Family-friendly holiday rentals in Benton Harbor

Four wooden chairs are positioned on a deck overlooking Lake Michigan. The sun is rising in the sky, creating a shimmering reflection on the water's surface. Trees frame the scene, adding a touch of greenery to the picturesque view.

4.98 out of 5 average rating, 221 reviews

Lake Michigan Views | Mins. to St. Joe | Hot tub

🌊 Spectacular Lake Michigan views 🌅 Deck overlooking Lake Michigan 🔥 Year-round, private hot tub 🌞 Beach necessitates included 📍 Minutes to downtown St. Joe & Silver Beach 🏖️ 5 Lake Michigan beaches within 5 miles 🌳 Private, quiet setting with outdoor seating ✨ Magical fire pit space ⛳️ Near Harbor Shores Golf Course 🛏️ King bed ♾️ Infinity gaming table ⭐️ Top rated home in St. Joe ☕️ Complimentary coffee & tea- Keurig duo 🧑‍🍳 Fully stocked kitchen ⚡️ High speed internet 🧺 Washer

Indoor spacesFamilyLaundry

4.85 out of 5 average rating, 128 reviews

A welcoming porch is featured, showcasing a comfortable seating area with a navy blue cushion sofa and two matching chairs. Lush greenery surrounds the entrance, and natural light illuminates the space through large windows.

Home in St. Joseph

Silver Beach 2bd -1 block to downtown State Street

The historic McNeil House is located on State Street just one block from Downtown restaurants, shops, and the Bluff. You won't find a better or more convenient location when visiting this beautiful city! We're offering smaller groups an opportunity to stay in our historic home by renting the main floor that sleeps up to five guests. The upstairs will not be rented during your stay, so you'll have the house to yourself but won't have access to the upstairs. Only available during the off season.

Indoor spacesFamilySleep quality

Guest house in Benton Harbor

A charming green cottage is nestled among trees, surrounded by well-kept landscaping and flower pots. A red umbrella shades a picnic table nearby, creating a welcoming outdoor space. The gravel path leads to the cottage entrance, framed by large windows for natural light.

4.94 out of 5 average rating, 207 reviews

Cozy Green Cottage with Private Beach

Cozy cottage hidden away in a quiet neighborhood 1.5 blocks from Lake Michigan, featuring a screened back porch perfect for morning coffee. Near the Benton Harbor Arts District, downtown St Joe, this cottage is surrounded by local restaurants, breweries, wineries, golf courses and shops. The beach is a year round destination, each season has its own wonders. Note: no TV, and WiFi can be spotty due to hills. Expect 90+ tiered steps to the sandy beach below. AC upstairs, original claw footed tub.

FamilyKitchenAir conditioning

4.94 out of 5 average rating, 232 reviews

A cozy living room is featured with a soft beige sofa and an armchair in navy blue. A light rug with earthy tones is placed under a white coffee table, which holds magazines. A fireplace is surrounded by decorative mirrors, enhancing the welcoming environment.

Cottage in Stevensville

Cheerful Stevensville cottage, GREAT LOCATION!

Right in the prettiest area of Stevensville, Glenlord Cottage is an ideal location for your Southwest Michigan stay. Down the road you will find Glenlord Beach Park, a beautiful Lake Michigan overlook. Around the corner, an award-winning bakery. In Stevensville with its variety of restaurants, beaches, and shops, Glenlord Cottage is also within easy reach of many SW Michigan attractions and is well placed for visits to wineries, golf courses, and downtown St. Joseph with its shops and festivals.

FamilyKitchenAir conditioning

A modern kitchen features white cabinetry and light gray marble countertops. An indoor plant is positioned prominently at the center, adding a touch of greenery. Behind it, stainless steel appliances and decorative tiles provide a subtle backdrop, while natural light enhances the open atmosphere.

4.93 out of 5 average rating, 104 reviews

Be Our Guests: Harbor Shores Comfort Meets Charm

Newly renovated home with enormous backyard, large new patio, and a newly constructed deck for morning coffee and tea. You will find all of the amenities of home and more! Centrally located to many local beaches, all within a 6 minute drive. Trails to walk and bike paths abound as Harbor Shores golf course is one block away. A fantastic brewery and sister restaurant with an amazing burger are within walking distance too. Please let us know how we can make your stay amazing. Be our guests!

FamilyIndoor spacesBathroom

4.98 out of 5 average rating, 119 reviews

Cabin in Coloma

Cozy Cabin in the Woods

Just under two hours from Chicago and only 1/2 mile from Hagar Beach, this beautifully updated 100-year-old cabin offers a peaceful retreat in the woods. Surrounded by tranquil landscapes and towering trees, you’ll enjoy the perfect blend of rustic charm and modern comfort. Tucked along a quiet dirt road, the cabin is ideally located 15 minutes from South Haven and 10 minutes from St. Joseph making it close enough for dining, shopping, and activities, yet far enough to unwind in nature’s calm.

Indoor spacesFamilyHospitality

4.92 out of 5 average rating, 225 reviews

A cozy living area features exposed brick walls and large windows allowing natural light to fill the room. A dark sectional sofa contrasts with a patterned armchair, while a coffee table displays a decorative flower and various items. Warm hardwood floors enhance the inviting atmosphere.

