Family-friendly holiday rentals in Glen Arbor 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!

Grandpa's Little Cabin-Across Big Glen

Stay at our classic, tiny log cabin from the 1940s. Originally the front office for the log cabin retreats on Glen Lake, more recently this was 'Grandpa's Little Cabin', providing decades of family memories. Located across from Old Settler's Park, it is situated in a beautiful, woodsy surrounding, with the benefits of the park's dock access and sunset views. Located just a short drive from Glen Arbor, The Dunes and all that Leelanau offers. Come see Up North as it was originally intended.

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.

Empire Blue House w/ Hot Tub

Clean, new home (in 2020) with 6-person hot tub is less than a 4-minute walk to Lake Michigan, and 3-minutes to downtown Empire. In the heart of Sleeping Bear Dunes National Lakeshore and its amazing trails, there is over 1400 square feet of indoor living space, plus 1000 sq feet of covered decks. The location offers easy access to a variety of outdoor recreation, Leelanau Wineries, and is 25 miles to Traverse City shopping and nightlife or 25 miles to Crystal Mountain Skiing!

Glen Arbor-walk to town - NOW available 6/26-7/3!

Glen Arbor, MI | Walk to Town | Theater Room | Pool Table | Fire Pit | No Pets Located just ½ mile from Lake Michigan and 2 blocks from downtown Glen Arbor, Bear Haven is a warm, inviting home nestled near Sleeping Bear Dunes—named Good Morning America’s “Most Beautiful Place in America.” This three-level getaway blends modern comfort with rustic charm, featuring a white pine interior, custom log furniture, and all the amenities your group needs for an unforgettable stay.

Sleeping Bear Stunner - private, gorgeous views

Welcome to Blue Kettle Cottage. Updated home on 4 acres of private land adjacent to 480 acres of Sleeping Bear Dunes National Lakeshore land. Close to Glen Arbor and Empire. Two generous bedrooms, one bathroom, outdoor shower, beautiful patio with couch and table and fire pit area. The Kettles Trail is your backyard and accessible all year long for hiking, snowshoeing and cross-country skiing. If you are bringing a dog, please read the pet rules and rates before booking.

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.

Clarity House, Downtown Glen Arbor, Hot Tub

Hidden in the heart of Glen Arbor, Clarity House is a modern chalet cabin with 3 bedrooms & 3 full baths; dramatic open concept kitchen/great room; Polished concrete floors (with in-floor heat); large island is central gathering spot with focal points to oversized south/east/west-facing windows for max daylight; 24ft ceiling; stylish design and furnishings. Peaceful outdoor patio with fire pit and hot tub feels “in the woods”, despite being in the center of town!

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.

West Harbor Hideaway

This cozy, one bedroom cottage with modern farmhouse design sits on a nicely wooded and private lot just 1/4 mile west of Glen Arbor. Convenient walking or biking access to all of town's shops and restaurants as well as the beach and Heritage Bike Trail. In the heart of the Sleeping Bear Dunes National Lakeshore, this is the perfect starting off spot for you to enjoy all the beauty Leelanau County has to offer.

Cozy Good Harbor Cottage with hot tub & fireplace

Welcome to our thoughtfully designed 1940's cottage in the woods just minutes from Good Harbor Beach. This quiet retreat gives you access to the wine, food, and nature the Leelanau Peninsula is known for. Enjoy the outdoor fire pit, charcoal grill, fast wifi, Smart TV, and well-appointed kitchen. Sound travels so please be respectful of our neighbors. Sorry, no parties or events. All are welcome.