Family-friendly vacation rentals in Chikaming Township

4.99 out of 5 average rating, 523 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.

4.85 out of 5 average rating, 109 reviews

A large screened front porch is furnished with several wooden rocking chairs and a wicker seating area. Natural light filters through the screens, showcasing the surrounding greenery. A small table sits centrally, creating an inviting space for relaxation and conversation.

Cabin in Three Oaks

Cabin with POOL in family resort!

Nestled within a gated 67-acre resort and just minutes from the shores of Lake Michigan, this charming cabin offers a peaceful retreat ideal for couples, families, or solo travelers, blending rustic décor with modern comforts. Guests can spend their days exploring nearby nature trails, lounging by the pool, paddling across the lake, or unwinding on the porch. The perfect vacation for exploring nearby orchards and countryside, catching live music or theater, or just slowing down and recharging!

4.99 out of 5 average rating, 119 reviews

A spacious living area features large French doors that open to a deck. A neutral-toned sofa is adorned with decorative pillows, while a wooden coffee table sits in front. An inviting armchair and framed artwork complement the warm, natural lighting filtering in.

Cottage in Sawyer

The Cottage of Harbor Country - Close to it all!

Welcome to your very own Cottage in Harbor Country! The perfect weekend getaway from Chicago, our cottage is close to Warren Dunes and just a 15-20 minute walk to Lake Michigan. Renovated and beautifully appointed, it blends vintage charm with modern updates! Enjoy morning coffee on the new deck or screened-in porch, take a dip in the new hot tub, or cozy up next to the wood-burning fireplace. Enjoy the perfect place to relax, hike, go antiquing, wine-tasting, and make memories with loved ones!

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, 230 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.

4.99 out of 5 average rating, 156 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

Please note: Summer stays are 7 night minimums from Friday to Friday. Welcome to our cozy 'Tree House,' nestled among the trees in Lakeside, Michigan! Our renovated cottage is 90 minutes from Chicago in the heart of Harbor Country. Our bright, open home features high end finishes and luxury mattresses. Nature-inspired hues invite you in, making relaxation a top priority! Generous outdoor spaces include a deck with dining area, rocking chairs, and two fire pits for s'mores under the stars.

4.91 out of 5 average rating, 138 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

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.

4.97 out of 5 average rating, 177 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!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

4.97 out of 5 average rating, 221 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.

Bungalow in Sawyer

Family Getaway with Year Round Hot Tub!

Welcome to Harbert in Harbor Country! The House on the Prairie is tucked away in a quiet location in Harbert, yet minutes from the beaches, dunes, breweries, wineries and all the Harbor Country attractions. The house features tons of amenities and is packed full of games, toys, books and activities for all ages. Enjoy the back yard amenities with a hot tub, firepit, hammock & deck! Even includes a tree house, sandpit and trampoline for the kids! Hot Tub open all year round!

Superhost

Cottage in Three Oaks

4.82 out of 5 average rating, 202 reviews

Hot Tub • Sauna • Billiards | Stay & Play!

Wanna Play?? You name the game & we probably have it! Outdoor fun includes Pickleball & Volleyball nets, Putting Green, corn hole and even cruiser bikes. Indoor fun incl. BILLIARDS & table tennis, complete poker set & board games galore! If you prefer to take it easy you can relax in our YEAR-ROUND hot tub, cozy up by the gas fireplace or the outdoor fire pit, unwind in the indoor SAUNA or stroll to nearby Harbert Beach. Whatever your choice, THIS is the place to STAY & PLAY!

4.89 out of 5 average rating, 121 reviews

Two white Adirondack chairs are positioned adjacent to a circular fire pit. The ground is covered with colorful fallen leaves, and trees with yellow foliage provide a natural backdrop. The scene reflects a serene outdoor space ideal for relaxation.

