Family-friendly holiday rentals in Benton Harbor

Guesthouse 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, 209 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.

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, 226 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

4.85 out of 5 average rating, 129 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.

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, 106 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!

A cozy living area features a plush gray sectional sofa with blue accent pillows, paired with a round coffee table on a soft area rug. Natural light enters through two windows adorned with dark curtains, and a television is mounted on the wall opposite a wooden media console.

4.92 out of 5 average rating, 138 reviews

The Hanger Hideout | Airplane Mode

Welcome to our charming retreat nestled in the heart of Southwest Michigan! Our cozy home is located just a stone throw away from the shores of Lake Michigan, offering sunsets and serene beach strolls. Golf courses are near in distance, while wine tasters can savor the region's renowned vineyards and enjoy delightful wine tastings. With a perfect blend of natural beauty, outdoor adventures, and culinary delights, our Airbnb is the idyllic haven for your unforgettable Southwest Michigan getaway.

5.0 out of 5 average rating, 113 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

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

A charming lake cottage is showcased, featuring a light-colored exterior and large windows that invite natural light. A welcoming front deck is visible, with steps leading down to a landscaped yard and the surrounding greenery, enhancing the serene outdoor environment.

4.99 out of 5 average rating, 191 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

4.9 out of 5 average rating, 255 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

•Brand New Nordic Hot Tub• •September 2023 • Gather with family or meet with friends, there's plenty of room to stay the weekend. The inside of the home has refinished hardwood flooring throughout from the 1930's. The entire home is newly renovated giving it a classic Lake Michigan vibe. Only a few hundred feet from Lake Michigan's shoreline and one mile to pet friendly Hagar Park, there's a playground for the kids and plenty of beach to lay around on and enjoy with family and pet's.

4.86 out of 5 average rating, 174 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!

5.0 out of 5 average rating, 216 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.

4.99 out of 5 average rating, 289 reviews

A charming cabin exterior is framed by lush greenery, with a sloped roof and log-style siding. Red accents on the window frames add warmth. A stone pathway leads to an inviting seating area with wooden chairs, surrounded by colorful flower beds and native plants.

Cabin in Benton Harbor

Charming Cabin-Private Beach & Golf

Why the rave reviews? This cabin is a unique and charming 2 bedroom retreat that sits atop a hill and is surrounded by elegantly sculpted terrain of Harbor Shores golf course and walking trails. The private beach on Lake Michigan is steps away. It is located in a quiet neighborhood and is close to family fun activities in St. Joe/Benton Harbor, fantastic restaurants, wine tasting, art galleries and quaint shops.

Guesthouse in Stevensville

An inviting kitchen features wooden cabinetry and granite countertops. A black 'welcome' sign is placed on the countertop next to a vase of fresh flowers. Kitchen appliances, including a coffee maker, are neatly arranged, creating a functional and welcoming space.

4.99 out of 5 average rating, 274 reviews

The Shire

Nestled on five secluded, tree-lined acres, with a pond, waterfall, fire pit, tree swing, basketball court and walking trails, The Shire feels a million miles away from it all - but isn't! We are only minutes away from wineries, breweries, amazing beaches, restaurants and shopping. (Notre Dame is an easy 30 minute drive). Southwest Michigan is a beautiful place to live! We'd LOVE to share it with you.

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

Superhost

4.84 out of 5 average rating, 103 reviews

Serenity House on the River

4.98 out of 5 average rating, 106 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.

4.96 out of 5 average rating, 102 reviews

Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

4.97 out of 5 average rating, 247 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

4.97 out of 5 average rating, 116 reviews

An outdoor area features a hot tub with illuminated turquoise water, surrounded by a patio adorned with string lights. The modern house showcases large windows, providing ample natural light, and a dining area with a table and chairs set under a nearby umbrella.

Home in Stevensville

Family Fun House: Hot Tub*Ping Pong*Nintendo*Fire

4.97 out of 5 average rating, 202 reviews

The exterior view showcases a modern lodge-style home with dark wood paneling and large windows. A pathway leads toward the entrance, bordered by greenery. Soft lights illuminate the building, creating a warm ambiance against a backdrop of trees.

Home in Union Pier

luxe new buffalo lodge, hot tub, 12m walk to beach

Apartment in Stevensville

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.

4.92 out of 5 average rating, 895 reviews

Quiet Grand Mere Coach House on Lake Michigan

4.94 out of 5 average rating, 168 reviews

A spacious deck surrounds a hot tub, with comfortable loungers positioned nearby. In the background, lush greenery frames an open field, and a wooden bridge spans a small area, enhancing the natural setting of the property.

Home in Berrien Springs

18-acre pond retreat | Heated pool & hot tub

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, 136 reviews

Special pricing tonight only!

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.

4.83 out of 5 average rating, 376 reviews

Farm Cottage

4.96 out of 5 average rating, 118 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

Apartment in Benton Harbor

4.94 out of 5 average rating, 156 reviews

Cozy apartment minutes from lake

4.95 out of 5 average rating, 101 reviews

A charming cottage is surrounded by a lush green lawn, featuring white Adirondack chairs positioned around a fire pit. The cottage, with its blue exterior, has multiple windows that invite natural light. Trees dot the landscape, creating a serene, secluded environment.

Home in Coloma

Dog-Friendly Lake-View Cottage Near Wineries

Apartment in Benton Harbor

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.

4.91 out of 5 average rating, 108 reviews

Wine Country Retreat near St. Joseph, Michigan

4.87 out of 5 average rating, 207 reviews

The cottage features a welcoming facade with blue shutters and a vibrant red front door. A decorative flag is displayed on the porch railing, surrounded by neatly manicured greenery and blooming flowers, contributing to the inviting outdoor space.

Home in Stevensville

Cheerful 3BR 2BA Country Cottage Near Attractions

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

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 252 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!

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

4.91 out of 5 average rating, 394 reviews

Cabin in Benton Harbor

Cozy Cabin

4.96 out of 5 average rating, 203 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

4.97 out of 5 average rating, 159 reviews

A private, heated pool is surrounded by a spacious patio, furnished with multiple lounge chairs. The two-story home features a balcony overlooking the pool area, with lush greenery framing the serene outdoor setting.

Home in South Haven

Private Pool 5 Minutes From Lake Michigan

4.84 out of 5 average rating, 202 reviews

A secluded in-ground pool is surrounded by lush greenery and landscaped gardens. Several lounge chairs are arranged near the pool, which reflects the sky above. Flowering plants and shrubs frame the scene, creating a peaceful outdoor retreat.

Home in South Haven

Experience Nature-Charming Cottage

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

4.85 out of 5 average rating, 110 reviews

Play @ The Hideaway - hot tub, sauna, gymnasium