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.

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Guest favorite

Home in Winona Lake

4.99 out of 5 average rating, 287 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!

Sep 10 – 17

G$25,246 GYD per night

Guest favorite

Guesthouse in Winona Lake

4.99 out of 5 average rating, 195 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.

Dec 8 – 15

G$26,874 GYD per night

Guest favorite

Home in Warsaw

4.97 out of 5 average rating, 219 reviews

Lakeveiw Cottage

Welcome to Lakeveiw Cottage, enjoy the public Winona Lake access with everything the lake has to offer, boat, canoe, and paddle board and bike rental available, at Winona Village. Well equipped cottage will comfortably sleep 6. Short Walk or take the many bike paths to the Village of Winona, and Close to Wagon Wheel Theatre and Warsaw where the unique shops and savory restaurants like One Ten Craft Meatery await you. new appliances and three new queen beds. New high speed internet and cable TV

Dec 15 – 22

G$39,338 GYD per night

Guest favorite

Apartment in Goshen

4.96 out of 5 average rating, 740 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.

Mar 9 – 16

G$17,255 GYD per night

Guest favorite

Cottage in North Webster

4.94 out of 5 average rating, 175 reviews

Webster Lakefront Updated Studio with Pier & Deck

Lakefront! Simple, practical, purposeful lakefront cottage with pier. Ideal for those who dream of waking to a lakeview. Enjoy lake/boating activities, playing yard games, fishing along shore/pier, or just unwind while relaxing on the deck watching a sunset. See FAQ in Guest Access section Studio. Stairs. No beach area. No swimming at the pier. No smoking on property. Only registered guests permitted on property, no visitors. Located on the east side of the lake, quiet wooded neighborhood.

Mar 19 – 26

G$31,322 GYD per night

Guest favorite

Apartment in Warsaw

4.96 out of 5 average rating, 289 reviews

The Loft: Heritage House Farmstead

Located near, Zimmer-Biomet, and Cinema. Perfect for business travelers & those visiting family & friends. We've hosted contract workers & parents visiting Grace College students. The Loft is a second-story self-contained annex attached via a private entrance. On-Site Parking. We are situated on 3 acres and love our 1909 farmhouse and The Barn 1880: Historic Venue. Open plan living/dining w/fully equipped kitchen w/coffee bar, separate private queen bedroom & private bathroom. See Reviews.

May 25 – Jun 1

G$31,271 GYD per night

Guest favorite

Cottage in Syracuse

4.95 out of 5 average rating, 119 reviews

Sunny channel front cottage on Lake Wawasee

Huge open concept with plenty of light. Take a .23 mile walk to our private beach, lounge by the pier, or rent a boat and head to the best sand bar in the Midwest. Lake Wawasee is the largest natural lake in Indiana. It offers great skiing and fishing, 3 restaurants you can enjoy by boat and the best sunrise/sunset boat cruises you can imagine. The house is only 5 minutes from either Syracuse or North Webster to check out the local shopping boutiques and farmers markets.

Oct 16 – 23

G$27,670 GYD per night

Guest favorite

Home in Warsaw

4.92 out of 5 average rating, 319 reviews

Renovated Home Near Popular Restaurants & Shops

Welcome to this renovated 3 Bedroom/1 Bathroom home located near major employers, popular restaurants and shops and a short walk to the Village of Winona, Grace College and the hiking/biking trails. The home is ~850 sq ft and offers off street parking, on-site laundry facilities , wi-fi, Netflix, and much more. You can check yourself in and I will be available to answer questions you have via phone. I'm certain you will enjoy this sweet little home and all it has to offer!

Jun 12 – 19

G$26,685 GYD per night

Superhost

Guesthouse in North Webster

4.92 out of 5 average rating, 155 reviews

Come relax near beautiful Lake Webster

Our place is close to Webster Lake beach & boat ramps w/boat rentals. Whether you are looking for a relaxing getaway or to gather with friends & family you’ll love our place because of the location. We are centrally located between South Bend (Notre Dame) and Fort Wayne (Tincaps stadium/ Coliseum), close to many small towns w/ lakes, great eateries, & antique shops. With so much to offer you can find something for everyone or sit back & relax in our relaxed environment.

Aug 11 – 18

G$20,947 GYD per night

Guest favorite

Guesthouse in North Webster

4.98 out of 5 average rating, 207 reviews

Modern Webster Lake cottage

This home has a great floor plan for 2-4 people with a small loft bed for a youngster. It has all the comforts of home, including high end kitchen accessories and in-unit washer and dryer. Softener and reverse osmosis filter for great water. Great maple hardwood floors and a front deck for outdoor barbecuing. Parking for 3 cars right outside and a shed with lots of amenities including bikes and hammock for recreation and relaxing.

Sep 29 – Oct 6

G$18,341 GYD per night

Guest favorite

Cabin in Middlebury

4.99 out of 5 average rating, 200 reviews

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

Dec 9 – 16

G$34,876 GYD per night

Guest favorite

Guest suite in Goshen

4.96 out of 5 average rating, 168 reviews

Colorful Country Apartment

Peaceful get-away in the country. Rich colorful apartment ideal for an extended business trip or just for fun. Five to ten minutes from an eclectic mix of dining options and bustling art/artisan scene in downtown Goshen. Walking/biking trails are 1.5 mi. away. Bike trails are also available in Goshen and extend all the way from Elkhart to Shipshewana. We're two minutes from Goshen Airport.

Jan 3 – 10

G$17,083 GYD per night