Loft in Benton Harbor

Romantic Gastro Loft Retreat for Two

Located above the area’s hottest new restaurant, this newly renovated 1BR/1BA urban loft features classic finishes - exposed brick, high ceilings, maple floors, and quartz countertops. Cozy, comfortable quarters directly above the Houndstooth restaurant provide a fantastic opportunity to get a “taste” of the Benton Harbor Arts District. Muffled sounds of music and activity from the restaurant below are often present in the loft during evening hours. Some guests may find this objectionable.

Indoor spacesFamilyTV

The beach at The Windover features soft, sandy shores with gentle waves lapping at the water's edge. The cottage, showcasing a modern design, stands nearby with large windows and a welcoming porch. A seating area adorned with a candle and flowers offers a perfect spot to relax.

4.99 out of 5 average rating, 188 reviews

Panoramic Views/Beach/Hot Tub/Sauna/Cold Plunge

Welcome The Windover! • Private Beach • Panoramic Lake Michigan Views • Hot Tub, Sauna, Cold Plunge, Outdoor Shower •Expansive Yard /Outside Activities • 4 minutes to downtown St. Joseph, The Benton Harbor Arts District, and Harbor Shores • Centrally located Close to 6 Local Beaches Fine and Casual Dining World Class Golfing Wineries Breweries Nature Parks Mountain Bike Trail Park 1/4 from Property Curious Kids Museum Compass Fountain Silver Beach Carousel St. Joseph Lighthouse

FamilyIndoor spacesCondition

4.92 out of 5 average rating, 151 reviews

The exterior of a modern tiny house is seen surrounded by trees. Soft lighting strings hang above a fire pit with four Adirondack chairs arranged around it. Smoke rises from a fire, creating a cozy outdoor space.

Tiny home in Sawyer

Modern Minimalist Tiny House | Firepit | Nature

Welcome to our modern minimalist tiny house located a half mile from Warren Dunes State Park beach and 1.5 miles from all that Sawyer Michigan area has to offer. Tiny is the second dwelling on this property and is technically a mobile tiny house. While we do have electricity and water, much like an RV the drains run to holding tanks. This means VERY LIMITED WATER USE for showers and toilet flushing. It features a fully stocked kitchen, bathroom, and a queen bed in the small loft.

FamilyKitchenWifi

4.86 out of 5 average rating, 172 reviews

Cottage in Benton Harbor

Hot tub! Blue Bird Cottage of Harbor Country!

The Blue bird is located in a revitalizing part of Benton Harbor close to Harbor Shores golf course and all of the action of downtown St. Joseph, Benton Harbor Arts district and the beach! Enjoy grilling out after the beach, watching a movie on our 120” projection movie theater, or catching up around the firepit and 2-person hot tub. Blue Bird is 1 mile from one of the best beaches in the region, Jean Klock beach, and a short drive to award-winning beaches, wineries & restaurants!

FamilyKitchenAccuracy

4.95 out of 5 average rating, 150 reviews

Flat in Benton Harbor

Cozy apartment minutes from lake

Enjoy your stay in a cozy, yet spacious apartment. Full bath tub for warm baths during the chilly season and shower to wash sand off your feet from trips to the beach only 9 minutes away. You can relax on the couch & watch Netflix, enjoy a warm beverage with your guests around the table or lounge in your own Queen-sized bed. There are many options for casual & fine dining, shopping, walking trails, enjoying stunning sunsets at Lake Michigan & wine tours just minutes away.

FamilyKitchenNearby

5.0 out of 5 average rating, 212 reviews

Barn in Stevensville

The Blue Barn - A cozy country getaway!

Welcome to “Blue Barn” vacation home, a country retreat located between beautiful St. Joseph beaches and several Baroda wineries. A welcoming, open floor plan makes it easy for your group to spend time together. Enjoy the crisp white bedding, fully stocked coffee and wine bar, and private fire pit to unwind with friends and family. Grand Mere State Park, Weko Beach, and several local breweries are all just a short drive from this ideally located property.

FamilyIndoor spacesAir conditioning

Popular amenities for Benton Harbor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.9 out of 5 average rating, 253 reviews

A well-maintained single-story home is seen alongside a spacious driveway leading to a two-car garage. The home features a charming front porch and neatly landscaped yard, with green grass surrounding the property and trees lining the background.

Cottage in Benton Harbor

Cottage near Hagar Beach Pet friendly with Hot tub

FamilyIndoor spacesBathroom

4.92 out of 5 average rating, 891 reviews

A garden pathway leads from the house to the beach, surrounded by lush trees and colorful blooms. A charcoal grill is visible on the patio, and gray steps ascend towards the entrance. The tranquil Lake Michigan is seen in the background through the foliage.

Flat in Stevensville

Quiet Grand Mere Coach House on Lake Michigan

KitchenIndoor spacesCheckout

4.98 out of 5 average rating, 105 reviews

The exterior of the lake house features a multi-level design with a spacious patio area, highlighted by a fire pit surrounded by stone borders. A hot tub sits nearby, and comfortable seating is arranged under a covered balcony. Lush greenery provides a serene backdrop.

