Family-friendly holiday rentals in Harbor Springs

The Bird’s Nest

Welcome to the bird’s nest! A cozy open floor plan loft overlooking Main St. in the heart of downtown Harbor Springs. Built in 1881, this is one of the first structures built in Harbor Springs! Loaded with historical charm and character, and meticulously updated, this space lends itself to romantic dinners on the back deck or entertaining around the large kitchen island The property has been updated and offers modern amenities to include: new appliances, wi-fi, smart TV, and Sonos sound system.

Family · Indoor spaces · Bathroom

Cozy Aframe on Tunnel of Trees Harbor Springs

Cozy A-frame perfectly located minutes from downtown Harbor Springs. Nestled in the trees across from a nature preserve so you get that “cabin-in-the-woods” feel while being close to everything the area has to offer. Perfect homebase for “Up North” adventuring: •5 min from downtown Harbor Springs •20 min from Petoskey •40 min to Mackinaw •10 min to Nubs Nob/Highlands •5 min to Tunnel of Trees M-119 Home Features: •2 bdrms w queen beds •Indoor & Outdoor firepit •Stocked kitchen •Front/back deck

Indoor spaces · Family · Quiet

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.

Kitchen · Indoor spaces · Location

Little Moose Lodge overlooking Lake MI

Breathe in the tranquility that only comes from being surrounded by nature. With Lake Michigan in front and woods in back you get the best of both worlds during your stay at Little Moose Cabin. We are located on M119, the historic "Tunnel of Trees" highway less than 20 mins from Harbor Springs, The Highlands Resort, Nubs Nob Resort, and 45 minutes from Mackinaw Bridge. This classic 2 -bedroom 1 bath cabin has a woodstove, outdoor firepit, BBQ grill, and access to a private beach on Lake Mi.

Indoor spaces · Kitchen · Outdoor spaces

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.

Indoor spaces · Kitchen · Biking

Harbor Retreat |Private Hot Tub|Game Room|Ski+Golf

Relax and getaway with friends and family at our peaceful, charming 5BR home. Sitting upon a hill just 4 mins outside of Harbor Springs, you can enjoy the serene feelings of the countryside while being just minutes from the city. Ample space for comfortability while enjoying family memories together. Equipped with a full game room, hot tub, fire pit and more to accommodate family fun. Harbor Springs-4mins Boyne Highlands-7mins Nubs Nob-9mins Petoskey state park-12mins Tunnel of trees-11mins

Kitchen · Indoor spaces · Getting around

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!

Kitchen · Family · Condition

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!

Indoor spaces · Kitchen · Parking

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.

Kitchen · Family · Access

The House Next Door: In-Town Harbor Springs

The House Next Door is a vintage-chic modern cottage in the heart of Harbor Springs. Nicely designed throughout, perfect for staying in or to be your home base for endless local activities, many without getting in your car. 8 minute walk to waterfront, restaurants and shopping. Minutes from hiking, biking, beaches. 10 minute drive to ski/golf resorts. A block back from the bluff, close to the hustle of our busy resort town but separated enough for peace and quiet and sounds of nature.

Kitchen · Family · Skiing

Guest Suite near Cross Village

Enjoy summer days or wintry splendor. We are located in a rustic area of northwest Michigan, 15 miles north of Harbor Springs, within 2 miles of the Tunnel of Trees. We are conveniently located for nature preserves, hiking trails, beautiful beaches, ski slopes, and Mackinaw Island. Our home is attached to the guest suite but guests access their suite via a secured private entrance. Our equipped kitchen has a pantry, fresh farm eggs, butter, a home-baked item, ground coffee, and teas.

Family · Kitchen · TV

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.

Indoor spaces · Family · Layout