Family-friendly holiday rentals in Three Oaks

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, private resort-style neighborhood pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax & unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!

The Craftsman- Built for families! Ideal location!

THE CRAFTSMAN is designed to be your group's perfect home base in SW Michigan! Built with families in mind, this renovated home has everything your need for a fun and hassle free stay. A large fenced backyard with fire pit & BBQ. A big rec room with foosball, video games, & toys/games for all ages. A fully equipped kitchen and plenty of indoor & outdoor space for everyone. Sleeps up to 10 people! Walking distance to all of Three Oaks and <10 minute drive to New Buffalo, wineries, beach, & more!

Orange Street Getaway - Heart of Three Oaks

Charming Two-Bedroom Home in the Heart of Three Oaks This cozy two-bedroom, one-bathroom house sits in the heart of Three Oaks with a large yard and off-street parking. Enjoy a short walk downtown to unique shops, restaurants, galleries, and the historic Vickers Theatre. Three Oaks is a quaint artsy village famous for Journeyman Distillery — known for its excellent bourbon and organic spirits — and Drier’s Meat Market. Lake Michigan beaches are just minutes away. Perfect for a relaxing getaway.

Casa Gitana - Boutique Style Stay in Three Oaks

Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

Walk to downtown Three Oaks Modern Victorian Home

Steps (0.2 mi) to Journeyman Distillery and all that downtown Three Oaks has to offer. Central to all in Harbor Country like beaches, wineries, breweries and farm stands. Come relax in style with us! Beautiful, large & comfortable vintage Victorian home with modern touches. Home features grand rooms, comfortable premium furnishings & vintage details throughout. Outside, you'll find a spacious fully fenced-in backyard, with plenty of room to play or relax in the sunshine, or by the firepit!

The Loft at the Acorn Theater

This one-of-a-kind, spacious, industrial-chic apartment is in the heart of Three Oaks historic Featherbone district. The Loft has a fully equipped kitchen, large dining table, comfy living room with a baby grand piano, and outdoor deck. Three Oaks' arts community features the acclaimed Acorn Theater, boutiques, galleries and dining options. Lake Michigan beaches, magnificent wineries, Chikaming Preserve trails, Warren Woods, and the Indiana Dunes National Park are just a short ride away.

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.

Great Yard, HOT TUB, Steps from Downtown

Welcome to the Oak St. Guest House! This 2 story single family home is just steps from local dining, including Journeyman's Distillery. Fully appointed, the home features a renovated kitchen, spacious dining room & living space. With 4 bedrooms and 2 baths, it is the perfect place for family celebrations or a home-away-from home for your entire wedding party. Featuring a vastly sized backyard, fire-pit, and grill - the Oak St. Guest House is perfect start to your summer lake vacation!

2 blocks to Journeyman, 12 mins to Beach, King Bed

Highlights: ✔ Designer rehab in 2022 ✔ Sleeps 8 ✔ Outdoor firepit ✔ Relaxing back porch ✔ 5 min walk to Journeyman ✔ Easy 5-10 min walk to Three Oaks dining + shopping ✔ 8 min to wine tastings ✔ 10 min to New Buffalo, Union Pier, Sawyer ✔ 12 min to beach ✔ Gas BBQ grill ✔ Smart TVs & board games ✔ King bed in main bedroom ✔ Fabulous front foyer for wedding photos ✔ EV charger ✔ Luxury custom-designed home ✔ 3 vehicle parking ✔ Computer workstation ✔ High speed wifi ✔ Fully stocked

The Heartwood House<3 : DT Three Oaks w/Game Room

Newly renovated 1920's Bungalow loaded with character. Spacious interior with a mix of modern and vintage furnishings that will leave you relaxed and rested. Large private backyard with grill and firepit to enjoy starry Three Oaks nights. Only 4 blocks from Journeyman Distillery and close to all of the restaurants and shops in downtown. Perfect place to stay for a wedding or getaway near wineries, breweries and beaches. Come see the village that everyone is talking about!

The Sycamore Guesthouse, Across from Journeyman.

Located just steps to Journeyman Distillery! Contemporary furnishings meet within a restored Victorian home with modern conveniences. Spacious wrap-around covered porch for outdoor relaxation. Each of the five full bathrooms feature a multi-zone shower and beautiful tile work. There are a total of 5 queen beds, 2 full beds and a portable crib making room for 14 adults + children. (You can bring in additional portable cribs.) Minimum age for group rentals is 25 years of age.

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!