House holiday rentals in Three Oaks

4.83 out of 5 average rating, 128 reviews

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.

LocationFamilyBarbecue

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.

4.94 out of 5 average rating, 106 reviews

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!

ValueLocationGetting around

4.96 out of 5 average rating, 279 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. :)

LocationFamilyComfort

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.

4.97 out of 5 average rating, 245 reviews

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.

ValueFamilyAmenities

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, 193 reviews

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!

ValueFamilyBarbecue

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.

4.87 out of 5 average rating, 134 reviews

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!

FamilyValueBackyard

5.0 out of 5 average rating, 150 reviews

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

Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

ValueFamilyComfort

4.97 out of 5 average rating, 127 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!

FamilyValueBiking

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, 151 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

LocationFamilyWi-Fi

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.

5.0 out of 5 average rating, 111 reviews

In the heart of Three Oaks! Hot tub!

Enjoy the splendor of Michigan's Harbor Country! Our updated home is 1 block from the main street (Elm)& walkable to everything! Enjoy specialty boutiques,antiques, restaurants, bakeries, & event venues including Journeyman Distillery, Acorn (music venue) & Vickers Theater. It’s a short 10 minute drive to Lake Michigan! The friendly village of Three Oaks is the perfect place to kick back, relax, & enjoy small town living! The movie Prancer was filmed here! airbnb.com/h/7linden

ValueFamilyKitchen

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, 159 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!

ValueFamilyComfort

5.0 out of 5 average rating, 119 reviews

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.

ValueLocationGetting around

Popular amenities for Three Oaks house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious outdoor area features a hot tub beside a well-maintained pool. Lounge chairs are positioned around the pool, with a covered seating area in the back. A wooden pergola provides shade, while string lights add a touch of ambiance.

4.85 out of 5 average rating, 110 reviews

Play @ The Hideaway - hot tub, sauna, gymnasium

LocationFamilyParking

4.97 out of 5 average rating, 100 reviews

An inviting pool area is surrounded by a wooden deck, featuring comfortable seating arrangements and a large red umbrella providing shade. Lush greenery stands tall in the background, complementing the serene atmosphere of the private fenced space.

Home in Lakeside

Lakeside with heated pool & pvt beach access!

FamilyLocationParks

4.96 out of 5 average rating, 102 reviews

Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

LocationFamilyBackyard

4.99 out of 5 average rating, 109 reviews

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

FamilyValueWi-Fi

4.94 out of 5 average rating, 184 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

New Hot tub Heated Pool Union Pier

FamilyLocationQuiet

A private pool is surrounded by a spacious patio, featuring lounge chairs for relaxation. The area is enclosed by a wooden fence, offering privacy, and a storage shed is visible in the background, complemented by a lush green landscape.

4.83 out of 5 average rating, 102 reviews

Secluded Pool Playhouse: Hot Tub, Game Room, Fire

ValueFamilyTV

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.

5.0 out of 5 average rating, 214 reviews

Designer Cottage - walking distance to downtown

ValueFamilyCheck-in

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.

4.96 out of 5 average rating, 107 reviews

Modern Farmhouse - Walk to Downtown, beach & pool!

LocationFamilyBarbecue

Weekly house rentals

4.95 out of 5 average rating, 135 reviews

Home in Buchanan

-The District 5 Schoolhouse-

ValueLocationView

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

4.92 out of 5 average rating, 119 reviews

Landmark Home 1 Blk from Lake MI Game Rm & EV Chgr

LocationValueLayout

A spacious backyard is enclosed by wooden fencing, featuring a green lawn, a sandbox for children, and a colorful outdoor mural on the shed. A seating area with patio furniture is visible, complemented by landscaped flower beds. The sky is bright with scattered clouds.

4.97 out of 5 average rating, 210 reviews

In-town Lovely Home! Steps to Starbucks & Beach!

FamilyLocationSleep quality

4.95 out of 5 average rating, 330 reviews

The modern tree-house structure is illuminated by warm lighting, showcasing large windows that reflect the surrounding trees. A screened porch with seating is visible, extending from the main building, creating a connection with nature.

