trees.

12. Barbee Lake Lodge/kayaks

Barbee Lake Lodge/kayaks
Warsaw
The price is AED 643
AED 1,053 total
includes taxes & fees
1 Oct - 2 Oct
Barbee Lake Lodge/kayaks
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 AED 661
AED 1,312 total
includes taxes & fees
2 Oct - 3 Oct
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A modern living room with a flat-screen TV, a sofa, a coffee table, and a blue patterned rug.

14. 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.
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
A living room with a ceiling fan, a black sofa, a black cabinet, and a sign that says 'LIVE LAUGH LOVE'.

15. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
The price is AED 551
AED 1,465 total
includes taxes & fees
1 Oct - 2 Oct
Backwater Lake Cottage | Tiki Bar & Paddleboat
A room with a large window, two bean bags, a small round table, and two stools.

16. 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 property is fantastic and perfect for large families. We easily slept 14. Lots of extras like a paddle boat, kayaks, life jackets, games. We had a great time during our 5 night stay! Pontoon was rented from Aloha and they were great, too."
United States
Tiha K.
The price is AED 1,047
AED 2,403 total
includes taxes & fees
1 Oct - 2 Oct
4BR Lakefront · Pier · Game Room · Sleeps 16+
A compact kitchen with white cabinets, a black stove, and a microwave.

17. Cozy cottage cabin with fire pit ,lake and beach access Indiana

Cozy cottage cabin with fire pit ,lake and beach access Indiana
Albion
The price is AED 381
AED 571 total
includes taxes & fees
1 Oct - 2 Oct
Cozy cottage cabin with fire pit ,lake and beach access Indiana
A covered outdoor seating area with wooden chairs and tables, overlooking a body of water with docks and boats.

18. Notre Dame Home games / Experience Lakefront Life

Notre Dame Home games / Experience Lakefront Life
Bremen
10.0 out of 10, Exceptional, (48 reviews)
"Absolutely incredible stay! the property is full of thoughtful touches from a truly caring host. Perfect for families! Lake of the woods is such a nice area and was the best way to relax after coming in from a large family reunion. Beautiful fully fenced backyard that is waterfront, comfortable rooms, and a responsive host. I couldn’t recommend this place more "
United States
danielle b.
The price is AED 657
AED 843 total
includes taxes & fees
1 Oct - 2 Oct
Notre Dame Home games / Experience Lakefront Life
Terrace/patio

19. 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 AED 1,686
AED 3,883 total
includes taxes & fees
1 Oct - 2 Oct
Best Views of Webster Lake! Paddleboards + Swimming
A covered porch with two chairs and a table, a brick wall, and string lights.

20. 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, (53 reviews)
"We had a great stay!!"
United States
Sally F.
The price is AED 915
AED 1,085 total
includes taxes & fees
1 Oct - 2 Oct
Superb 5-bedroom farmhouse in Goshen with WiFi, AC
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

Fairfield Inn & Suites by Marriott Goshen

Fairfield Inn & Suites by Marriott Goshen

8/10 Good
"Overall, it was great. Easy check in, clean, and well maintained. However, breakfast was not very good and the room temperature was not well regulated. It would cool down, but got really warm before it would kick back on and there was no way to leave the fan on to keep the air moving."
Laura 1-night trip
Posted 13 hours ago
Fairfield Inn & Suites by Marriott Goshen

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.