Leesburg Holiday Rentals

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Holiday Rentals in Leesburg

Lake Tippecanoe, Little Tippy retreat—sleeps 12, dog friendly, private lakefront
10.0 out of 10, Exceptional, (3)
"We had a wonderful time. The views from the deck and three upper bedrooms are beautiful. 10/10"
United States
Michelle F.
Lake Tippecanoe, Little Tippy retreat—sleeps 12, dog friendly, private lakefront
“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views
10.0 out of 10, Exceptional, (23)
"House had the perfect set up for our family and needs for our stay. We loved the view. We will be back!"
United States
Denise M.
“Stay Anchored” Lake Tippecanoe channel front with pier and great lake views
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
10.0 out of 10, Exceptional, (12)
The price is AU$484
includes taxes & fees
20 Oct - 21 Oct
Memorable Vacation Awaits on Big Chapman Lake! Sleeps 8! Optional Pontoon!
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
10.0 out of 10, Exceptional, (4)
"The hot tub was clean and ready to go as soon as we got there.. very relaxing stay… we loved it"
United States
Samantha T.
The price is AU$516
includes taxes & fees
20 Oct - 21 Oct
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm
Trail Side in the Heart of Winona Lake
10.0 out of 10, Exceptional, (33)
"House very comfortable, we enjoyed being close to the trails"
United States
Dennis A.
The price is AU$389
includes taxes & fees
27 Oct - 28 Oct
Trail Side in the Heart of Winona Lake
The Heron House @Waldron Lake
9.8 out of 10, Exceptional, (29)
"The owner was always very helpful and quick to answer any questions! The house was clean and very nice! Having the kayaks and paddle boat was so wonderful and the small sand beach worked well for our family!"
United States
cathy s.
The price is AU$970
includes taxes & fees
22 Oct - 23 Oct
The Heron House @Waldron Lake
Lakefront Home on Lake Webster
9.4 out of 10, Exceptional, (33)
"Very comfortable lakeside cottage with a beautiful view."
United States
Angela R.
Lakefront Home on Lake Webster
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks
10.0 out of 10, Exceptional, (9)
"Thoroughly enjoyed our week, the small lake was wonderful, and the home was exactly as listed. Every need was thought out by the owner of this place! Beautiful home, with lots of personal space and space for together time. "
United States
Kris M.
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks
Cozy lakefront home on Big Barbee Lake
10.0 out of 10, Exceptional, (10)
"Great location with everything you need for a weekend on the lake. We will definitely be back! "
United States
dunchbox 1.
The price is AU$411
includes taxes & fees
20 Oct - 21 Oct
Cozy lakefront home on Big Barbee Lake
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!
2.0 star property
10.0 out of 10, Exceptional, (6)
"Our family group of 14 really enjoyed this lake house. It had everything we needed. The outside areas were really nice & the game room was a real hit with kids & adults. Communication with host Joe was great. We hope to stay there again!!"
United States
Tami S.
Irish Lakefront, Hot Tub! Pets, dock, fishing, kayaks, ice fishing, hunting!
Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (161)
"Family stay."
United States
Tim S.
The price is AU$277
includes taxes & fees
26 Oct - 27 Oct
Charming farmhouse in peaceful countryside
Beautiful Skinner Cottage overlooking the lake
9.8 out of 10, Exceptional, (114)
"Wonderful time second time here will come back"
United States
william L.
Beautiful Skinner Cottage overlooking the lake
`Burning Pine Inn' Farm House in Amish country.
10.0 out of 10, Exceptional, (23)
"Awesome property, wonderful host, our kids loved visiting the horses every day! Looking forwarding to a future stay! Absolutely recommend!"
United States
Jonathan M.
`Burning Pine Inn' Farm House in Amish country.
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
10.0 out of 10, Exceptional, (119)
"Well appointed cottage, clean and quiet. We enjoyed our stay."
United States
EV O.
Beautiful and Historic Log Cabin: cozy, quiet, huge hot tub! Quiet getaway!
3 bedrooms sleeps up to 10 people
9.8 out of 10, Exceptional, (47)
"Excellent accommodations and location. Had a great time, absolutely no issues."
United States
Karl S.
3 bedrooms sleeps up to 10 people
Woodside Retreat in the Heart of Amish Country
10.0 out of 10, Exceptional, (9)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
United States
VICKI
The price is AU$309
includes taxes & fees
22 Oct - 23 Oct
Woodside Retreat in the Heart of Amish Country
Hilltop Family Retreat
10.0 out of 10, Exceptional, (1)
"Property appears to be recently remodeled and up to date with plenty of space for large groups. 3 bathrooms so no one has to wait. Upstairs can be warm during the summer but nothing a fan doesn't fix. Property owner is responsive and easy to reach."
United States
George M.
The price is AU$951
includes taxes & fees
20 Oct - 21 Oct
Hilltop Family Retreat
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath
10.0 out of 10, Exceptional, (54)
"Great cottage and view, definitely recommend."
United States
Nicholas S.
Lakefront Cottage on Webster Lake with Beautiful Sunsets, 2 bed, 1 bath
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras
10.0 out of 10, Exceptional, (3)
"Amazing place with plenty of room for the entire family! Our hosts were wonderful and answered all the questions and concerns we had! The host made sure we had all the amenities and more, had a wonderful pool, game room, fire pit, plenty of space for everyone! We will be back! "
United States
Jill S.
The price is AU$1,616
includes taxes & fees
20 Oct - 21 Oct
Indoor pool with 4-bedrooms in charming Goshen with WiFi and so many extras
Book your Fall Getaway now ! Our Season ends November 22!
10.0 out of 10, Exceptional, (4)
"Absolutely wonderful property and hosts…. Will definitely stay again. "
United States
cindy b.
Book your Fall Getaway now ! Our Season ends November 22!
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

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 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?

NEW Spacious Lakehouse Retreat +private pier: 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 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Leesburg?

With 11 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.