Holiday Homes in Leesburg

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Featured Holiday Homes in Leesburg and around

⚓️Direct lake view with available Tritoon boat rental
Fridge, microwave, oven, stovetop
⚓️Direct lake view with available Tritoon boat rental
9.8 out of 10, Exceptional, (7)
"The house was better than we expected. It had everything we needed. Communication with owner was good! Neighbors were lovely. Would stay again. "
⚓️Direct lake view with available Tritoon boat rental
Charming 3-bedroom lake house on Tri lakes 6 miles north of Columbia City.
Exterior
Charming 3-bedroom lake house on Tri lakes 6 miles north of Columbia City.
10.0 out of 10, Exceptional, (1)
"Had a great time. Host was very communicative. Will book again. "
Charming 3-bedroom lake house on Tri lakes 6 miles north of Columbia City.
Charming farmhouse in peaceful countryside
Pool
Charming farmhouse in peaceful countryside
10.0 out of 10, Exceptional, (127)
"Beautiful little house in the country. Have stayed multiple times and is excellent every time!!"
Charming farmhouse in peaceful countryside
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
Fridge, microwave, stovetop, coffee/tea maker
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
9.4 out of 10, Exceptional, (21)
"So thankful to Lyndon & family who went the extra mile for us when we needed a place to stay in Goshen while having rv repaired at Affinity! We loved this adorable farm house that had absolutely everything we needed!! And we all loved their blue heeler pup - Sophie!! Would stay here again! Beds so comfy, kitchen so functional (we cooked daily) and having the washer & cryer was an added bonus!! "
Cozy Goshen Farmhouse ~ 9 Mi to Amish Acres
The Old Stone Cottage at Tippy
Exterior
The Old Stone Cottage at Tippy
10.0 out of 10, Exceptional, (8)
"My family and I were impressed with how well the cottage is maintained as well as how welcoming the hosts are. Kent was extremely responsive and addressed our questions relating to the area and property promptly. Swimming on the lake was beautiful, relaxing, refreshing, and rejuvenating. We didn’t have to leave except for groceries as all our needs were met including board games, grill, water accessories, and lots of other amenities. I highly recommend this beautiful and well-maintained property...
The price is €467
includes taxes & fees
29 Sept - 30 Sept
The Old Stone Cottage at Tippy
Trail Side in the Heart of Winona Lake
Exterior
Trail Side in the Heart of Winona Lake
10.0 out of 10, Exceptional, (10)
"My husband and I very much enjoyed our stay. The home was peaceful, comfortable and clean. We loved the front porch and the propane fire pit there. The proximity to the trails, lake and shoppes made it easy for us to take advantage of all of them. It was everything we wanted. "
The price is €234
includes taxes & fees
3 Oct - 4 Oct
Trail Side in the Heart of Winona Lake
Lakeside Indiana Vacation Rental Near Fort Wayne!
Fridge, microwave, stovetop, dishwasher
Lakeside Indiana Vacation Rental Near Fort Wayne!
10.0 out of 10, Exceptional, (10)
"It was not a disappointment"
Lakeside Indiana Vacation Rental Near Fort Wayne!
Waters Edge Cottage on Big Barbee Lake!
Exterior
Waters Edge Cottage on Big Barbee Lake!
10.0 out of 10, Exceptional, (14)
"The cottage was great"
Waters Edge Cottage on Big Barbee Lake!
Winona Lake Cottage w/Deck
Terrace/patio
Winona Lake Cottage w/Deck
10.0 out of 10, Exceptional, (37)
"Me, my wife, and our dog enjoyed our stay at the Winona Lake Cottage. The home was in great condition and was very clean. The deck is a wonderful spot to sit and relax. "
The price is €227
includes taxes & fees
30 Sept - 1 Oct
Winona Lake Cottage w/Deck
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP
Property grounds
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP
8.6 out of 10, Excellent, (18)
"The neighborhood was nice. The different levels of the house were good for accomodating our family. A few minor repairs were needed. We didnt use the hot tub due to lots of spiders all over it. The property manager helped us locate enough life vests, and was very helpful. Overall we really enjoyed our stay. "
Spacious FiveStar Lakefront Retreat-4BR/4BA w/HotTub,GameRoom, FirePit, SUP
Lake Wawasee Escape: private pool, hot tub, pier, kayaks & paddleboat!!!
Outdoor pool, a heated pool
Lake Wawasee Escape: private pool, hot tub, pier, kayaks & paddleboat!!!
10.0 out of 10, Exceptional, (14)
"Loved the house, pool and hot tub. Would stay there again."
Lake Wawasee Escape: private pool, hot tub, pier, kayaks & paddleboat!!!
Lakefront Syracuse Home w/ Deck & Private Dock!
Fridge, microwave, stovetop, dishwasher
Lakefront Syracuse Home w/ Deck & Private Dock!
9.8 out of 10, Exceptional, (7)
"Place was perfect for a family reunion. Right on the water"
Lakefront Syracuse Home w/ Deck & Private Dock!
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
Fridge, oven, stovetop, coffee/tea maker
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
9.4 out of 10, Exceptional, (23)
"I spent every summer of my childhood in Oakwood, so I know the cottage well. It used to belong to Rev. Ross Cook. My grandparents were George and Marie Cook (no relation to Rev. Cook) and they built the cottage at 1019 S Lake Dr. They worked at the old hotel every summer for decades. My dad also worked there during his teen years and so did I. I loved the view of the park. I spent so many happy hours there as a kid, and my granddaughters had just as much fun as I ever did. So, I am not your...
Beautiful cozy cottage 1 block from the lake and Oakwood hotel.
The Heron House @Waldron Lake
Property grounds
The Heron House @Waldron Lake
9.8 out of 10, Exceptional, (25)
"Great house, lots of beds, right on water! Perfect spot to hang with a big group of people for a lake weekend. House is clean, well-stocked and the outside area is the highlight! Would definitely stay again. The host is really responsive and helpful as well."
The price is €679
includes taxes & fees
29 Sept - 30 Sept
The Heron House @Waldron Lake
`Burning Pine Inn' Farm House in Amish country.
Interior
`Burning Pine Inn' Farm House in Amish country.
10.0 out of 10, Exceptional, (13)
"This lovely, immaculate, spacious home provided a wonderful gathering place for our family. We traveled from NY and VA to Goshen, IN to celebrate the wedding of my nephew. The place was perfect for all ages including my 88 yo mother to 5 yo twins. We enjoyed sitting on the back porch, games of basketball, two new kittens, napping in the hammock and hearing the horse and buggies. The host was very responsive. We will plan to stay here again on our next trip to Goshen. Thank you for sharing...
`Burning Pine Inn' Farm House in Amish country.
Adorable Wawasee Cottage in Oakwood Park
Property grounds
Adorable Wawasee Cottage in Oakwood Park
10.0 out of 10, Exceptional, (7)
"Very good. Very clean, well stocked, open floor plan. Small bedrooms and 1 small bath, but it worked for us. Very good experience. "
The price is €475
includes taxes & fees
30 Sept - 1 Oct
Adorable Wawasee Cottage in Oakwood Park
Eagle's View Indiana waterfront home on a premier fishing lake pontoon included!
View from property
Eagle's View Indiana waterfront home on a premier fishing lake pontoon included!
10.0 out of 10, Exceptional, (13)
"I've stayed in a lot of VRBO'S and this property was the cleanest. Beautiful view of the lake and it was nice to be able to use the pontoon. Very peaceful and quiet. Neighbors were very friendly as well. "
Eagle's View Indiana waterfront home on a premier fishing lake pontoon included!
GORGEOUS!!! Open concept renovation. Wawasee, Oakwood Park water front!
Dining
GORGEOUS!!! Open concept renovation. Wawasee, Oakwood Park water front!
9.2 out of 10, Wonderful, (31)
"The house was beautiful -- totally up to date, had everything we needed and more, open floorplan was perfect for our group when cooking and hanging out, back yard was peaceful backing up to water in a "cul-de-sac", location was convenient to stores/restaurants, lake was very nice for our boating (tubing, waterskiing), host was very accommodating and responsive when I had questions. We definitely will be back!"
GORGEOUS!!! Open concept renovation. Wawasee, Oakwood Park water front!
Stunning lakefront log cabin on a private acre
Pool
Stunning lakefront log cabin on a private acre
9.6 out of 10, Exceptional, (40)
"We absolutely LOVED the Mavis lodge!! Incredibly cozy, AMAZING location, large yard ( hard to find on Wawasee!) and very flat lot. We will definitely be back...I teared up a bit when we had to leave."
Stunning lakefront log cabin on a private acre
Notre Dame Home games / Experience Lakefront Life
Notre Dame Home games / Experience Lakefront Life
10.0 out of 10, Exceptional, (35)
"Cute, updated cottage. Everything we needed for 2 adults and a few nephews. So clean, and well stocked. Excellent, attentive hosts. Wonderful screened porch close to the lake. Lovely view. Plenty of toys for fun at the lake. Would definitely rent this place again."
Notre Dame Home games / Experience Lakefront Life
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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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Other property types in Leesburg

