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Leesburg Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 lakeside property with a dock, boats, and a grassy area with outdoor seating.

2. 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.
$266 nightly
The price is $284
Oct 19 - Oct 20
Total with taxes and fees
Heart Jacuzzi · Kayaks · Firepit · Pier
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
9.4 out of 10, Exceptional, (18 reviews)
"Lovely little place to stay"
United States
Panacea G.
$309 nightly
The price is $346
Oct 15 - Oct 16
Total with taxes and fees
Cozy lake Cottage on Dewart Lake , 1 mile from Blue Barn Berry Farm, Hottub!
A modern living room with a sofa, chairs, a coffee table, a TV, and a bookshelf.

4. Indigo Hideaway | Romantic + Fire pit

Indigo Hideaway | Romantic + Fire pit
Nappanee
$267 nightly
The price is $286
Oct 15 - Oct 16
Total with taxes and fees
Indigo Hideaway | Romantic + Fire pit
A house with a dock extending into a pond, surrounded by trees and other houses.

5. Cozy lakefront home on Big Barbee Lake

Cozy lakefront home on Big Barbee Lake
Pierceton
9.8 out of 10, Exceptional, (28 reviews)
"Very enjoyable place to rest and relax after tournament musky fishing."
United States
Michael A.
$250 nightly
The price is $280
Oct 18 - Oct 19
Total with taxes and fees
Cozy lakefront home on Big Barbee 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, (33 reviews)
"We had a wondeful week at the cottage. One of the cleanest that we have been to which I really appreciate. Communication was great."
United States
Amy G.
$251 nightly
The price is $267
Oct 19 - Oct 20
Total with taxes and fees
Fishing · Kayaks · Firepit · Paddleboat
A covered porch with wooden flooring, two chairs, a table, and a window with blinds.

7. 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
$235 nightly
The price is $263
Oct 19 - Oct 20
Total with taxes and fees
Trail Side in the Heart of Winona Lake
A bedroom with a large mirror, a brown chair with a white pillow, a potted plant, and a window with blinds.

8. 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.
$307 nightly
The price is $339
Oct 15 - Oct 16
Total with taxes and fees
Lake Wawasee, Outdoor TV, Surround Sound, Bikes
A modern living room with a flat-screen TV, a sofa, a coffee table, and a blue patterned rug.

9. 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.
$320 nightly
The price is $358
Oct 18 - Oct 19
Total with taxes and fees
Dog-Friendly 2BR | Private Fenced Yard & Fire Pit | Walk to Village & Grace
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
10.0 out of 10, Exceptional, (1 review)
"Beautiful place, right on the canal. Clean and well equipped with everything we needed. Really enjoyed our stay."
United States
Kim W.
$250 nightly
The price is $280
Oct 15 - Oct 16
Total with taxes and fees
Barbee Lake Lodge/kayaks
A cabin with a wooden deck, a front door, and a garage.

11. 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.
$318 nightly
The price is $356
Oct 24 - Oct 25
Total with taxes and fees
Charming 3 bedroom 2 bath A frame home on channel to Kuhn Lake & Barbee Chain
A living room with a ceiling fan, a black sofa, a black cabinet, and a sign that says 'LIVE LAUGH LOVE'.

12. Backwater Lake Cottage | Tiki Bar & Paddleboat

Backwater Lake Cottage | Tiki Bar & Paddleboat
North Webster
$356 nightly
The price is $399
Oct 15 - Oct 16
Total with taxes and fees
Backwater Lake Cottage | Tiki Bar & Paddleboat
A lakeside patio with outdoor seating and a fire pit.

13. 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 18 - Oct 19
Total with taxes and fees
Beautiful Lakefront home, pets welcome, fully fenced, dock, kayaks, fishing!!
Living area

14. 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 wooden deck with a table and chairs, overlooking a lake, surrounded by trees.

15. 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.
$379 nightly
The price is $424
Nov 3 - Nov 4
Total with taxes and fees
Lakefront Fun on Papakeechie - Kayaks & More!
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, (27 reviews)
"A fantastic stay! The house was fully equipped to make our stay enjoyable and relaxing. The host was very accommodating."
United States
Patrick K.
$551 nightly
The price is $587
Oct 15 - Oct 16
Total with taxes and fees
4BR Lakefront · Pier · Game Room · Sleeps 16+
Exterior

17. Your home @ Jellystone Pierceton, lot 525.

Your home @ Jellystone Pierceton, lot 525.
Pierceton
$226 nightly
The price is $253
Oct 16 - Oct 17
Total with taxes and fees
Your home @ Jellystone Pierceton, lot 525.
Living area

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

Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
North Webster
$527 nightly
The price is $590
Nov 9 - Nov 10
Total with taxes and fees
Charlee's Cabin - Family Escape on Webster Lake | Pier & Swimming!
A modern building with large windows, a fire pit, outdoor seating, and a staircase leading to a deck.

19. Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana

Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana
Albion
8.0 out of 10, Very good, (1 review)
"Very quiet location. Relaxing deck to sit on. Fire pit and grill were stocked with charcoal and firewood which was appreciated. Pet friendly. Close to a lot of lakes and recreation areas. Communication was great with the host."
United States
Joan P.
$139 nightly
The price is $155
Oct 31 - Nov 1
Total with taxes and fees
Autumn getaway cozy cottage cabin with fire pit ,lake and beach access Indiana
A bedroom with a bed, striped bedding, a wall-mounted lamp, and a decorative vase.

20. Designer Apartment-Walkable Downtown Goshen

Designer Apartment-Walkable Downtown Goshen
Goshen
10.0 out of 10, Exceptional, (1 review)
"First, the property is DARLING!!! It was exactly as pictured. We came in for a wedding and it was a block away from the venue. PERFECT. The price was good. Communication from the host was TOP NOTCH. The bed was comfortable. There is a Keurig coffee machine. There is a steamer for your clothing. ***It should be noted that Goshen has a steady stream of trains going through 24/27. If noise bothers you bring a white noise machine or ear plugs. The downtown location (which is very convenient) is also...
United States
Kelly A.
$198 nightly
The price is $212
Oct 19 - Oct 20
Total with taxes and fees
Designer Apartment-Walkable Downtown Goshen
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

Amish Inn

Amish Inn

10/10 Excellent
"Very accommodating staff. They went above and beyond."
Jennifer 1-night trip
Posted 1 day ago
Amish Inn

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 $263 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.