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
A log cabin with a welcoming front porch is surrounded by lush greenery. A gravel driveway leads up to the cabin, which features large windows and a rustic design. Natural light filters through the trees, enhancing the serene outdoor setting.
Cabin in North Webster
4.89 out of 5 average rating, 216 reviews

Dock of the Bay Fishing Cabin with Boat Dock

"Livin Easy" is close to town, creating the perfect space to have access to peace & quiet while being close to town & water. This cabin is on a private property that guests will have all to themselves while they are here. You will have access to a full kitchen, living room, private bathroom, and a loft which has two beds. This cabin comes w/channel dock space on the S. side of Lake Webster. There is space for your boat & water toys to bring along with you or you to rent @ a marina while here.

Superhost
A firepit area is set on a green lawn, surrounded by four chairs arranged in a circle. In the background, the calm lake reflects the blue sky with fluffy white clouds, while a dock and a kayak can be seen along the shore.
Home in Leesburg
4.88 out of 5 average rating, 17 reviews

Lakehouse, kayaks, dock, fishing, fence for pets!

Beautiful lakefront home on the Barbee chain of lakes. Small, but all you need!! This guesthouse features a kitchen, family room, firepit, dock for your boat, and a fenced in side yard for your dogs!! We supply 2 kayaks with lifejackets and a grill. King size bed in the bedroom! We have a loft for the kids that they will love!!! This house has the best views and best fishing on the chain! Must be 21 to book and show ID after booking confirmation. Plenty of parking. Come make some memories!!

Top guest favorite
A cozy sleeping area features a plush queen bed, adorned with decorative pillows. Natural light streams through skylights, illuminating the space. A wooden dresser adds warmth, while a dreamcatcher hangs on the wall, complementing the tasteful decor and providing a relaxing atmosphere.
Apartment in Warsaw
4.97 out of 5 average rating, 372 reviews

The Loft: 1880

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.

Top guest favorite
Cabin in Warsaw
4.97 out of 5 average rating, 157 reviews

Romantic A-frame · HeartJacuzzi · Firepit · Kayaks

Peaceful channel-front A-frame cabin on Barbee Chain of 7 lakes! This cozy retreat features a charming, rustic interior, fully stocked kitchen, and heart-shaped jacuzzi. You'll love stargazing or drinking morning coffee on your spacious deck with gas firepit and gas grill. Unwind by the cozy fireplace, kayak and fish on the Barbee Chain of 7 lakes, and make s’mores by the waterside firepit! Minutes from boat launch. Book now for unforgettable memories in this intimate, picturesque getaway!

Guest favorite
A fire pit surrounded by several chairs is set on a grassy area, providing a cozy gathering spot. A lake view is visible in the background, with docks and boats. A vibrant sunset sky adds color, while a kayak is propped against a tree nearby.
Home in Warsaw
4.89 out of 5 average rating, 28 reviews

Little Barbee Lakefront Bungalow

Step into a simpler time at our cozy, lakefront cottage on Little Barbee, where time slows down and relaxation takes over. Whether escaping with family or friends, immerse yourself in the joys of lakeside living. Engage in outdoor games, sizzle up a feast on the grill, and drink in the gorgeous waterfront views and spectacular sunsets. With your own private dock, there's space to moor your boat for aquatic adventures. Complete your perfect day with a crackling bonfire at the water's edge.

Top guest favorite
A collage showcasing the lakefront view at sunset, highlighting calm waters and distant docks. An interior view features a well-lit living area with comfortable seating and a dining table, alongside cozy bedding and decorative accents, providing a sense of warmth and relaxation.
Cottage in Warsaw
4.93 out of 5 average rating, 96 reviews

Lake Front + Private Pier + Fire Pit + Kayaks

We invite you to come enjoy your time away at our delightful summer lake front cottage on Little Barbee Lake. Close proximity to Big Barbee Lake (all sports lake) Little Barbee is part of the Barbee Chain of Lakes with plenty of room to boat and fish. Bring your own boat or jet ski as the dock is steps away from the cottage. ••• Sunday AND Holiday check-ins may be available depending on our cleaning schedule! Please contact me and we'll do our very best to accommodate your schedule!