Home in Michigan City

TRYON FARM MID-MODERN SPA IN THE WOODS

LocationFamilyBiking

A warmly lit living room displays a comfortable sectional sofa paired with an accent chair. A coffee table sits in front, surrounded by a woven rug. Natural light enters through window panels, and a welcome sign is visible near the entrance, enhancing the inviting ambiance.

4.94 out of 5 average rating, 115 reviews

Ash & Elm • Your Home Away From Home!

ValueLocationCheck-in

4.99 out of 5 average rating, 164 reviews

The exterior of the cozy Tree House is highlighted, featuring a spacious deck with rocking chairs. Mature trees surround the cottage, which showcases a warm exterior design. A well-maintained garden with shrubs and decorative plants enhances the inviting atmosphere.

Home in Lakeside

Lakeside Retreat Nestled Among the Trees

LocationFamilyLayout

4.93 out of 5 average rating, 165 reviews

A comfortable living area features a dark gray sectional sofa adorned with yellow and patterned throw pillows. A light wood coffee table sits in front, with a remote control resting upon it. Natural light filters through sheer curtains, illuminating the space adorned with framed artwork.

Home in Sawyer

Charming Downtown Sawyer Home Close to the Dunes

LocationValueCleanliness

4.96 out of 5 average rating, 117 reviews

A modern cabin nestled among mature trees is illuminated softly at dusk. Lush landscaping includes decorative grasses that glow warmly, while large windows reveal inviting interior spaces. Stone steps lead up to the entrance, enhancing the natural setting.

Home in Union Pier

The sanctuary with hot tub, 15 min walk to beach !

LocationFamilyHospitality

Private house rentals

5.0 out of 5 average rating, 30 reviews

Butternut House

FamilyLocationWalkability

4.95 out of 5 average rating, 21 reviews

A light-filled living area is characterized by high ceilings and large windows offering views of the outdoors. Soft beige furniture surrounds a round coffee table, while neutral tones create a calming environment. Decorative plants and art enhance the minimalist design, inviting relaxation.

Home in Union Pier

Designer home in Union Pier: steps to deeded beach

FamilyValueCondition

A charming farmhouse features a two-story white exterior with a triangular roof. A welcoming porch includes two rocking chairs and a small table with flowers. An orange pumpkin adds seasonal decor, while a Coca-Cola cooler is placed beside the door.

5.0 out of 5 average rating, 50 reviews

Three Oaks Farmhouse, Sleeps 12 in 4 Bedrooms

FamilyLocationBackyard

The exterior of a charming two-story home is displayed, featuring a peaked roof and front porch with white railings. Lush green landscaping surrounds the property, while large shrubs and decorative trees add to the inviting atmosphere. Bright blue skies complement the home's color.

4.98 out of 5 average rating, 60 reviews

Three Oaks Inn, Groups of 14+ (Near Journeyman!)

FamilyLocationCheck-in

A spacious living area features a cozy seating arrangement with a light brown sofa and modern chairs. The room includes a coffee table atop a decorative rug, an electric fireplace, and a television. Natural light streams through the windows, illuminating the calming color palette.

4.9 out of 5 average rating, 40 reviews

Oasis in the Oaks

FamilyLocationCleanliness

A spacious outdoor area features a fire pit surrounded by six light-colored chairs, providing a cozy gathering space. A green shed stands adjacent to the stylish dark wood home, which is complemented by grass and tree coverage, creating a pleasant social setting.

4.96 out of 5 average rating, 50 reviews

Irish Spring in Three Oaks

FamilyLocationDecor

A living room area is depicted featuring hardwood flooring and a striped area rug. A dark blue cabinet supports a flat-screen television. Nearby, potted plants add greenery to the space, while a light curtain allows natural light to filter in through the window.

4.93 out of 5 average rating, 90 reviews

Catalina's Place in Downtown T.O. ~ 4BR / 1.5BA

ValueFamilyQuiet

A two-story light blue house is framed by lush green trees. Soft illumination is visible through the windows, enhancing the home's inviting appearance. A covered porch extends across the front, providing easy access to the entrance. Neatly trimmed bushes and flowers are arranged in the yard.