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Family-friendly vacation rentals in Three Oaks

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Quick stats about vacation rentals that are family-friendly in Three Oaks

  • Total vacation rentals

    Explore 60 vacation rentals in Three Oaks

  • Nightly prices starting at

    Three Oaks vacation rentals start at G$35,567 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,470 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Three Oaks vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Three Oaks rentals

  • 4.9 Average rating

    Three Oaks stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Three Oaks

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A large screened front porch is furnished with several wooden rocking chairs and a wicker seating area. Natural light filters through the screens, showcasing the surrounding greenery. A small table sits centrally, creating an inviting space for relaxation and conversation.
Cabin in Three Oaks

Cabin with POOL in family resort!

Nestled within a gated 67-acre resort and just minutes from the shores of Lake Michigan, this charming cabin offers a peaceful retreat ideal for couples, families, or solo travelers, blending rustic décor with modern comforts. Guests can spend their days exploring nearby nature trails, lounging by the pool, paddling across the lake, or unwinding on the porch. The perfect vacation for exploring nearby orchards and countryside, catching live music or theater, or just slowing down and recharging!

4.85 out of 5 average rating, 125 reviews
Guest favorite
The living room features a spacious layout with comfortable seating on a grey sofa and light-colored armchairs. A wooden coffee table is centered on a soft area rug. Natural light filters through large windows, enhancing the warm ambiance created by the historic details and wooden trim.
Home in Three Oaks

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!

4.94 out of 5 average rating, 109 reviews
Superhost
Home in Three Oaks

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.

4.83 out of 5 average rating, 131 reviews
Top guest favorite
Home in Three Oaks

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. :)

4.96 out of 5 average rating, 285 reviews
Top guest favorite
The living area showcases a modern design with a black sectional sofa and comfortable armchairs. A wooden coffee table is positioned at the center, and wooden beams complement the ceiling. A staircase leads to an upper level, while a large circular mirror enhances the space.
Home in Three Oaks

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.

4.97 out of 5 average rating, 249 reviews
Top guest favorite
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.
Home in Three Oaks

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!

4.98 out of 5 average rating, 199 reviews
Guest favorite
A bright and airy living space reveals a cozy area featuring a light-colored ottoman and a sleek fireplace. A large indoor plant adds a touch of greenery, while a doorway leads to a well-lit bedroom area beyond. Modern furnishings are visible within the serene environment.
Home in Three Oaks

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!

4.87 out of 5 average rating, 134 reviews
Superhost
A spacious dining area features a wooden table surrounded by chairs, illuminated by natural light from large windows. Artwork is displayed on the wall, and comfortable seating is available in a cozy corner. Exposed brick and wooden flooring add to the industrial-chic ambiance.
Apartment in Three Oaks

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.

4.82 out of 5 average rating, 113 reviews
Top guest favorite
Home in Three Oaks

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!

4.97 out of 5 average rating, 128 reviews
Guest favorite
Bungalow in Harbert

Family Getaway with Year Round Hot Tub!

Welcome to Harbert in Harbor Country! The House on the Prairie is tucked away in a quiet location in Harbert, yet minutes from the beaches, dunes, breweries, wineries and all the Harbor Country attractions. The house features tons of amenities and is packed full of games, toys, books and activities for all ages. Enjoy the back yard amenities with a hot tub, firepit, hammock & deck! Even includes a tree house, sandpit and trampoline for the kids! Hot Tub open all year round!

4.97 out of 5 average rating, 234 reviews
Top guest favorite
Home in Three Oaks

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.

5.0 out of 5 average rating, 119 reviews
Top guest favorite
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.
Home in Three Oaks

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!

4.98 out of 5 average rating, 173 reviews

Popular amenities for Three Oaks family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A spacious screened-in porch is adorned with comfortable seating and decorative pillows. Large windows allow natural light to fill the area, while a decorative table at the center holds a selection of refreshments. The serene view of the surrounding landscape enhances the inviting ambiance.
Cottage in Harbert

Hot tub open year round in modern/rustic cottage!

4.97 out of 5 average rating, 198 reviews
Guest favorite
A spacious living area features large French doors that open to a deck. A neutral-toned sofa is adorned with decorative pillows, while a wooden coffee table sits in front. An inviting armchair and framed artwork complement the warm, natural lighting filtering in.
Cottage in Three Oaks

The Cottage of Harbor Country - Close to it all!

4.97 out of 5 average rating, 144 reviews
Top guest favorite
A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.
Cottage in Union Pier

Designer Cottage Relax Pool Beach & Spa—Windjammer

4.97 out of 5 average rating, 250 reviews
Top guest favorite
A cabin exterior is presented, featuring a screened-in porch that offers comfortable seating. The structure, painted in a muted green tone, is surrounded by trees and foliage. A set of steps leads to the porch, creating easy access to the welcoming retreat.
Cabin in Union Pier

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace

4.98 out of 5 average rating, 180 reviews
Superhost
An inviting outdoor seating area features a stone patio with a dining table and chairs under a sleek umbrella. A fire pit is centrally located, surrounded by cozy logs. The cottage background showcases large windows and a distinctive white brick chimney, framed by lush greenery.
Home in Union Pier

Barn & Beach New Buffalo / Union Pier

4.9 out of 5 average rating, 257 reviews
Guest favorite
Home in Sawyer

Atomic Acres- Pool, Hot tub, Fire pit & more

4.96 out of 5 average rating, 103 reviews
Top guest favorite
Home in Three Oaks

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

4.99 out of 5 average rating, 112 reviews
Top guest favorite
A spacious wooden deck includes a hot tub surrounded by lush greenery, providing a serene outdoor setting. A white dining table with chairs allows for meals outside, while a large blue umbrella offers shade. The scene is complemented by a simple decorative plant centerpiece.
Cottage in Sawyer