Cottage in Benton Harbor

Cheerful Sister Lakes 4 BDR Lake Hse w/ Hot tub.

KitchenFamilyHospitality

4.96 out of 5 average rating, 100 reviews

Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

FamilyKitchenHeating

4.97 out of 5 average rating, 288 reviews

An inviting hot tub is positioned outdoors, surrounded by lush greenery. A wooden privacy screen adds to the tranquility, while an outdoor shower with modern fixtures is nearby. The patio area is designed for relaxation, creating a soothing space for unwinding.

Home in South Haven

Family Friendly Private Beach Home with Hot Tub

FamilyIndoor spacesHospitality

Superhost

4.84 out of 5 average rating, 101 reviews

Serenity House on the River

Indoor spacesKitchenCondition

4.97 out of 5 average rating, 246 reviews

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

FamilyIndoor spacesSleep quality

4.94 out of 5 average rating, 111 reviews

Home in Stevensville

A-frame • Hot Tub • Fire Pit • Wineries • Beach

Indoor spacesKitchenComfort

Family- and pet-friendly home rentals

A ranch-style house is presented, featuring a welcoming front porch with two chairs. Colorful flowerpots and vibrant blooms adorn the entrance, complemented by a neat lawn. The exterior showcases a blend of subtle hues, highlighting the inviting atmosphere of the home.

4.87 out of 5 average rating, 134 reviews

2 mins from beach/monthly stays available

KitchenIndoor spacesAccuracy

Guest house 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.

4.83 out of 5 average rating, 367 reviews

Farm Cottage

Indoor spacesKitchenParks

4.95 out of 5 average rating, 132 reviews

Home in Buchanan

-The District 5 Schoolhouse-

FamilyIndoor spacesCleanliness

4.9 out of 5 average rating, 105 reviews

A single-story country retreat features a blend of blue siding and stone accents. The well-maintained lawn is complemented by colorful landscaping. Large windows reflect natural light, enhancing the inviting exterior. A garage door provides additional functionality, while clouds drift peacefully overhead.

Flat in Benton Harbor

Wine Country Retreat near St. Joseph, Michigan

FamilyKitchenWifi

Guest house in Stevensville

The exterior of the converted barn is shown, featuring a rustic red facade with multiple windows on the upper level. Lush green grass and large decorative plants frame the building, while a charcoal grill is positioned on a patio area, providing space for outdoor gatherings.

4.98 out of 5 average rating, 337 reviews

Red Barn Lodge

FamilyKitchenBiking

Superhost

Cabin in Watervliet

4.92 out of 5 average rating, 402 reviews

Riverview Cabin

FamilyIndoor spacesAir conditioning

4.96 out of 5 average rating, 116 reviews

The A-frame cottage is nestled among tall trees, featuring a blend of stone and wood in its design. Large glass windows create a connection with nature, inviting natural light into the living spaces. A pathway leads toward the entrance, surrounded by lush greenery.

Cabin in Stevensville

Idyllic A-frame in Michigan’s Harbor Wine Country

KitchenIndoor spacesCleanliness

4.98 out of 5 average rating, 137 reviews

A spacious house exterior is presented, featuring a light grey facade with white trim. Sturdy steps lead up to the front entrance, which is flanked by large windows. A well-maintained lawn surrounds the property, and clear blue skies are visible above.

Home in Stevensville

Grand Mere Guest House | Stevensville

FamilyIndoor spacesBeach

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 109 reviews

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

KitchenIndoor spacesView

4.97 out of 5 average rating, 134 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

FamilyKitchenPets

4.9 out of 5 average rating, 152 reviews

Home in Bridgman

Indoor Heated Pool | Hot Tub | Near Beaches

Indoor spacesKitchenGetting around

5.0 out of 5 average rating, 249 reviews

The exterior of a two-story gray and green house is showcased, featuring a stone-accented garage and white-trimmed windows. Lush shrubs line the entrance, and a gravel driveway leads to the garage, set against a backdrop of greenery and a clear blue sky.

Home in South Haven

Driftwood Shores-SH is a great fall getaway!

FamilyIndoor spacesHospitality

4.91 out of 5 average rating, 132 reviews

A blue cottage is surrounded by tall trees, featuring large windows that provide ample natural light. A spacious deck extends around the front, with steps leading to the entrance. A chimney is visible on the side, adding to the cottage's charm.

Cottage in Sawyer

The Cranny at Michaels Nook

FamilyKitchenOutdoor spaces

Superhost

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.

Home in Three Oaks

4.84 out of 5 average rating, 109 reviews

Play @ The Hideaway - hot tub, sauna, gymnasium

KitchenIndoor spacesAccess

Guest house in Cassopolis

An aerial view showcases a fenced-in pool area surrounded by lush green lawns and mature trees. A small patio with outdoor seating is visible beside the pool. The gravel driveway leads to the property, with an adjacent structure and a pergola enhancing the outdoor space.

4.98 out of 5 average rating, 202 reviews

Studio apartment for two with pool & hot tub!

Indoor spacesKitchenCondition