Beautiful lakefront property
Fridge, microwave, oven, stovetop
Beautiful lakefront property
10.0 out of 10, Exceptional, (25)
"Everything was perfect! There were no details left out in this home. It had everything you could imagine in a home and then some. Warm and cozy feel and nicely decorated! Would definitely stay here again😊"
Beautiful lakefront property
The Old Stone Cottage at Tippy
Exterior
The Old Stone Cottage at Tippy
10.0 out of 10, Exceptional, (8)
"My family and I were impressed with how well the cottage is maintained as well as how welcoming the hosts are. Kent was extremely responsive and addressed our questions relating to the area and property promptly. Swimming on the lake was beautiful, relaxing, refreshing, and rejuvenating. We didn’t have to leave except for groceries as all our needs were met including board games, grill, water accessories, and lots of other amenities. I highly recommend this beautiful and well-maintained property...
The price is €467
includes taxes & fees
29 Sept - 30 Sept
The Old Stone Cottage at Tippy
beautiful cottage by the lake. Relax and enjoy your stay.
Fridge, microwave, oven, stovetop
beautiful cottage by the lake. Relax and enjoy your stay.
10.0 out of 10, Exceptional, (17)
"Very clean, very nice location. Had all the amenities we needed for a very relaxing and comfortable stay. "
beautiful cottage by the lake. Relax and enjoy your stay.
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.