Family-friendly holiday rentals in Benton Harbor

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.

4.84 out of 5 average rating, 152 reviews

A bright bouquet of sunflowers is displayed in a vase on a table, adding a touch of color to the room. Sunlight filters through large bay windows, illuminating the exposed brick walls and highlighting a cozy seating area with a red couch and wooden table.

Loft in Benton Harbor

Windy City Suite At The Stewart

Enjoy the best view of the Arts District perched high above the streets below with 180 degree views from the bay windows. Sleep in tranquility in the soft king size bed in the master bedroom. Cook a classic continental breakfast of scrambled eggs, bacon or waffles (provided) or grab one of the best breakfasts around at Mason Jar or coffee at Forte Coffee! Walk to The Livery, Houndstooth Restaurant, Larks BBQ, Pipestone Indoor Golf or Harbor Shores Golf Course too! Industrial, elegant, romantic.

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.

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.

4.79 out of 5 average rating, 283 reviews

Farm Cottage

Sweet cottage on our farm: Fully equipped kitchen and furnished living/sleeping area 14’x15' approx., washer/dryer. Sleeps 4: queen bed and queen sofa bed. Lots of privacy and next to organic garden, fields, stable and fruit orchards. All utilities, TV and WI-FI included. Well water with new water softener and water heater. Pet friendly; no pet fee. Lots of farm paths to walk your pet. Encourage off leash if trained. Horses have moved to another farm while pasture and stable rehabbed.

4.8 out of 5 average rating, 115 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.

Flat in Bridgman

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

Welcome to "Lake 2 Grapes" Bridgman is a little gem located between St. Joe and Warren Dunes. Minutes to Lake Mi. beaches, craft breweries, and wine trails. Relax in the upper level of our bi-level vacation home w/private entrance. This 3 bedroom, 2 bath includes a beautiful Master suite! Enjoy the Hot tub and fire pit in the backyard. Wine Tour? Stay with us and you'll receive a discount with "Grape & Grain Tours" plus complimentary pick up and drop off. Must be 25 or older to book.

4.91 out of 5 average rating, 360 reviews

An open living area features exposed brick walls, large windows allowing natural light, and a cozy gray sofa facing a low wooden coffee table. A decorative globe and a tall plant add character, while shiny hardwood floors enhance the space.

Loft in Benton Harbor

The Candy Loft in Arts District - 1BR/1.5BA Luxury

Welcome to The Candy Loft in Benton Harbor's Arts District! This 1BR/1.5BA condo boasts exposed brick, a king bed, and an oversized river rock shower in a spa-like bathroom illuminated by a skylight. The chef’s kitchen features a luxe Kitchenaid gas range, and an air mattress adds extra sleeping space. Housed in a historic candy factory, with an office in a former elevator shaft, it’s walking distance to restaurants, a brewery, and a coffee shop. Note: on the 2nd floor, stairs required.

4.96 out of 5 average rating, 528 reviews

A serene riverside view captures vibrant autumn foliage reflected in calm waters. Comfortable seating is arranged on a stone patio, overlooking the river, enhancing the tranquil outdoor experience. Sunlight dances on the water's surface, inviting relaxation and connection with nature.

Flat in Mishawaka

Private Entrance Guest Suite on the River

Stay in our studio apartment suite with private exterior door entrance. Hosts live in the rest of the house. From the backyard you can fish, kayak/canoe, paddle board, enjoy a bonfire, grill, and relax by the river. There's a king memory foam bed, sleeper sofa, and 49" TV. Remote work friendly with spacious workspace desk, fast WIFI, and coffee. The closet has a mini food prep area with mini fridge and microwave, and grill out on back patio. It's a quick 15 min drive to Notre Dame.

Guest house 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, 887 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.

4.93 out of 5 average rating, 102 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.

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

Beautiful two bedroom apartment with private access sitting in a scenic country setting nestled in vineyards and overlooking the valley. The kitchen includes a dw, range & fridge. Bedroom 1 has a queen bed while bedroom 2 has two single beds providing sleeping space for 4. The bath includes a tub/shower. The living space provides furniture for sitting or watching TV. There is also a washer and dryer. Should also note that this is a lower level suite with stairs to access.

4.99 out of 5 average rating, 177 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.

4.87 out of 5 average rating, 123 reviews

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.

Home in Benton Harbor

2 mins from beach/monthly stays available

1200 sq ft ranch style house w 2 bedrooms, 1 bath. Main bedroom has 1 queen size bed, 2nd bedroom has twin size bunk beds w twin size rollaway bed which enables a total of 5 guests. Appliances available for use are stackable washer/dryer, fridge, stove, over the range microwave, and dishwasher. Newer propane grill is available for use. *bunk bed will be difficult for older individuals due to lower bunk being low.

