Family-friendly vacation rentals in Three Oaks

4.99 out of 5 average rating, 522 reviews

A charming, rustic cabin is nestled among vibrant autumn foliage, showcasing a wooden exterior and a sloped metal roof. The cabin is partially obscured by trees, with golden leaves creating a warm frame around the structure, signaling a serene woodland retreat.

Farm stay in La Porte

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

4.97 out of 5 average rating, 194 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.

4.97 out of 5 average rating, 224 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. :)

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, 171 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!

4.82 out of 5 average rating, 748 reviews

An aerial view captures the inviting pool area surrounded by lush greenery. The sparkling blue pool is framed by several lounge chairs, with a shaded patio leading to a well-maintained RV parked near the entrance. Colorful landscaping adds to the serene outdoor setting.

Camper/RV in Porter

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Heated pool open until mid October! Hot tub open all year! Fully equipped RV sleeps 5, has bathroom w/shower, stove, microwave, TV, heat & A/C, & running water all year. Located on the bike trail & only minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hike in the Indiana Dunes National Park along the Little Calumet River & the historic Bailley homestead, only 1 block from the RV. Enjoy our large pool, hot tub, grill, campfire, & playground too. Schedule your visit today!

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, 191 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.

Guesthouse in New Buffalo

A compact guest house features a light green exterior with white trim, set within a grassy area. A welcoming front porch includes two chairs and a small bench, surrounded by flowering plants. Large windows allow ample natural light to enter.

4.98 out of 5 average rating, 888 reviews

"Tiny House" Guest House - No Cleaning Fee

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

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, 125 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

4.98 out of 5 average rating, 133 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!

4.93 out of 5 average rating, 192 reviews

A charming cabin is nestled among tall trees, with a deck visible on one side. Surrounding areas feature mowed grass and fallen leaves, creating a tranquil rural setting. Additional structures, including a shed, can be seen in the background, adding to the serene atmosphere of the property.

Guesthouse in Sawyer

Heron's Rest Hideaway, nature lovers' dream

Privacy on 11 acres of conservancy-protected land including two small lakes, river access , woods. Rowboat available. Minutes from Michigan’s most popular beach, breweries, wineries, antique malls, farm-to-table restaurants. Fully equipped kitchen, gas fireplace. Private fire pit, deck, and gas grill. Kayak, bike, hike nearby. Separated from our home by a breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible. Limit of 4 guests.

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, 635 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.

4.99 out of 5 average rating, 152 reviews

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!

Popular amenities for Three Oaks family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The exterior of the Oak St. Guest House showcases a two-story home with a welcoming front porch. Lush greenery surrounds the house, and a well-maintained walkway leads to the entrance. The driveway provides access to the garage, with trees and shrubs enhancing the inviting atmosphere.

4.97 out of 5 average rating, 118 reviews

Great Yard, HOT TUB, Steps from Downtown

4.8 out of 5 average rating, 116 reviews

An inviting backyard features a central fire pit surrounded by several metal chairs. The bi-level house is visible in the background, with large windows reflecting the evening light. A hot tub is seen nearby, framed by trees and a spacious lawn.

Apartment in Bridgman

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

4.96 out of 5 average rating, 259 reviews

A modern kitchen is visible, featuring white cabinetry and stainless steel appliances. The living area includes a comfortable couch and a round table with a decorative runner. Natural light fills the space, highlighting the open layout and ceiling beams.

Home in Lakeside

Couples alert! PVT beach access, hot tub, firepit!

5 out of 5 average rating, 231 reviews

The exterior of a circular, dark-hued building is illuminated by warm string lights during twilight. A private hot tub and a fire pit with chairs are visible, while the surrounding natural landscape emphasizes the peaceful setting.

Farm stay in Vandalia

Grain Binn | Hot Tub | Unique | 2 Baths | Lux

4.98 out of 5 average rating, 112 reviews

A clear, geodesic dome is set on a paved patio surrounded by a grassy area and decorative plants. The backdrop features a tranquil lake and lush trees, illuminated by a colorful sunset sky.

Guesthouse in Valparaiso

Unique Dome Retreat by Indiana Dunes w/ Lake View

An updated home is positioned at the center of the image, featuring a welcoming entrance with a decorative porch and large front steps. Surrounding gardens include well-maintained shrubs and trees. The sky showcases soft pink and purple hues as daylight transitions into evening.

5 out of 5 average rating, 104 reviews

Hot tub! In the heart of Three Oaks!

4.95 out of 5 average rating, 329 reviews

An inviting cottage exterior features a wooden fence and a screened porch. Surrounding greenery showcases tall grasses and autumn foliage, creating an appealing atmosphere. A chimney and part of the roof can be seen, indicating the cozy interior space.

Cottage in Union Pier

J’s Beach House: Hot Tub & short walk to beach!

