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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.

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!

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!

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. :)

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.

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.

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

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!

Barn of Three Oaks near Lake Michigan/Journeyman

The Barn is a three bedroom, two and a half bath home. The primary bedroom has an en suite full bath, while the front bedroom has a half bath en suite. Bedrooms are equipped with USB charging ports for three devices as well as a white noise machine. The kitchen is thoughtfully appointed as well, including a Keurig. There are many books, games & puzzles in addition to a selection of records to enjoy. A washer and dryer are also on site as well as an iron and ironing board.

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!

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!