Holiday houses in Leland Township

New! Award-Winning Chameleon House & Hot Tub

Welcome to the one and only award-winning Chameleon House -- a 32-foot-high, 9-level modern-industrial masterpiece designed by San Francisco’s renowned Anderson Anderson Architects. This published, trophy-worthy home is unlike anything else, both an architectural landmark and a living work of art. The innovative translucent polyethylene siding reflects and mimics the surrounding landscape and sky, transforming with the seasons. Inside, warm birch wood panels soften the sleek steel construction.

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!

Dome in Suttons Bay with amazing views!

Amazing Views -- Unique Architecture -- Great Location One of the best views on Leelanau Peninsula. Mini-Dome (guest house) sharing 5+ acre property with Big Dome (main house). Conveniently located near the M-22 scenic route, 1 mile from the bike Trail, and within 4 miles of 6 wineries. The interior was newly renovated in 2019. The Mezzanine has 2 queen beds (shared space). You'll love this unique and romantic escape. 2022 Stats: 3 engagements, 6 Anniversaries, 5 birthdays, 4 pre-weddings

Victoria Valley Chalet

This beautiful home, hosted by myself and my lovely wife Brenda. The home has up north charm and character inside and out. Built in 2019, this home has a covered front porch and a elevated back deck overlooking a yard that will be filled with games, including horseshoes and cornhole. After enjoying what Northern Michigan has to offer, come back to relax and recharge in the privacy of your own home. Have a drink by the bonfire in the back yard, grill out and plan your next days adventures.

Soo House

Soo is a very fun cedar shake cabin on 15 forested acres, surrounded by trails, a loon call from Glen Arbor. This scandi-eclectic, cozy spot is a dappled dirt road away from Port Oneida/Good Harbor Bay Beaches and Pyramid Point. Soo stewards a half-mile of private trails on the property itself and borders 27+ miles of maintained MTB/hike/ski trails via the Palmer Woods and Krumwiede Forest Reserves. Soo is the unique family basecamp for your Sleeping Bear Nat'l Lakeshore adventures!

The Sweetbriar

This beautifully remodeled 100-year-old home was taken down to the studs and is now essentially brand new. The stunning new kitchen features gas cooking and new appliances, perfect for cooking and entertaining. The spacious, brand-new bathroom boasts a luxurious walk-in shower and soaking tub for ultimate relaxation. Smart TVs, high-speed Wi-Fi, and a cozy gas fireplace ensure your comfort. Don’t miss the screened-in porch—it’s the perfect spot to unwind and enjoy the surroundings!

Vineyard Cottage | Barrel Sauna on a Vineyard!

The Vineyard Cottage is a charming 4-bedroom home located in the heart of Leelanau's wine country by Aurora Cellars. This property overlooks estate vineyards, the boutique winery, and beautiful rolling countryside. Enjoy our barrel sauna with panorama views! Aurora Cellars is open year round, so stroll over and have a glass of wine or flight during your stay and enjoy the beautifully manicured property and vineyard trails or explore Leelanau County from this centrally located oasis.

Birch and Cedar Main Cottage (Birch)

Welcome to our tranquil and well-appointed countryside cottage, nestled in the heart of Leelanau County, just minutes away from the region's renowned wineries. Situated on a sprawling 5-acre property, our cottage offers a serene retreat for those seeking relaxation and natural beauty. Conveniently located near Suttons Bay, Leland, and Lake Leelanau, our cottage provides easy access to the area's wineries, making it an ideal getaway for wine enthusiasts and nature lovers alike.

Whispering Pines #3 Leland

Take a break and unwind at this peaceful oasis. Meadow setting surrounded by pines and a hobby farm. You might wake up to a few chickens in the yard, or the horse and ponies being led by to the corral. You will see a beautiful starry sky and if you are lucky the Northern Lights! We are close to many things Leelanau County has to offer. The apartment is about 5 miles to Leland or Lake Leelanau and 7 miles to Suttons Bay. Please note- there is no dishwasher or microwave.

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.

Lincoln Lodge: Secluded~Wineries~Dog Friendly

🌲 Secluded 4-Acre Hardwood Retreat 🐶 Pet-Friendly for Family & Friends 🏞️ Covered Porch with Wildlife Views 🌅 Floor-to-Ceiling Nature Windows 💻 Fast 300 Mbps Wi-Fi Hosted by Catered Stays Rentals, we cater to the ideal guest experience, ensuring your comfort and satisfaction. Enjoy a secluded 4-acre property immersed in nature, perfect for both relaxation and adventure. Explore nearby attractions, unwind, and create lasting memories.

Hillside Bungalow - hot tub, coffee bar, firepit!

Welcome to the Hillside Bungalow - a cozy oasis featuring a hot tub, outdoor deck space, firepit, modern fully-equipped kitchen, and coffee bar with a mid-century modern design. Ideally located to visit any of the 16 wineries within 10 miles, drive to a nearby beach, rent some kayaks, go for a hike, bike nearby trails, and peruse the local charming towns - an overall ideal retreat to explore the Leelanau Peninsula and surrounding areas!