Family-friendly rentals near The Highlands at Harbor Springs

Harbor Springs Vacation Rental-outdoor Hot Tub

Beautiful Cedar ski chalet with large deck, located in woodsy area. Back deck with 7 person jacuzzi, get ready to relax after some skiing. Fire Pit located just off the back deck, completely covered fire pit also under deck,large gas grill on the front elevated deck. Chalet has a full kitchen. Billiards, pingpong, foosball and 6' air hockey table in the basement. Walking distance to Nubs Nob. Well trained pets are welcome for $35 nt or $150 wk. potty trained, non chewing, no going on furniture.

Highland View Cottage of Harbor Springs

Our home is beautifully decorated, spacious, and very clean. It is your home away from home. Relax and enjoy the many amenities it has to offer. Whether you like to cook or eat out, our home has all the comforts of home. It is a SMOKE FREE and PET FREE home. Our guest MAXIMUM IS 8. Highland View is a great place to gather with friends and loved ones to create memories for years to come. Other things to do: Mackinac Island 35 minutes away Fishing Golf Skiing Biking Hiking Beaches Etc.

The Nature Retreat - NEW hot tub & piano

A unique experience for people who appreciate the simple things of life - like nature, a good book and music. Located in a peaceful neighborhood near the Tunnel of Trees, Pond Hill Farm, downtown Harbor Springs, 8 minutes to Boyne Highlands and other top northern Michigan attractions. LUXARY HOT TUB INSTALLED JULY 2025. Upright piano and ukulele. House = approx. 2,800 sq. ft. You must let us know if you would like to bring 1 dog or an 8th person. Guests must be comfortable with stairs.

Lake Street Retreat - In town Harbor Springs

This Lake Street apartment is a one of a kind. The apartment is partially above commercial businesses, including your host, The Harbor Barber (no chemical services offered - so no funky odors from below). This space was 100% improved in 2021. The property is a short walk/bike-ride from the bike path, and iconic downtown Harbor Springs, the Lyric theatre, a dog beach, a bathing beach and so much more. Your host freely shares his knowledge of the history and current events happening around town.

Cozy retreat near local resorts, skiing/golf

Located just two minutes away from The Highlands and Nubs Nob ski/golf resorts, and only ten minutes away from the beautiful downtown shopping districts of both Harbor Springs and Petoskey, this charming Northern Michigan getaway is fully stocked for your vacation! This home away from home is fully outfitted to make your stay as comfortable as possible. We have also taken great care to ensure that it is one of the cleanest and tidiest homes available to you. Thank you for your consideration!

Coveside Retreat: Beach, Pools, Hiking, Skiing

This large, end-unit 5-bedroom, 3 bath condo is great for large families or gatherings of friends at Harbor Cove. Tucked into the woods with nature trails to hike, sandy lake Michigan shoreline and indoor/outdoor pools. Close to golf courses and wineries. 5 miles from Boyne Highlands and Nubs Nob, for winter enthusiasts who enjoy skiing and snowboarding. A short drive, or bike ride to downtown Harbor Springs and Petoskey for dining, movies and shopping. Note this is not a party house!

Woody’s Place on the Bike Path

Newly renovated and centrally located between Petoskey and Harbor Springs. Situated on the famed M-119, and the Little Traverse Wheelway, a bike path connecting Harbor Springs to Charlevoix. Featuring 3 private (queen) bedrooms and a 4th open sleeping loft with two twin XL built-ins. Classic northern Michigan aesthetic with all the amenities you could want while you’re away. Walk to nearby Petoskey Brewery or grab supplies for Petoskey State Park beach at Toski Sands. Your trip starts here!

Relaxing Getaway in Harbor Springs!

Located in Harbor Springs, the perfect year-round getaway in Northern Michigan awaits. Tucked away in a peaceful location, Trout Creek condos are on 150 acres with many amenities for all to enjoy! Indoor & outdoor pools, tennis courts, gym, hiking trails and more! Enjoy area golf courses, ski hills, lakefront & restaurants. -Located next to Nubs Nob and The Highlands -Complimentary shuttle to Nubs Nob (weekends) -Close to Harbor Springs & Petoskey - Mackinac Island Bridge (30 miles)

Up North Lodge that checks all boxes! W/ AC

Experience everything Northern Michigan has to offer! Our 4 BR, 2 full bath Lodge is the perfect getaway that meets all of your needs. Relax by the fire, gather in the fully equipped kitchen & entertain in the large finished basement w/ a 75" Smart TV & pool table. This four seasons offering is centrally located to Nubs Nob/The Highlands (3 minutes), Harbor Springs (8 minutes), Petoskey (10 minutes) and renowned golf courses/restaurants. Come make memories that will last a lifetime!

Harbor Springs Farm Apartment

A recently remodeled lower level apartment on a farm in Harbor Springs. Located just miles from downtown, Lake Michigan, world class skiing and golf, biking and hiking trails, this is the perfect home base for any adventure. Enjoy breathtaking views of the sunrises and sunsets on the farm out the panoramic windows. We do live upstairs and you will be able to hear us through the floors. The entire apartment is private, with your own driveway, entrance, kitchen, bathroom, and living space.

The Rhubarbary Ruins - with an outdoor sauna

We have just added an outdoor sauna to this fabulous cabin in the woods behind our house. Although there is only 1 proper bedroom there is a sleeping loft with a queen size bed and window overlooking the hardwood forest. We also have a pull-out couch. Guests have complete privacy and everything provided for a comfortable stay This is a cabin with peaceful relaxation in mind....no loud parties or anything of that nature. Come and enjoy northern Michigan's beauty in all seasons.

Disconnect at our Ski Chalet in Nubs Nob

Newly remodeled A Frame Cabin in the woods of Hidden Hamlet in Harbor Springs, Michigan. Located in the little neighborhood at the base of Nubs Nob Ski Resort, this is a peaceful and quiet neighborhood surrounded by beautiful trees. Currently we are renting this as an open bedroom loft with a queen bed. There is also a pull out sofa sleeper on the main floor, but you know the comfort level of those... Check us out on Instagram @potters_cottage