The Dacha • Hot Tub, Family-and-Dog-Friendly House

4.99 out of 5 average rating, 132 reviews

Family- and pet-friendly home rentals

Guest favorite
The exterior of a charming barn-style home is showcased, featuring a distinctive arched roof, large double doors, and black shutters. Two potted plants frame the entrance, with a welcome sign visible above the door. A grassy area and gravel pathway lead to the entrance.
Barn in Three Oaks

Barn of Three Oaks near Lake Michigan/Journeyman

4.89 out of 5 average rating, 151 reviews
Top guest favorite
A bright living area features a comfortable gray sofa adorned with decorative pillows, paired with a light brown armchair. Large windows provide views of lush greenery, while a striped rug anchors the space. A coffee table with a bowl sits at the center, enhancing the cozy atmosphere.
Home in Sawyer

The treehouse at Warren Dunes

5.0 out of 5 average rating, 153 reviews
Superhost
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

4.92 out of 5 average rating, 209 reviews
Top guest favorite
The cabin's exterior is framed by colorful autumn foliage, with vibrant red leaves and dappled sunlight filtering through the surrounding trees. Stone steps lead to the entrance, enhancing the rustic charm of the well-maintained landscape.
Cabin in Michiana

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago

4.96 out of 5 average rating, 256 reviews
Top guest favorite
A cabin-style home is nestled among tall pine trees, featuring a large facade with distinctive tall windows that allow natural light to flood the interior. Colorful chairs are positioned on the screened porch, surrounded by well-maintained greenery and flower beds.
Cottage in Union Pier

"The Pines" in Union Pier: Year-round getaway

4.98 out of 5 average rating, 272 reviews
Top guest favorite
A cozy cottage interior features a warm-toned wooden structure with a spacious bed adorned with a patterned coverlet. A microwave is placed on a cart near a door painted in a muted tone, while books are neatly arranged on a dark shelf. Natural light enters through a window with light curtains.
Guesthouse in New Buffalo

Rainbows End 🌈 Puryear

4.97 out of 5 average rating, 535 reviews
Guest favorite
Home in Buchanan

-The District 5 Schoolhouse-

4.92 out of 5 average rating, 141 reviews
Top guest favorite
The exterior of the cottage is showcased, featuring a welcoming dark grey facade. The front yard contains well-maintained greenery and small trees. Two large picture windows allow natural light into the interior, while a small patio leads to the entrance.
Cottage in Union Pier

Camp Wanderlust-Cozy lodge-20 minute walk to beach

4.9 out of 5 average rating, 202 reviews

Family-friendly home rentals with a pool

Top guest favorite
A charming ranch-style house is situated on a spacious green lawn, surrounded by mature trees. The front features a welcoming porch with seating, and a driveway leads to an attached garage on the right. Lush landscaping enhances the tranquil setting.
Home in Bridgman

Cozy Ranch | Huge Fenced Yard| Fall Fun

4.98 out of 5 average rating, 100 reviews
Top guest favorite
A charming cottage exterior is shown with large windows allowing ample natural light. Lush landscaping surrounds the entrance, featuring ornamental grasses and rocky accents. The inviting covered porch provides a welcoming entry point to the home.
Home in New Buffalo

Modern Farmhouse - Walk to Downtown, beach & pool!

4.96 out of 5 average rating, 108 reviews
Top guest favorite
The exterior of the cottage features vibrant blue siding and a covered porch with white railings. Lush greenery and landscaped beds surround the entrance, creating a serene and welcoming façade. A pathway leads to the front door, inviting guests into the home.
Home in New Buffalo

Designer Cottage - walking distance to downtown

5.0 out of 5 average rating, 220 reviews
Guest favorite
The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.
Home in Michigan City

5 Bedroom Luxury Home In Heart of Beachwalk Resort

4.96 out of 5 average rating, 206 reviews
Guest favorite
Home in Michigan City

Home near the lake with an inground pool

4.91 out of 5 average rating, 106 reviews
Top guest favorite
The exterior of a two-story home is visible, featuring a welcoming front entrance. A large tree provides shade, with a swing hanging from one of its sturdy branches. Ferns line the landscape, creating a natural border around the property, complemented by a well-maintained lawn.
Home in St. Joseph

4 Bedroom home w/pool in St. Joseph

5.0 out of 5 average rating, 117 reviews
Guest favorite
A modern living room features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, while two lamps provide soft lighting. Artwork adorns the wall above, accompanied by a round mirror reflecting the space.
Condo in New Buffalo

Nightingale Dunes - Modern beach town retreat

4.93 out of 5 average rating, 105 reviews
Superhost
A spacious, well-maintained heated pool features clear blue water and is framed by a clean deck. Sturdy pool steps are visible, providing easy access. Lounge chairs are placed around the pool's edge, and surrounding greenery adds a natural touch.
Tiny home in Sawyer

After Dune Delight in Sun Coast Park

4.78 out of 5 average rating, 161 reviews

When is the best time to visit Three Oaks?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$42,262 GYDG$42,890 GYDG$46,656 GYDG$46,656 GYDG$52,305 GYDG$57,954 GYDG$62,556 GYDG$61,092 GYDG$53,979 GYDG$48,330 GYDG$44,354 GYDG$44,354 GYD
Avg. temp-4°C-3°C3°C9°C15°C20°C22°C22°C18°C11°C4°C-1°C

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