Holiday houses in Glen Arbor

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Top-rated holiday rentals in Glen Arbor

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Top Guest favourite

Tiny home in Lake Ann

5 out of 5 average rating, 230 reviews

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!

Superhost

Home in Empire

4.88 out of 5 average rating, 208 reviews

Lone Pine Cottage on Little Glen Lake

Two bedroom vacation home/cottage located on Little Glen Lake. Nicely updated space with brand new bathroom and flooring throughout. Home has DirecTV, wifi, and gorgeous views of one of the most beautiful lakes in America. 100 feet of private sandy frontage with dock. Comfortable patio seating on the deck overlooking the lake. Guests are welcome to use the two kayaks and canoe. Fire pit located by the shore. Across the street from Sleeping Bear Dunes National Lakeshore and its endless trails.

Guest favourite

Chalet in Glen Arbor

4.92 out of 5 average rating, 131 reviews

Clarity House, Downtown Glen Arbor

Walking distance to all Glen Arbor has to offer! 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 feels nearly hidden in the woods, despite being in the center of town! Find us on “the Gram” under Clarity_Guest_House.

Guest favourite

Cabin in Maple City

4.88 out of 5 average rating, 262 reviews

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.

Top Guest favourite

Cottage in Northport

5 out of 5 average rating, 292 reviews

The Granary Northport . Rustic Modern Seclusion

Summer dates opening up mid February! 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 2. Absolutely no cats are allowed. We do not have a TV, but we do have fiber optic high speed internet.

Guest favourite

Cabin in Glen Arbor

4.97 out of 5 average rating, 147 reviews

Glen Arbor-theater/pool table/arcade-walk to town

Glen Arbor, MI | Sleeps 8 | 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.

Guest favourite

Cottage in Maple City

4.93 out of 5 average rating, 118 reviews

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.

Top Guest favourite

Dome in Glen Arbor

5 out of 5 average rating, 230 reviews

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.

Top Guest favourite

Guest suite in Glen Arbor

4.97 out of 5 average rating, 130 reviews

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!

Guest favourite

Home in Thompsonville

4.94 out of 5 average rating, 146 reviews

Romantic Hot Tub Hideout | A-Frame

Dreamy A-Frame Near Crystal Mountain Escape to a cozy A-frame tucked in a wooded retreat near Crystal Mountain Resort. Soak in the private hot tub, relax by the fireplace, or unwind around the fire pit under the stars. Enjoy riverfront views, a fully equipped kitchen, and endless outdoor fun—skiing, snowmobiling, hiking, fishing, and more. ✨ 2BR | 2BA | Hot Tub | Fire Pit | River Views Book now for a magical Michigan getaway!

Guest favourite

Cottage in Glen Arbor

4.97 out of 5 average rating, 132 reviews

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.

Guest favourite

Cottage in Cedar

4.93 out of 5 average rating, 107 reviews

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.