Guest favorite
Guesthouse in Leesburg
4.96 out of 5 average rating, 24 reviews

Tippy Lake Retreat | Kayaks, Bonfires & Lake Views

UNIQUE, SPACIOUS, and HAS IT ALL! Views and Sunsets of Lake Tippecanoe - All Sports Lake; second to none! Space to sleep a minimum of 12, 2 full baths with private w/c, walk-in showers, a gas fireplace, amazing 1940's Century boat island, lake access and pier use just steps away, pier space for personal watercraft boat rentals available, please ask for promo code! Kayaks, paddle boards, reverse osmosis water, charcoal grill, outdoor seating, fire pit, artificial grass area, and more!

Guest favorite
A peaceful waterfront view features calm waters reflecting surrounding greenery. A wooden pier extends into the water, bordered by grassy areas. Various boats are visible in the distance, adding to the serene atmosphere of the lake access area.
Home in Warsaw
4.93 out of 5 average rating, 57 reviews

The Little Barbee Lodge *Lake Access*

Welcome to a cozy getaway, The Little Barbee Lodge. Our 2 bedroom, 1 bath cottage is located off the channel *lake access* of Little Barbee Lake! Equipped with the things you need for a relaxing vacation. Watch the sunrise on the screened-in patio. Enjoy the water and the land with our 2 kayak's & 2 adult bikes! In the evening, enjoy a bonfire. *The Barbee Chain of Lakes are noted for the fishing/hunting. I have pier space available for an additional charge. Bring your boat!

Guest favorite
Cabin in Nappanee
5 out of 5 average rating, 6 reviews

The Retreat at Cabin Creek Farms

Escape to our peaceful country cabin nestled down a quiet lane surrounded by rolling farmland and grazing cows. Enjoy spacious accommodations with a wrap-around patio perfect for morning coffee, cozy evenings by the indoor fireplace, and scenic hiking trails right at your doorstep. Your perfect rural getaway awaits! Small events for up to 30 people are allowed upon request before with an extra fee, if interested in hosting an event please request before making the reservation!

Guest favorite
The charming cottage is nestled among trees, featuring a metal roof and wooden exterior. A small covered porch with sheer curtains surrounds the hot tub, while a pergola with string lights stands nearby, accompanied by adirondack chairs and a neatly arranged firewood stack.
Cottage in Goshen
4.94 out of 5 average rating, 594 reviews

Cottage Escape cozy getaway for two, Clean, Quiet

This charming, semi-private cottage, set in a quiet country location is perfect for your next getaway. Small kitchenette with sink, fridge and microwave provides you with kitchen basics. PLEASE NOTE: there is no stove/oven in this room. Bathroom is equipped with all the necessities plus extras like a two person shower with rain fall shower head. Outside is a 2-3 person hot tub along with a beautiful pergola with string lights and adirondack chairs.

Top guest favorite
A sandy lakefront area is visible, featuring several brown Adirondack chairs arranged in a circle around a fire pit. In the background, a wooden dock leads to a covered boat lift, with calm waters reflecting the clouds above.
Cottage in Warsaw
4.96 out of 5 average rating, 272 reviews

Lakewood Cottage on Winona Lake

Modern and light filled lakefront cottage on beautiful Winona Lake. Great views from the lakefront dining area. You walk in the front door and you feel surrounded by the water. Quiet neighborhood is great for biking and walks. You can access the Greenway trail a mile away which takes you to the Village of Winona. Check out our custom video on youtube, just copy and paste the below code into the youtube search bar. AMErvK41MSo

Top guest favorite
A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.
Cabin in Middlebury
4.99 out of 5 average rating, 444 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.

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