Holiday rentals in Diamond Island

-The District 5 Schoolhouse-

The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

FARM 10 acres, pond, Hot tub, king bed 30 min ND

Come to the farm for peace, quiet, nature walks, bird watching, and fishing in the spring-fed 3-acre pond and find a new sense of calm. All you need is to build a fire, then sit back and relax. Winter or summer, the farm offers 10 acres of space to run around with your pups or bags, frisbee, and even a bit of golf. Kayak or canoe, too! So many wineries, bike trails, and parks are close by. End your day with a relaxing, stargazing hot tub overlooking the pond. Enjoy! 10 min east of Three Oaks.

The Hideaway on Mitchellii Lane

A completely furnished apartment in the basement of our log home (our main residence) on 5 acres of woods above beautiful Shavehead Lake. Entrance into the apartment through a screened in porch and double French doors provides privacy and space to relax and enjoy the beautiful outdoor landscape. A large egress window allows natural sunlight into the bedroom on the opposite side of the wall from the kitchen/dining room/living room. High speed internet & YouTubeTV provide entertainment options.

Lux, Hot Tub, Restore, Calm, Creekside, Escape

*Escape to your private couple’s retreat. *Whether sipping coffee at sunrise or star gazing, The Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug to reconnect

Private Lake+Fire Pit+Sauna+Kayaks | Pine & Paddle

Welcome to Pine and Paddle — the perfect place to unplug, recharge, and reconnect with nature by the lake. Unwind at this cozy lakeside tiny home, perfect for couples, friends, or solo travelers seeking peace, nature, and a hint of adventure near downtown Shipshewana. 🔥 Campfire pad w/ firewood + lake views 🛶 Kayaks + fishing poles + private dock ♨️ Wooden barrel sauna for ultimate relaxation 🌳 Private lake, beach, & outdoor games 🛏️ Sleeps 5 w/ full-size bunks + couch

Hidden Country Hide-A-Way

Come relax in our cozy, modern country, studio apartment. It is  equipt with a fully stocked kitchenette, private bathroom, comfortable living space, large screen tv and office work space.  Enjoy some of the most picturesque landscape Northern Indiana has to offer.  We are just a 10 min walk from Stone Lake and have kayak rentals available upon request.  We are conveniently located 8 miles from Shipshewana and Middlebury, IN and just a 40 minute drive from Notre Dame.

Quiet cottage on Buck Lake, 1 bedroom

Take it easy at this unique and tranquil getaway at Hummingbird Hill Cottage!You’ll be on peaceful and beautiful, no-wake Buck lake where you can enjoy kayaking, paddleboarding, fishing, and more! Take a hike, ride bikes, or play disc golf in the beautiful Dr. Lawless International Dark Sky Park which is directly across the street! Whether you’re looking to have a couples getaway, a guys’ fishing trip or time with girlfriends, Hummingbird Hill is for you!

Cozy cottage for two with hot tub!

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with sheep roaming the pasture. We also have a couple cats that claim the pool area as their own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.

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.

Little House On The River

Escape to the Little House On The River in Elkhart, IN! This cozy 1-bedroom, 1-bath retreat sleeps 4 and offers stunning river views, a private deck, and all the comforts of home. Just 30 minutes from Notre Dame and a short drive to Shipshewana, it’s the perfect spot for game days, Amish country exploring, or simply relaxing by the water. Peaceful, private, and unforgettable—your riverside getaway awaits!

Outpost Treehouse

The lookout inspired Outpost Treehouse (not actually attached to a tree) sits in a white pine forest in the middle of a 50 acre active farm. The 15 hand crafted windows allow for great views watching out for Michigan wildlife--White tail deer, turkeys, owls, coyote have all been spotted from the elevated wrap around deck. The biggest regret that guests have noted is “we wish we would have stayed longer”!

Rainbows End 🌈 Bourgeois

Escape to a pet-friendly cottage in the Midwest. Nestled amidst scenic trails, with access to the South Branch of Galien River. Relax in the whirlpool tub, explore nature, and create cherished memories. Fully equipped kitchen, washer/dryer, and inviting ambiance. 10 mins from Lake Michigan, 3 miles from Fourwinds Casino. Experience rural bliss in this delightful cottage.