House holiday rentals in Shorewood-Tower Hills-Harbert

Couples alert! PVT beach access, hot tub, firepit!

ADORABLE LAKESIDE COTTAGE W/YEAR-ROUND HOT TUB AND A GUEST FAVORITE - ACCESS TO SEMI-PRIVATE LAKE MICHIGAN BEACH SHARED BY JUST 10 HOMES SO IT'S NEVER CROWDED! BEACH ACCESS GATE IS 7 MIN WALK FROM COTTAGE. LOFT LIKE HOME IS SUPER CLEAN WITH VERY COMFY KING SIZE BED AND ONE PULL-OUT COUCH FOR 4 GUEST (MAX). FIREPIT SUPPLIED WITH WOOD, AN OUTDOOR PATIO AND WEBER GRILL - YOU WILL LOVE IT! Bike/walking path out front and just 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!! HURRY!

Happy Acres: Modern Luxury Country Farmhouse

Happy Acres is a modern oasis that’s close to beaches, wineries, restaurants & shopping and far enough removed to watch the stars glisten from your outdoor living space. Perfect place to get away & relax. Short drive to New Buffalo restaurants and shopping, Union Pier and Warren Dunes. Enjoy beaches, hike sand dunes, visit local wineries and breweries and antique. Three Oaks is a few minutes away-- enjoy restaurants, art galleries, Journeyman Distillery and Acorn Theater. South Bend is 35’ drive

-The District 5 Schoolhouse-

The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

Charming Downtown Sawyer Home Close to the Dunes

Enjoy this charming home in the heart of downtown Sawyer. Venture out on foot, and you're a 2 min walk to Greenbush, Infusco, Section House and more. Hop in the car and be at Warren Dunes or Journeyman Distillery in under 10 mins. Centrally located to be close to everything Harbor Country has to offer. Inside you'll find all the comforts of home, including a full kitchen, plush queen beds, as well as a 55" Smart TV with many apps ready to go on the Apple TV. Kitchen & bathroom basics provided.

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

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.

Designer's Own Cozy Cottage

Kick back and unwind in this stylish getaway, ideally located in Union Pier and just a five-minute drive to New Buffalo. Tucked on the lake side of Red Arrow Highway, the Casita offers the perfect balance - close to all the action, yet a quiet retreat to call your own. Guests love visiting nearby beaches, indulging in baked goods, ice cream, local restaurants and wineries. Bike trails, hiking, pickle ball, golf and kayaking all nearby. Endless opportunities for relaxation and adventure await!

1 Block to Journeyman | Pets | Dunes & Beaches

Our newly built (2022) home is located just 1 block to Journeyman Distillery and the quaint downtown of 3 Oaks. Our home has been thoughtfully designed to create a serene and memorable stay for our guests. Eclectic shops, restaurants, and galleries are a short walk away. Drive to local beaches in less than 15 minutes. Spend your day exploring Harbor Country - wineries, breweries, hiking, biking, golf, beaches, blueberry picking, antiquing, and so much more. 3 Oaks is at the center of it all!

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.

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.

Dog Friendly Downtown Three Oaks Cottage! Fenced!

Just a short walk to charming downtown Three Oaks, home of the famous Journeyman’s Distillery and all the shops and eateries Three Oaks has to offer. It is also a quick drive to the beautiful beaches at Warren Dunes State Park and New Buffalo. This cheerful home has queen beds and a fully stocked kitchen. Plus a huge fenced-in back yard, so bring the kids or the dogs and know they are safe while you relax in the three-season room or on the outdoor deck!

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

Summertime at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. This designer-owned haven offers both deep seclusion + an open-format layout that invites connection to loved ones and nature + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.