Guest suite in Saint Joseph

A well-appointed kitchen and dining area are presented, featuring white cabinetry and essential appliances. A wooden dining table with six chairs invites gatherings, while ample natural light brightens the space through a nearby window. The warm-toned flooring complements the overall inviting ambiance.

4.87 out of 5 average rating, 238 reviews

Charming 2BR St Joseph Retreat Peaceful Setting

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 263 reviews

A charming farmhouse is surrounded by blooming pink magnolia trees, creating a serene setting. Two large windows are visible on the upper level, complemented by decorative latticework on the side. A vintage wheel and garden furniture hint at the inviting outdoor space.

Cottage in Sawyer

Northwind Llama retreat “Chicken coop”

Guesthouse in Sodus Township

A spacious outdoor view is presented from a deck, overlooking expansive green fields and wooden fencing. In the distance, a large barn is visible, along with a few horses grazing nearby. A tree branch frames the scene, creating a peaceful country atmosphere.

4.79 out of 5 average rating, 283 reviews

Farm Cottage

4.9 out of 5 average rating, 114 reviews

A wood-burning campfire is surrounded by stones, with two folding chairs positioned nearby. The rustic cabin features large windows and a green metal roof, with a porch area visible in the background. A heater stands next to the fire, providing warmth.

Farm stay in Galien

Off-The-Grid Camping Cabin on a Homestead Farm

4.86 out of 5 average rating, 105 reviews

A wooden sign displaying 'THE LOFT' is mounted on a post, set against a backdrop of a wooden fence with a natural finish. The area is surrounded by grass and scattered autumn leaves, adding a seasonal touch to the entrance.

Apartment in Niles

The Loft

4.8 out of 5 average rating, 255 reviews

A cozy space features a daybed with plush pillows and warm throws. Soft lighting is provided by pendant and string lights, while earthy wallpaper enhances the room's charm. A comfortable chair and a textured rug add to the welcoming ambiance.

Tiny home in Coloma

-Shingle Diggins Cottage-

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.

4.86 out of 5 average rating, 121 reviews

Walk downtown in Three Oaks Modern Victorian Home

4.94 out of 5 average rating, 100 reviews

A spacious living area features a deep red sofa with a striped throw, complemented by wooden floors and rustic beams. In the background, a queen bed is visible, flanked by framed artwork. Large windows allow natural light to illuminate the cozy interior.

Barn in South Bend

Charming Farm Retreat Awaits!

Luxe

An open entryway reveals a modern kitchen with a large island and four high stools. Natural light flows through multiple windows, highlighting the sleek countertops and rich cabinetry. A tasteful artwork adorns the wall beside the entrance, adding character to the space.

Home in Lakeside

4.93 out of 5 average rating, 111 reviews

Landmark Home 1 Blk from Lk MI w/Game Rm + EV Chgr

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 218 reviews

A private cottage is surrounded by lush greenery and features a wooden deck adorned with several blue planters. Steps lead up to the entrance, which is framed by large windows allowing natural light to fill the interior.

Guesthouse in Valparaiso

Private Cottage in Gated Nudist Community

4.89 out of 5 average rating, 139 reviews

A private pool area is framed by a white fence, featuring a clear blue pool surrounded by lounge chairs. Lush greenery and a large tree provide shade, while the serene view of Lake Chapin and distant trees is visible in the background.

Home in Berrien Springs

Lake House Retreat on the water

4.92 out of 5 average rating, 115 reviews

The exterior of a multi-level house is depicted, featuring a combination of siding and stone accents. Large windows are present, along with balconies on the upper levels. A paved driveway leads to a garage, surrounded by greenery and a clear blue sky.

Home in Michigan City

Beautiful home with Beach views in Beachwalk

4.96 out of 5 average rating, 184 reviews

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

4.94 out of 5 average rating, 164 reviews

A private hot tub is set in a wooden enclosure, surrounded by a serene natural landscape. Steps lead up to the hot tub, offering easy access. Two white Adirondack chairs are positioned nearby, inviting relaxation in the peaceful outdoor setting.

Home in Union Pier

Winter & Holiday Couples getaway Pvt Hot tub

4.98 out of 5 average rating, 173 reviews

A fenced-in pool area features a clear water pool surrounded by a concrete deck. Lounge chairs and a dining set are positioned nearby, while a red umbrella offers shade. A slide is visible in the pool, with cornfields extending in the background under a cloudy sky.

Guesthouse in Cassopolis

Couples cottage with hot tub!

4.97 out of 5 average rating, 126 reviews

An aerial view showcases the spacious outdoor area, featuring a blue tennis court adjacent to a rectangular pool surrounded by lounge chairs. Lush greenery and trees frame the property, while a well-maintained lawn offers additional recreational space.

Villa in Niles

Pool, Hot tub, Kayaks, Waterfront, SW Michigan