Family-friendly vacation rentals in Three Oaks

4.97 out of 5 average rating, 172 reviews

A yurt is set amidst a green landscape, with a wooden deck leading up to its entrance. A small private outhouse is positioned nearby, adorned with flowers. Overhead, a dramatic sky features varied cloud formations, enhancing the peaceful rural setting.

Yurt in Buchanan

Off Grid Yurt Glamping on Permaculture Homestead

Stay in our stylish yurt for a one of a kind "glamping" experience on a 20acre homestead! The perfect location on the Southwest Michigan wine trail and just 15 minutes to Lake Michigan beaches! Awesome ammenities - off grid solar power, private outhouse, outdoor shower, fans, fridge, grill, firepit, and more. Take the tour, meet sheep, horeses, chickens, rabbits and learn permaculture. Order our delicious DIY pancake breakfast featuring homemade maple syrup, our organic eggs and pancake batter.

A comfortable living space features a vintage green cabinet and a wooden dining table surrounded by black chairs. Natural light floods the room through large windows, enhancing the cozy atmosphere created by soft furnishings and decorative plants.

4.98 out of 5 average rating, 202 reviews

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. :)

4.93 out of 5 average rating, 165 reviews

An inviting kitchen and dining area is highlighted by a long wooden table surrounded by a mix of chairs. Natural light fills the space through large windows, illuminating the white walls and beamed ceiling. A cozy living area is visible in the background, featuring a fireplace.

Cottage in Three Oaks

The Happy Cozy-Pets Welcome, Fire Pit, Privacy

If relaxing in nature in a calm and cozy home is what you're seeking, you'll find it here! It's been designed to make you feel at peace and comfortable inside while providing several outdoor spaces for you to enjoy the sights, sounds, and smells of nature. The open floor plan and large dining table create a grand gathering space for everybody to be together and create the memories that matter most. Feel free to safely start a campfire outside or in the fireplace indoors. It's all here for you!

Superhost

An open living area features a cozy white sofa and a dark wooden coffee table. A large window offers natural light, framed by blue walls adorned with nautical artwork. The adjoining dining space is visible, showcasing a wooden table and chairs, contributing to a welcoming atmosphere.

4.86 out of 5 average rating, 110 reviews

The Lucky Charm House -Walk to it all! Cute, cute

Cute as can be, super comfy, 3 blocks to downtown 3 Oaks. Walk to Acorn Theatre, Journeyman & shopping in an eclectic quintessential small town 90 mins from Chgo. Hike local trails, beach it up at Warren Dunes State Pk, bike ride country roads -Explore Harbor Country. Wonderful dining, brew pubs and wineries to explore. Open living space w/large DR. Primary BR +bth w/shower. 2nd BR w/full bed +single bunk. Large back porch +fenced yard. 2 large TV’s, Wifi/cable. Daybed front porch.

The living room features a modern design with a mounted television above a sleek fireplace. Two comfortable armchairs flank a wooden coffee table, while natural light filters through the large windows, complemented by light-colored shades. A neutral rug adds warmth to the space.

4.98 out of 5 average rating, 156 reviews

1 Block to Journeyman - Dog Friendly/Patio/Firepit

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!

Tiny home in New Carlisle

The cabin exterior features a wooden facade with a sloped roof and a welcoming front porch. A bench sits on the porch, surrounded by potted flowers. Warm light from string lights enhances the inviting entryway, set against a backdrop of open grass and distant trees.

4.99 out of 5 average rating, 176 reviews

Cozy Cabin 2.0 Mins from Michigan’s Harbor Country

Immerse yourself in nature inside this charming cabin featuring all of the necessary amenities, including a queen-sized bed, kitchen basics, fire pit, grill, and deck. Surrounded by 40 acres of woodlands, this cabin offers a quiet retreat while being only twenty minutes from Michigan's Harbor Country. Relax inside with a book or head out to enjoy golden sand dunes, art and antiques, locally-sourced food, hiking trails, and over twenty wineries along the windy, tree-lined Red Arrow Highway.

A spacious backyard is presented, featuring a small playset with a slide and climbing area. Lush green grass provides ample room for play. The scene is framed by a wooden fence and accompanied by a hot tub visible on the patio to the right.

4.97 out of 5 average rating, 112 reviews

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!

The image displays a stylish living room featuring light-colored walls and a geometric area rug. A modern light fixture hangs above a rectangular coffee table, complemented by two leather chairs. The exterior view showcases a two-story home with a welcoming front porch and a blended color scheme.

4.99 out of 5 average rating, 115 reviews

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

A newly renovated kitchen features modern cabinetry in muted tones, with light-colored countertops and a gas range. Stainless steel appliances include a refrigerator and a coffee maker. Natural light enters through a window above the kitchen sink, creating a bright and functional space.

4.96 out of 5 average rating, 143 reviews

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!

4.98 out of 5 average rating, 123 reviews

The living room features a cozy leather sofa and two comfortable chairs, arranged around a circular wooden coffee table. Natural light fills the space through large windows, complemented by neutral tones and decorative wall hangings.

Apartment in Three Oaks

2 BD Apt Downtown, 1 Block to Journeyman & Acorn

The Sycamore Street Apartment is a thoughtfully designed space in the heart of Three Oaks, MI. This apartment is on a quiet, tree lined street just one block from Journeyman Distillery, the Acorn Theater, and the quaint shops & restaurants lining downtown Three Oaks. Enjoy small town charm while being minutes from the beaches along Lake Michigan, Warren Dunes State Park, wineries, antiquing and all that Harbor Country has to offer. We look forward to welcoming you!

Guesthouse in New Buffalo

A cozy bedroom features a spacious bed adorned with layered textiles and decorative pillows. Large windows provide views of the outdoors, while natural light is enhanced by wooden ceiling beams. A small dining area with chairs and a table is positioned nearby.

4.97 out of 5 average rating, 609 reviews

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

A charming yellow cottage is surrounded by greenery and vibrant flowers. The home features blue shutters and a welcoming front porch with white railings. A paved pathway leads to the entrance, framed by well-maintained grass and landscaping.