Holiday rentals in Cleveland

Creekside Hideaway

Adorable two bedroom above-garage apartment in beautiful Leelanau County, right in the heart of Sleeping Bear Dunes. Set back on 10 wooded acres and right on Shetland Creek, this location is perfect for an up north getaway! Close to wineries, golf courses with Lake Michigan, Lime Lake and Little Traverse Lake all right nearby. Just a short drive to Glen Arbor and Leland. The Heritage Trail is also down the road. Spend the day exploring then relax by the creek in the evening with a glass of wine!

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

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.!

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!

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!

Vineyard Cottage | Barrel Sauna on a Vineyard!

The Vineyard Cottage is a charming 4-bedroom home located in the heart of Leelanau's wine country by Aurora Cellars. This property overlooks estate vineyards, the boutique winery, and beautiful rolling countryside. Enjoy our barrel sauna with panorama views! Aurora Cellars is open year round, so stroll over and have a glass of wine or flight during your stay and enjoy the beautifully manicured property and vineyard trails or explore Leelanau County from this centrally located oasis.

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!

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 Townhouse Retreat at Sugarloaf

Excellent site for couples or families, enjoy access to hiking, swimming, golf, scenic views and access to shopping and other amenities in nearby Leland or Glen Arbor. Several wineries are also nearby. The pool is open from Memorial Day through Labor Day weekend. Two golf courses are immediately adjacent to the association property--Sugarloaf the Old Course and Manitou Passage.

Birch Le Collaboration House

Birch Le Collaboration House was designed as the ultimate Hygge Supply Home. Established to showcase our sustainable partners and modern design, the home offers a unique experience integrating architecture and nature. Centrally located near quaint towns, beaches, wineries and hiking, the home is a great gathering spot in any season to entertain family and friends.