Holiday houses in Leland Township

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!

Two Fish Stay, Downtown, Overlooking Lake Michigan

Two Fish Stay is located in downtown Leland, just steps away from historic Fishtown, Leland harbor and beaches. The space offers beautiful sunset views of Lake Michigan and the Manitou Islands. Leland was chosen the second ‘Best Place to Watch a Sunset’ in North America by USA TODAY in 2013. Two Fish Stay is a charming 1400 sq. ft. walk-up above a thriving retail business, in a historic building. Fishtown is a well-preserved collection of 19th-century fishing shanties, smokehouses and fish tugs.

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!

New A-Frame in wine country

Welcome to Owl Ridge A-Frame! This NEW cabin sits on 8 wooded acres and features a modern, comfortable design with custom finishes. The large, open concept gathering space has room for your whole group to be together. Enjoy a fire pit, outdoor dining and acres of rugged woods to explore. Within 4 miles of 5 wineries. 5 minutes to Lake Leelanau, 7 minutes to Suttons Bay, 12 minutes to Leland and 30 minutes to Traverse City. Enjoy beaches, hiking, dining, shopping and endless Leelanau charm.

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.

The Round Haven with Big Glen Lake Access

Experience living in the round. This recently renovated home is a super energy efficient 30 ft diameter circle. We are situated in the heart of Sleeping Bear National Lakeshore and a 300 ft walk to a secluded public access on Big Glen Lake. A place to adventure, relax and restore: this home is designed for sustainability and comfort. The perfect home base to explore the wonder of Sleeping Bear and surrounding quaint towns. We hope you find inspiration and rejuvenation.

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.

Luxury Couples Retreat W/Hot Tub in Traverse City!

Escape to Rise Retreat, a newly renovated luxury tiny cabin on 6 private acres just 18-minutes from downtown Traverse City. Unwind in the hot tub under the stars, explore nearby trails, or cozy up by the fire. Designed for couples or small groups, this peaceful hideaway blends rustic charm with modern comfort. Featuring a full kitchen, two queen beds, and thoughtful details throughout. Your perfect Up North getaway starts here.

Romantic Glacier Hot Tub Hideout | A-Frame

Nestled on the Betsie River near Crystal Mountain, this romantic A-Frame offers a private hot tub under starry skies, a glowing indoor fireplace, and a loft bedroom overlooking the river. Sip local coffee from the espresso bar, fish from the riverbank, or unwind by the firepit. Designed for couples yet comfortable for small families seeking a peaceful riverfront escape. Weekend dates go fast — book early to secure your stay.