Three Oaks Vacation Rentals

Enjoy a creative countryside escape with Juniper’s Three Oaks vacation rentals. Located in the heart of Harbor Country, Three Oaks is known for its historic downtown, independent shops, local food and drink, arts venues, and easy access to farms, wineries, and Lake Michigan beaches.

Juniper’s Three Oaks properties offer a comfortable home base for guests who want small-town character with plenty to explore nearby. Whether you’re planning a weekend around dining and shopping, a wedding stay, a wine country visit, or a quiet retreat close to the lakeshore, Three Oaks delivers a distinctive Southwest Michigan experience.

Why Our Three Oaks, MI Properties Are the Best

Three Oaks stands out for its artsy, independent spirit. Guests can catch a film or event at the historic Vickers Theatre, browse local boutiques and galleries, visit Journeyman Distillery, or explore nearby farms, markets, and scenic country roads.

Unlike the busier beach towns, Three Oaks offers a more inland, village-centered stay while still keeping Lake Michigan within easy reach. New Buffalo, Union Pier, Lakeside, Warren Dunes, and several Harbor Country beaches are just a short drive away, giving guests the flexibility to enjoy both countryside charm and shoreline adventure.

For travelers searching for Southwest Lake Michigan vacation rentals with a quieter, more local feel, Three Oaks is a standout choice. With Juniper, guests can enjoy well-maintained homes, inviting amenities, and convenient access to the food, art, farms, and natural beauty that make this town so memorable.

Properties Available 8 properties available
Upon walking in the front door, the charming coziness of the spacious living room invites you into a relaxing vacation atmosphere. With lots of comfortable seating options—including some vintage antique chairs—a gas fireplace, and a flat-screen TV, it’s a popular gathering spot. But then, so is the large, deluxe kitchen island, where drinks, snacks
The Fourth Oak
The Fourth Oak
House Pet Friendly Location Three Oaks, MI
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 8 guests
Rating 4.8 (37)
Stepping inside Gray Haven, you and your guests will find yourselves immediately relaxing and breathing easy, given the spacious, rich atmosphere created by the vaulted ceilings and magnificent views of the surrounding woods, the pool, and large deck through the home’s expansive windows. Add to that the breathtaking natural light and stylish, hand-
Gray Haven
Gray Haven
House Pet Friendly Location Three Oaks, MI
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 8 guests
Rating 4.9 (20)
The Loft’s main living area opens with natural light and warm, inviting finishes. Soft textures and refined seating frame the room, while adjoining kitchen is defined by its mint-green refrigerator, wide farmhouse sink, and broad island for everyday meals. The space feels calm and refined beneath its timber beams.The sleeping area features a Queen
Berrywood Loft
Berrywood Loft
Loft Location Three Oaks, MI
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Inside, the house has a fresh, polished look. Sliding glass doors open the main living area to the deck with outdoor dining seating, and the fireplace gives the living room a serene ambiance after dark. The kitchen sits at the center of the house with white cabinetry, stainless appliances, open shelving, and a large island with seating. Just beyond
Cozy Haven
Cozy Haven
House Pet Friendly Location Three Oaks, MI
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4 (1)
Designed and built by UrbanLab Architects, Owlwood is a unique multi-wing home where every element has been executed to perfection. Set against a panoramic backdrop of peaceful forest views in the middle of Harbor Country, the showstopper at this stunning house is the modern architectural design that allows pure natural light to be enjoyed from nea
Owlwood
Owlwood
House Pet Friendly Location Three Oaks, MI
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 9 guests
Rating 5 (28)
Encompassing 33 beautiful acres in Harbor Country, this historic estate offers room for large groups, with open lawns, wooded paths, and ponds suited to fishing and canoeing. The landscape gives you plenty of ways to spend time outside, including long walks, quiet corners, and a seasonal pool for warm-weather days. Homesteaded in 1836, the estate i
Berrywood Farm
Berrywood Farm
Farm stay Location Three Oaks, MI
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
Rating 5 (13)
The Cottage’s main level opens with generous light and warm natural materials. A wood-burning fireplace is the focal point of the room, framed by tall windows and soft textures. Seating includes a queen pull-out sofa for additional guests, arranged for reading, quiet time, or evenings by the fire. The dining area connects to a bright galley kitchen
Berrywood Cottage
Berrywood Cottage
House Location Three Oaks, MI
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (2)
The Farmhouse includes 3 refined living areas suited to time together. The main great room centers on a brick fireplace and generous seating for movies or conversation. A bright sunroom offers a contemporary lounge with wide farm views, while the front sitting room provides a quiet place to read or settle in at the end of the day. The kitchen pairs
Berrywood Farmhouse
Berrywood Farmhouse
House Location Three Oaks, MI
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (2)

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