Family-friendly holiday rentals in Shorewood-Tower Hills-Harbert

The Cottage of Harbor Country - Close to it all!

Welcome to your very own Cottage in Harbor Country! The perfect weekend getaway from Chicago, our cottage is close to Warren Dunes and just a 15-20 minute walk to Lake Michigan. Renovated and beautifully appointed, it blends vintage charm with modern updates! Enjoy morning coffee on the new deck or screened-in porch, take a dip in the new hot tub, or cozy up next to the wood-burning fireplace. Enjoy the perfect place to relax, hike, go antiquing, wine-tasting, and make memories with loved ones!

Indoor spaces · Family · Parking

The Walnut House, Michigan Woods Retreat

Beautifully designed home, surrounded by trees. 5 minutes drive from the white sandy beaches of Lake Michigan, and conveniently close to historic Three Oaks downtown: Journeyman whiskey distillery, Acorn Theater, Froehlich's bakery and deli, Patellie's pizza and more. The home has beautiful large windows in every room and bedroom. It is well stocked with books, thoughtfully appointed rooms that are perfect for a quiet escape, family retreat, and home base for exploring the areas activities.

Family · Indoor spaces · Hiking

Lakeside Retreat Nestled Among the Trees

Please note: Summer stays are 7 night minimums from Friday to Friday. Welcome to our cozy 'Tree House,' nestled among the trees in Lakeside, Michigan! Our renovated cottage is 90 minutes from Chicago in the heart of Harbor Country. Our bright, open home features high end finishes and luxury mattresses. Nature-inspired hues invite you in, making relaxation a top priority! Generous outdoor spaces include a deck with dining area, rocking chairs, and two fire pits for s'mores under the stars.

Kitchen · Indoor spaces · Amenities

The treehouse at Warren Dunes

Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

Indoor spaces · Family · Outdoor spaces

Lola's Pine Tree Cottage

Lola's is a uniquely perfect old-school Michigan Beach cottage, with a brand new, updated kitchenette & shower! Enjoy the quiet of 1.5 acre of yard & forest (with friendly deer and wild turkeys!); walk to the beach; snuggle in front of the fire and under historic pines! Perfect hideaway all year round! Close to all the charms and amenities of Sawyer, Three Oaks, Union Pier, New Buffalo, and St. Joes. Excellent writing retreat, we’ve been told, and a sweet spot for a romantic getaway!

Indoor spaces · Family · Amenities

Hot tub open year round in modern/rustic cottage!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 3 bikes! So close to boutiques, coffee shops and cute restaurants!

Kitchen · Family · Laundry

Family Getaway with Year Round Hot Tub!

Welcome to Harbert in Harbor Country! The House on the Prairie is tucked away in a quiet location in Harbert, yet minutes from the beaches, dunes, breweries, wineries and all the Harbor Country attractions. The house features tons of amenities and is packed full of games, toys, books and activities for all ages. Enjoy the back yard amenities with a hot tub, firepit, hammock & deck! Even includes a tree house, sandpit and trampoline for the kids! Hot Tub open all year round!

Family · Kitchen · View

Darling Home + Hot Tub by Warren Dunes + Wine Bar

Cozy up to this darling get-away right next to the cutest wine bar in the midwest (Out There) and just a short walk to Warren Dunes State Park and the beach. This family-friendly home is ready for you to explore all the treasures of Southwest MI: biking, hiking, beaching, and more. Then come back "home" to this newly remodeled house for playing games, firepit, and dipping in the hot tub. 3 bedrooms + small office, 2 full baths, a great room, eat-in kitchen, and big backyard.

Kitchen · Family · Layout

The Dacha • Hot Tub, Family-and-Dog-Friendly House

A four-minute walk to town and a quick drive to everything Harbor Country has to offer! "Dacha" is the Ukrainian word for a country house where the whole family gathers. Relax in a hot tub facing the woods, watch your kids play from the deck, enjoy coffee and sunrise on the front porch, have a glass of wine on the screened-in back porch, roast s’mores at the fire pit, read quietly in one of our reading nooks - these are only some of your options when you stay at The Dacha.

Kitchen · Family · Grill

Morton's Retreat Cozy 1 Bedroom Apartment

Cozy comfort close to Michigan's most popular state park, breweries, wineries, antique malls and farm-to-table restaurants. Morton's Retreat has plenty of room to relax. Charcoal grill and fire pit (shared with Morton’s other retreat) for use in a spacious yard. Private entrance with keyless entry makes check-in a breeze. One other Airbnb located next door in same building. Two complimentary seltzer waters and snacks are provided to help kick off your stay.

Family · Indoor spaces · Comfort

Cozy Chalet by Lake MI&Dunes with Fire Pit

Sawyer Gem: Cozy Vintage Retreat Near Lake & Dunes! Charming vintage chalet sleeps 4 . Sun-drenched sunroom, private fire pit. Walk to restaurants, bars, antiques. Minutes to Lake Michigan & Warren Dunes. Adding to its unique charm, The Cozy Chalet is directly connected to Harbor Country Mission, a wonderful antique shop supporting the local community. You'll enjoy a separate entrance for complete privacy and convenience.  Book your stay today!

Kitchen · Indoor spaces · Bathroom

Sunflower Cottage: Relax near Warren Dunes

Stylishly renovated, this quiet cottage is located 1.5 miles from the entry to Warren Dunes State Park and minutes to restaurants and shops. Sunflower Cottage offers a place to unwind while having modern amenities like a fully equipped kitchen, high-speed WiFi, Smart TV, keyless entry, free laundry, outdoor shower and modern furnishings. Sunflower Cottage occupancy is limited to 4 including infants.

Family · Indoor spaces · Amenities