Holiday rentals in Cleveland

Hawks Nest Hideaway | 2BR | Screened In Deck

Welcome to your home away from home while exploring the natural beauty of northern Michigan. This newly renovated 2-bed/2-bath condo has been thoughtfully designed with comfort and style in mind. Hangout in the family room with ample seating and a smart TV with cable and streaming apps. Relax on the screened-in patio among the pines, with peek-a-boo views of Lake Michigan. Enjoy home cooked meals in a fully stocked kitchen. Location is perfect for easy access to everything the area has to offer!

Secluded Dome House w/view of Glen Lake. Sauna

Enjoy the sounds of nature and a view of Glen Lake when you stay in this unique Dome House. It is secluded but close to Glen Arbor, Crystal River, Palmer woods MTB trails, Glen Lake, and hikes on Sleeping Bear Sand Dunes. The house is perched up on a hill with a wrap around deck to enjoy the views and an outdoor fire pit also with a view of Glen Lake. Or enjoy the view from inside with the wood stove. Within a 5 min drive you can get to a public access for Glen lake or Lake Michigan.

HottubAfterDune Delight |5BR|River|Kayaks|Beaches

🏞️ Perfect Location – 3-minute drive to Downtown Glen Arbor, 11 minutes to Sleeping Bear Dunes, and 8 minutes to Glen Lake Beach Park! 🚤 Riverfront Fun – Enjoy kayaking on Crystal River and float to downtown Glen Arbor or Lake Michigan beach. 🍳 Two Fully Equipped Kitchens – Yes, there are 2! 🐾 Pet-Friendly – Bring up to 2 dogs ($250 pet fee) and enjoy the riverfront views. 🏡 Spacious & Cozy – 5 bedrooms, 2.5 baths, and room for up to 13 guests, perfect for family getaways and groups!

Great Location-Kid Friendly-M22-SleepingBear-Beach

Discover the perfect large family, multi family, couples, girls/guys retreat at the Sleeping Bear Den. 🌲 Private house tucked back in 7.2 acres of woods 👶 Designed for Families 🏖️ Close to beaches ☀️ Sleeping Bear Sand Dunes 🚘 M22 🍁 Experience Fall Colors 🍷 Perfect for Wine Tours ⛳️ Ideal Golf Getaway ❄️ Skiing and Snowmobiling Heaven 🚲 Palmer Woods Forest Reserve for hiking & biking 🌆 Traverse City *You must have an AWD vehicle in the winter for the long, uphill driveway.

Soo House

Soo is a very fun cedar shake cabin on 15 forested acres, surrounded by trails, a loon call from Glen Arbor. This scandi-eclectic, cozy spot is a dappled dirt road away from Port Oneida/Good Harbor Bay Beaches and Pyramid Point. Soo stewards a half-mile of private trails on the property itself and borders 27+ miles of maintained MTB/hike/ski trails via the Palmer Woods and Krumwiede Forest Reserves. Soo is the unique family basecamp for your Sleeping Bear Nat'l Lakeshore adventures!

Meadow Cabin at Parcel

Featured in Domino Magazine: “Midwest on the Outside, Copenhagen on the Inside.” The Meadow Cabin sits amongst a flowering and native meadow. It is our largest cabin, with room for six people. Cedar siding and expansive windows at the Meadow Cabin combine the spirit of a Scandinavian retreat with a nod to regional Northern Michigan architecture. Two main-floor bedrooms, a second-story loft bedroom, two bathrooms, and a big open living + kitchen space make up the Meadow Cabin.

Glen Arbor-walk to town-Home Theater-Pool Table

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.

Hygge Sunrise Lane

Sunrise Lane is the OG - the first home built by Hygge Supply. The home sits on a tranquil stretch of preserved wetland that leads to lakeside access to stunning Lake Leelanau. The floor-to-ceiling windows allow you to feel one with the outdoor surroundings. Views of tamarack trees, cattails, and wetland flowers, the wildlife thrives on this protected piece of property, so expect to see deer, rabbits, squirrels, birds, fireflies, and an occasional bobcat sighting.

Glen Arbor Waterfront Condo - Great Lakes 43

Come visit our peaceful retreat in Glen Arbor with stunning Lake Michigan views. Located in The Homestead Resort, enjoy our scenic riverfront location with beach access right outside your door. Our 3 bed / 2.5 bath unit accommodates 6 people with additional sofa bed if needed. We also have 2 kayaks for you to enjoy. Please review house rules before requesting a booking to make sure this property is the right choice for your group.

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.

Leelanau Day Tripper - Modern Barndominium Retreat

Welcome to your Northern Michigan Escape: Discover a modern barndominium in the heart of Leelanau County — perfectly positioned between Lake Michigan’s white sand beaches, the Sleeping Bear Dunes, and 23 local wineries. Whether you’re sipping wine under the stars, pedaling scenic trails, or relaxing with family, Leelanau Day Tripper is your stylish and serene basecamp for adventure.