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, 224 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!

Guest favourite

Condo in Cedar

4.91 out of 5 average rating, 117 reviews

Golf course view, close to the beach

Efficient condo on the Old Course at Sugarloaf. Updated kitchen, modern furniture (high quality mattress), sleeper sofa, large jetted tub, fast internet, cable, and private patio. 5 min. to Good Harbor Beach, 10 min. to Leland and 30 min. to Traverse City. Easy access to wonderful year round activities. Perfect for a golfing, outdoor adventure or wine tasting trip, or simply a change of scenery for a remote worker. Cross country ski on the golf course, hit the sledding hill across the street!

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.

Guest favourite

Tower in Empire

4.89 out of 5 average rating, 63 reviews

Exodus: Luxury Tower With Hotub Near Sleeping Bear

Welcome to the Exodus Watch Tower, our newest addition offering stunning views and a luxurious space perfect for a getaway in the heart of Empire This home presents a unique and unforgettable experience from the panoramic window view and convenient wet bar, to the wrap-around balcony and relaxing hot tub Despite being the perfect hideaway, you are only: 5 min from Empire Beach 5 min from Sleeping Bear 10 min from Glen Arbor 20 min from Traverse City 30 min from Crystal Mountain

Guest favourite

Chalet in Empire

4.95 out of 5 average rating, 130 reviews

Tavi Haus: Lakefront~Kayaks~SUP~Sauna~Pool Table

-Private lakefront living in a modern chalet -6-person sauna for post-adventure relaxation -Paddleboards and kayaks for summer fun -Cozy fireplace and pool table in lounge -15 mins to Sleeping Bear, 20 mins to TC -In the heart of Michigan’s wine country Hosted by Catered Stays Rentals, we cater to the ideal guest experience. Kayaks and paddleboards are seasonal amenities (May-Sept). We look forward to hosting you, where you can relax, recharge, and create lasting memories!

Top Guest favourite

Dome in Glen Arbor

5 out of 5 average rating, 227 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.

Guest favourite

Guesthouse in Glen Arbor

5 out of 5 average rating, 23 reviews

Quiet home w/ Lake Michigan view & steps from town

Relax and unwind in this calm, stylish private guest cottage with views of Lake Michigan. This cozy sanctuary is perfect for couples or individual travelers looking to enjoy the best of Sleeping Bear Dunes -- it's a short walk to downtown Glen Arbor & the Heritage Bike Trail, and a quick drive to the best trails and beaches in the area. We welcome guests of all races, faiths, genders, and sexual orientations. COTTAGE DOES NOT HAVE DIRECT BEACH ACCESS.

Top Guest favourite

Chalet in Benzonia

4.99 out of 5 average rating, 225 reviews

Creekside’s Cozy A-Frame Chalet with Pond & Trails

Enjoy the cozy vibes of this A-Frame Chalet nestled on 80 peaceful acres in Benzonia, Mi. Tucked into the heart of Northern Michigan’s beauty enjoy being surrounded by nature at the Chalet and truly unplug as this property does NOT have WiFi. A chance to getaway while remaining a close drive to Frankfort, Crystal Mountain, Sleeping Bear, and Traverse City. A perfect place to retreat or a home base for the adventurous spirit!

Guest favourite

Home in Thompsonville

4.94 out of 5 average rating, 143 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, 131 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

4.95 out of 5 average rating, 105 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.

Top Guest favourite

Farm stay in Cedar

4.97 out of 5 average rating, 346 reviews

J2 Farm Guest House

Find us on Insta @cedarnorthtc. Peaceful romantic get away in beautiful Leelanau countryside. Gentleman/lady farm with dairy goats and cow. Private, airy guest house with separate entrance, but within our home. Galley kitchen and loft for extra sleeping room are cozy additions. There are five additional places to stay through Airbnb on our property at Cedar North, check them out as well.