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!

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!

Dome in Suttons Bay with amazing views!

Amazing Views -- Unique Architecture -- Great Location One of the best views on Leelanau Peninsula. Mini-Dome (guest house) sharing 5+ acre property with Big Dome (main house). Conveniently located near the M-22 scenic route, 1 mile from the bike Trail, and within 4 miles of 6 wineries. The interior was newly renovated in 2019. The Mezzanine has 2 queen beds (shared space). You'll love this unique and romantic escape. 2022 Stats: 3 engagements, 6 Anniversaries, 5 birthdays, 4 pre-weddings

Hillside Haven - On 10 acres located near Lake MI.

Cozy home on 10 acres located near Lake Michigan beach access. Perfect for couples or families looking to get away. Close to Traverse City, Frankfort, Sleeping Bear Dunes and so much more. Pet friendly, professionally cleaned. Keurig coffee provided. Fast wifi, streaming TV, central A/C, washer and dryer, refrigerator, oven, microwave, dishes, and towels all included. Pack and play and toddler cot provided. Hunters welcome during hunting season. Boat launch and snow mobile trails also nearby.

Lime Lake Therapy-HotTub/PingPong/Private Dock/AC

Quintessential up north cabin beautifully situated on a private hilltop setting with stunning lake views. Immaculate with soaring ceilings, open floor plan, & solid surface counters. Main floor master bedroom suite overlooking the sparkling blue waters of Lime Lake. Front porch and covered lakeside deck for enjoying nature and gorgeous water views. Private frontage across the street with a NEW dock, fire pit and picnic area. Pure, beautiful Leelanau at its best! 39 min. to ski Crystal Mt.!

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.

CaterCasa: Fenced Yard~Dog Friendly~Games~Sauna

🐶 Dog & Kid-Friendly Yard 🎲 Indoor Shuffleboard 🧖 Relaxing Sauna 🌲 Near Long Lake & Timbers Rec 📍 7 Miles to Downtown TC 💻 Fast Wi-Fi & Workspaces Hosted by Catered Stays Rentals, we’re committed to creating the perfect guest experience. This home features a fenced backyard, shuffleboard, sauna, and inviting spaces inside and out—just 7 miles from downtown Traverse City. With plenty of room for family, friends, and pets, it’s designed for comfort, convenience, and memorable stays.

Comfy Townhouse in Lovely Leelanau~

Great location in central Leelanau county, about 20-30 minute drive from major sites of interest: Sleeping Bear Dunes, Traverse City (Cherry Festival and Film Festival), Leland Fishtown, Sutton's Bay, Interlochen, wineries/cideries/breweries/distilleries, beaches, etc. Renovated and redecorated first floor makes the condo a wonderful place to relax and kick back. Come and explore all the area has to offer: summer vacations, fall color and wine tours, winter sports, spring blossoms!

Lemon Drop Cottage

This place is a winter and summer wonderland. Our cottage is a small 50's style with much character tucked away in the woods. We’re surrounded by the 70,000 acre Sleeping Bear Dunes. There’s plenty of skiing, canoeing, hiking and fishing, peace and quiet. We're on the boarder of Benzie and Leelanau Counties, the best of wine regions this side of the Mississippi and a true artisanal food destination It's a short drive to Honor, Empire or Glen Arbor. Traverse City is 25 miles east.

Exodus: Luxury Tower- Hot tub 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

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!

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.