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

4.97 out of 5 average rating, 180 reviews

A year-round hot tub is set against a backdrop of lush greenery, with gentle water jets creating a soothing ambiance. String lights cast a warm glow above, complementing the evening sky as it transitions to dusk. Comfortable seating is arranged nearby for relaxation.

Home in Benton Harbor

Lake MI views: King bed: Mins to St. Joe: Hot tub

4.99 out of 5 average rating, 118 reviews

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

4.95 out of 5 average rating, 187 reviews

A fire pit surrounded by six chairs is set in a pebbled area, with a spacious yard and a blue house in the background. The house features a deck with seating and is framed by trees, creating a secluded atmosphere.

Home in Sawyer

Darling Home + Hot Tub by Warren Dunes + Wine Bar

5 out of 5 average rating, 230 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

4.89 out of 5 average rating, 228 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

4.98 out of 5 average rating, 124 reviews

A tranquil scene showcasing the serene waters of Lake Michigan, framed by lush greenery. The image features a private beach area with sand and a flag gently waving. A gazebo and seating around a fire pit highlight the outdoor living space, perfect for relaxation.

Home in Benton Harbor

Lake Michigan•Private Beach•Amazing View•Hot Tub

4.97 out of 5 average rating, 162 reviews

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 Sawyer

Hot tub open year round in modern/rustic cottage!

4.97 out of 5 average rating, 209 reviews

A cozy firepit area is surrounded by five Adirondack chairs arranged on a gravel-strewn surface. Neatly stacked firewood is visible in the background, shaded by lush greenery and trees, creating a peaceful outdoor retreat.

Home in Sawyer

Family Getaway with Year Round Hot Tub!

Family- and pet-friendly home rentals

4.82 out of 5 average rating, 345 reviews

A multi-level house is set on a grassy area, featuring a stairway leading to a deck adorned with flower pots. Vibrant red canopies provide shade, and bicycles are stationed nearby, creating an inviting environment. The exterior showcases a mix of wooden and painted surfaces.

Home in Chesterton

South Shore Studio Apartment {National Park}

Guest house in Near Northwest

The front porch of the cottage features a welcoming entrance with a red door. Two seating areas are situated on the porch, complemented by colorful flower pots. The porch is framed by green columns, and a gravel pathway leads towards the entrance.

4.96 out of 5 average rating, 313 reviews

South Bend Fully Restored Cottage Built in 1912

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, 326 reviews

Red Barn Lodge

Farm stay in Benton Harbor

An open living space features a combination of wood-paneled walls and ceiling with a polished hardwood floor. A spacious dining table and chairs are positioned beside a seating area, which includes a couch. A large bed is visible in the background, complemented by various window treatments.

4.99 out of 5 average rating, 106 reviews

Fogarty’s Flying Diamond Ranch

4.89 out of 5 average rating, 325 reviews

A sleek entertainment area is presented with a mounted flat-screen TV against a marbled feature wall. A wooden media console below holds decorative items and media storage. Greenery from a potted plant complements the modern aesthetic, contributing to a harmonious living space.

Home in St. Joseph

Cozy & Clean Entire Home in Saint Joseph

4.97 out of 5 average rating, 301 reviews

A cozy studio apartment features a comfortable bed with soft linens, a wooden coffee table, and a light-colored chest of drawers. Natural light filters in through a nearby window, illuminating the space. A green armchair is positioned in one corner, adding to the inviting ambiance.

Loft in Shipshewana

Hidden Country Hide-A-Way

4.86 out of 5 average rating, 108 reviews

A cozy sleeping area features a spacious bed with a soft, textured throw blanket draped over it. An antique world map hangs above the bed, complemented by warm pendant lights. A decorative pillow adds an inviting touch to the arrangement.

Cottage in Dowagiac

Vintage Romance Finds Cozy Charm at Depot 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

Family-friendly home rentals with a pool

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

4.94 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

Guest house in Cassopolis

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.

4.98 out of 5 average rating, 173 reviews

Couples cottage with hot tub!

4.96 out of 5 average rating, 225 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

4.85 out of 5 average rating, 196 reviews

A spacious green house features a traditional design with multiple windows on the upper level, bordered by well-maintained landscaping. A large driveway extends in front, accommodating parking for several vehicles, leading to a three-car garage with white doors.

Home in Union Pier

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

4.88 out of 5 average rating, 135 reviews

A stone pathway leads through lush greenery and colorful flowerbeds toward a light-filled, glass-fronted structure. Towering trees create a natural canopy, enhancing the serene atmosphere of the garden setting.

Home in Three Oaks

Harbor Country Charm w Heated Pool Open Til 10/12!

Guest house in Michigan City

The exterior of Lagunitas Coach House is shown, featuring a screened-in porch with two red chairs. Lush greenery and flowers surround the entrance, while a small table rests beside the chairs. A clear blue sky provides a bright backdrop.

4.86 out of 5 average rating, 163 reviews

Lagunitas Coach House in Beachwalk, Lake Michigan