Family-friendly holiday rentals in Leelanau Township

Cozy Aframe on Tunnel of Trees Harbor Springs

Cozy A-frame perfectly located minutes from downtown Harbor Springs. Nestled in the trees across from a nature preserve so you get that “cabin-in-the-woods” feel while being close to everything the area has to offer. Perfect homebase for “Up North” adventuring: •5 min from downtown Harbor Springs •20 min from Petoskey •40 min to Mackinaw •10 min to Nubs Nob/Highlands •5 min to Tunnel of Trees M-119 Home Features: •2 bdrms w queen beds •Indoor & Outdoor firepit •Stocked kitchen •Front/back deck

The Underwood Tiny House - with private hotub

Fall into the rabbit hole to experience our unique twist on a Wonderland inspired tiny house. Boasting a Queen size bed, a full kitchen and bathroom, and everything in between, you are bound to have a relaxing getaway... with a little bit of adventure! The spacious deck (with hot tub) overlooks the forest, and it is the perfect place to enjoy a cup of coffee or a glass of wine. The Underwood Tiny House has been created to give each person who walks through its door an experience like none other!

Organic Vineyard and Farm Oasis

Stay on Leelanau’s only organic vineyard and farm (Green Bird Organic Cellars). This one-of-a-kind stay puts you close to everything in Northport & Leland, while enjoying the natural beauty of our boutique winery. The space has a private entrance, a lofted bed with a ladder(best for folks with full-mobility), a living/dining area, a fridge/microwave/keurig and a full bathroom with a shower. Please note: we are not hosting any farm interns 2026, so the property will be all yours after-hours :)

The "Cherry Cottage", A Vintage Barn Conversion

Brand new custom construction! Nestled on a historic family farm, the Cherry Cottage is a one-of-a-kind, newly converted barn, fusing vintage charm with clean, modern amenities. Two private bedrooms surround a double-height living space, a spacious full bathroom, and a kitchen. Guests are immersed in the beauty of the Leelanau Peninsula and can enjoy the park-like setting of the cottage. Leland, Lake Leelanau, numerous wineries, beaches, hiking and so much more are just a 5-minute drive away!

Leelanau Secluded Tiny House Northport

Newly built tiny house 2 miles south of Northport. Nestled in the woods overlooking a pond and surrounded by an organic vineyard/farm. Short walk to organic winery, 5 min drive to Northport, 15 min to Leland, and 20 min to Sutton’s Bay. Many beautiful beaches close by! Sleeps 4 total, 2 on a queen sized bed in loft and 2 on a futon on main floor. There is running water inside, hot & cold, but there is not a toilet or shower inside. Outside is a very clean portable restroom and outdoor shower.

Rustic Cabin Lakeview

Rustic cabin in view of Toad Lake for your glamping pleasure. Kitchenette, claw foot tub, queen-sized bed, comfy couch, movies to choose from, games and puzzles, clean outhouse. Lake fishing, canoe, kayaks. Get away from it all. Perfect centralized location, amazing stargazing and birdwatching. Easy trip to Charlevoix, Petoskey, East Jordan, Boyne City, Torch Lake, Lake Michigan. One hour to Mackinac Island Ferry. No pets. Smoking outside only. Also see The Loon at Brigadoon listing!

Joe’s Sunset Cabin/ Glamping experience

Come on in Glamping enthusiast, make yourself at home in our small but adorable 12 by 24 rustic mini cabin. Solar powered lights and electric plug-ins and lights with gas stove and fridge. Queen size futon on main floor , Hot shower outside under the beautiful sky and no more Porta potty located outside. Toilet is now inside! Surrounded by a beautiful hardwood forest. Be one with nature. Sitting just up the hill from our mini donkeys and our 4 adorable boy alpacas.

The Granary Northport . Rustic Modern Seclusion

Voted one of the top 85 Airbnbs by Conde Nast Traveler. The Granary is a lovingly restored two bed + one bath cabin located on 12 wooded acres with a secluded Lake Michigan beach nearby. A short drive to town will give you access to restaurants, groceries, breweries and wineries. Dogs are welcome! Please message us to discuss bringing more than 1. Absolutely no cats or other pets are allowed. We do not have a TV, but we do have fiber optic high speed internet.

Sommer's Retreat

Sommer's Retreat is a year round northwoods cabin nestled in the pines and surrounded by a 300 acre nature preserve. Our location is a short distance from the Jordan River Valley and within 20 minutes of the south arm of Lake Charlevoix, Torch Lake, Lake Michigan, Shanty Creek Schuss Mountain Resorts, Glacial Hills, orchards and farm markets. The cabin is a spacious two story retreat that will sleep 6 in two bedrooms and a loft. Guests have access to cabin wifi.

Cherrywood Cottage

Cherrywood Cottage is a true "Up North" retreat within walking distance to the Village of Northport. 2 bedrooms (queen in each) and sleeper sofa in living room. Inside beautiful knotty pine walls and ceilings; gas fireplace, full kitchen. Outside a large patio overlooking the woods with gas grille. Barrier free. Cherrywood and its sister cabin, Applewood, are attached properties. Rent both for a larger event! They are part of the Homewood Cottage Association.

Cozy, Rustic Little Cottage in the Woods

Cozy, rustic tiny cottage in the woods is located about 6 miles (10 minutes) North of Suttons Bay town center and 9 miles (15 minutes) South of Northport. Downtown Traverse City is 22 miles or (35 minute) drive. Location is close to many beaches, restaurants, wineries, microbreweries, and Sleeping Bear Dunes National Lakeshore. It is a great place for couples seeking a quiet romantic getaway or a single outdoor adventurer.

Northport Fall Getaway with Privacy

Come visit the Leelanau Penninsula and stay in a quiet Northport home off of M22. Private location with 20 acres of natural beauty. All bedding and furniture are new. Located in close proximity to several vineyards and beaches including Lake Michigan and Grand Traverse Bay. Enjoy camping or a small bonfire in the backyard or visit Northport just a mile away. Great for families or large groups.