Vacation rentals in Leesburg

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Top-rated vacation rentals in Leesburg

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Winona Lake

4.99 out of 5 average rating, 282 reviews

Off The Beaten Pass -on Greenway .3 mi Beach/Park

Charming home nestled on Greenway Trails in historic Winona Lake, IN. Completely renovated in 2017 with cozy living space. Walking/biking distance to Beach, Park, Playground, Splash Pad, Tennis Courts, Basketball Court, Volley Ball Court, The Village shopping & restaurants, Grace College. Beautiful sunsets from the beach! Perfect for couples, solo adventurers, business travelers, small families, mountain bike get-aways, cross-country skiing, weekend tailgating Notre Dame Football games, etc!

Aug 28 – Sep 4

$106 per night
Guest favorite

Guesthouse in Winona Lake

4.99 out of 5 average rating, 193 reviews

Guesthouse Suites (C)

For business or pleasure, you will experience lovely Winona Lake staying in our newly constructed GuestHouse Suites, next to the heart of The Village at Winona. A short walk uphill to Grace College or a short walk over to visit the shops and restaurants, Spring Fountain Park graces your view. Winona Lake Limitless Park, public beach, splash pad, tennis, pickleball and basketball courts, paved walking/bike trails, mountain bike trails, and ice skating pavillion, are all within walking distance.

Jan 3 – 10

$112 per night
Guest favorite

Apartment in Goshen

4.96 out of 5 average rating, 728 reviews

Half-Moon Cottage

Enjoy privacy in this beautifully handcrafted cottage with arched ceilings. The cottage is 2 miles from downtown Goshen - a vibrant small town with restaurants and shops. It's 1 mile from Goshen College, 45 minutes from Notre Dame and 25 minutes from the Amish town of Shipshewana. The cottage is beside a fruit, nut and berry orchard and gardens. It's adjacent to a city bike trail that links to the Pumpkinvine nature/bike trail. It's close to a train crossing (with whistle) and a busy street.

Nov 9 – 16

$72 per night

Popular amenities for Leesburg vacation rentals

Other great vacation rentals in Leesburg

Guest favorite

Cabin in Middlebury

4.99 out of 5 average rating, 189 reviews

Cabin off 39 - Peaceful, private one bedroom cabin

Dec 21 – 28

$141 per night
Guest favorite

Home in Syracuse

4.95 out of 5 average rating, 57 reviews

Mt. Pleasant: Newly renovated with a hilltop view

May 1 – 8

$79 per night
Guest favorite

Home in Winona Lake

4.96 out of 5 average rating, 82 reviews

Short Walk to the Lake and Trails

Nov 9 – 16

$86 per night
Guest favorite

Cottage in Warsaw

4.95 out of 5 average rating, 60 reviews

Barbee Chain Lake Access! 3 Bedroom Cozy Cottage

Jan 26 – Feb 2

$87 per night
Guest favorite

Home in Leesburg

4.87 out of 5 average rating, 31 reviews

SUNNY DAZE with lake views and bonfire evenings!

Oct 10 – 17

$272 per night
Superhost

Home in Warsaw

4.87 out of 5 average rating, 31 reviews

The Green House

Apr 23 – 30

$68 per night
Guest favorite

Cottage in Warsaw

4.92 out of 5 average rating, 38 reviews

Lake Haven Cottage • Warm, Cozy Winter Get Away •

Aug 13 – 20

$131 per night
Guest favorite

Home in Leesburg

4.98 out of 5 average rating, 61 reviews

Endless Summer, a Relaxing Lakeside Retreat

Mar 7 – 14

$231 per night
Guest favorite

Cottage in Leesburg

5.0 out of 5 average rating, 12 reviews

Lookout Point-Lovely cottage Barbee Chain of Lakes

May 30 – Jun 6

$151 per night
Guest favorite

Cottage in Warsaw

4.98 out of 5 average rating, 90 reviews

The Channel House @ Hoffman Lake

Jun 23 – 30

$125 per night
Guest favorite

Home in Nappanee

4.97 out of 5 average rating, 34 reviews

Country Cottage

Oct 28 – Nov 4

$120 per night
Guest favorite

Apartment in Warsaw

4.96 out of 5 average rating, 27 reviews

Downtown Loft with rooftop patio

Oct 19 – 26

$116 per night

Destinations to explore

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  3. Indiana
  4. Kosciusko County
  5. Leesburg