Family-friendly vacation rentals in Glen Arbor

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!

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!

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.

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!

The Little Perch near Big Glen private 2 bedroom

Encircled within beautiful hardwoods & located less than 7 miles from both Glen Arbor and Empire, The Little Perch is only a rock skip away from the Sleeping Bear National Lakeshore & the Crystal River. We hope you'll enjoy the streamlined kitchen, full bathroom, comfortable 2 bedrooms (3 beds), private laundry tower, personal entrance & spacious parking. The Little Perch is a charming and exclusive upper level guest house, conveniently holding up to 4 guests!

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.

Base Camp Beulah—at Crystal Lake

Elevated Escape at Base Camp Beulah—newly renovated modern log cabin with king beds—1 block from pristine Crystal Lake and a quick ride to charming downtown Beulah. Situated on US 31, offering effortless access to Sleeping Bear Dunes, Crystal Mountain (12 min), and beyond. Circular driveway fits boat & snowmobile trailers. Sleeps 9—ideal for two families or friends seeking refined comfort.