Apartment in Sawyer

Morton's Retreat Cozy 1 Bedroom Apartment

Cozy comfort close to Michigan's most popular state park, breweries, wineries, antique malls and farm-to-table restaurants. Morton's Retreat has plenty of room to relax. Charcoal grill and fire pit (shared with Morton’s other retreat) for use in a spacious yard. Private entrance with keyless entry makes check-in a breeze. One other Airbnb located next door in same building. Two complimentary seltzer waters and snacks are provided to help kick off your stay.

4.98 out of 5 average rating, 123 reviews

A cottage exterior is showcased with blue siding and a welcoming porch. Lush greenery and colorful flowers surround the home, adding to its appeal. Large windows offer ample natural light, while trees enhance the privacy of the property.

Cottage in Lakeside

Pebble Path Cottage - Less than a block to beach!

Charming vacation home in Harbor Country, only 75 miles from Chicago. The cottage is less than a block from a wide, sandy private association beach where you can walk for miles, swim, or relax on the shore. It is perfectly situated to visit local farm stands, wineries, breweries, restaurants, & state parks. No smoking and no pets, please. Checkout our sister cottage next door - Morning Dove Cottage

A light-filled living area features a cozy sofa with decorative pillows, two comfortable armchairs, and a stone fireplace. A flat-screen television is mounted on the wall, and a small table holds decorative plants. Natural light enters through multiple windows.

4.98 out of 5 average rating, 117 reviews

Harbert Woods - 5 min walk to beach!

2 bed, 1 bath, 3 minute walk to private beach and Lake Michigan, this charming getaway is located in the gorgeous, secluded, Harbert Woods neighborhood. Home includes well stocked kitchen, new appliances, new beds & furniture, gas grill, fire table, wood fireplace, 20 x 30 foot deck. Streaming TV, WiFi, W&D, central AC/heat, turntable with records, bluetooth music & Alexa. 2 night minimum.

Popular amenities for Chikaming Township family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A cedar barrel sauna is set against a lush green backdrop. The entrance features a clear glass door and is adorned with cozy red blankets and a fabric tote bag hanging nearby. The wooden deck provides a warm contrast to the vibrant outdoor foliage.

4.99 out of 5 average rating, 136 reviews

Pet friendly stylish retreat with sauna, hot tub

4.95 out of 5 average rating, 198 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, 276 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

Lux, Creekside, Escape to Tranquility, Private,

4.96 out of 5 average rating, 230 reviews

The open living area features large floor-to-ceiling windows framing views of the surrounding woods. A sleek two-tone sofa and modern armchairs are arranged near a minimal table. Warm wooden flooring complements the contemporary design, and a staircase leads to the upper level.

Home in Beverly Shores

Secluded Modern Retreat Near Beach - "Sandlot"

4.98 out of 5 average rating, 115 reviews

A spacious common area is filled with soft natural light from an array of tall windows. Comfortable seating is arranged around a central table, with a mix of sofas and accent chairs. A textured area rug anchors the space, complemented by decorative lighting fixtures.

Home in Harbert

Harbert Home & Guest House

4.98 out of 5 average rating, 230 reviews

A hot tub sits on a deck overlooking Stone Lake, reflecting the vibrant colors of the sunset in its still water. The sky is filled with hues of orange, pink, and purple, providing a serene backdrop to the tranquil lake and surrounding trees.

Home in La Porte

Aunt Betty's Lakeside Abode, Hot Tub Steam Shower

4.83 out of 5 average rating, 133 reviews

The kitchen features white cabinets and modern appliances, including a microwave and stove. Sturdy wooden chairs sit outside the window, providing a comfortable spot for relaxation. The three-season porch showcases a cozy couch, a vibrant accent piece, and a convenient hot tub in the corner.

Home in Sawyer

Charming Cottage w/ Hot Tub

4.98 out of 5 average rating, 146 reviews

The exterior of a farmhouse is displayed, featuring a two-story structure with a red roof and white siding. A spacious deck with seating overlooks the manicured lawn, which is surrounded by trees. Bright red chairs are arranged on the ground, inviting relaxation.

Farm stay in Galien

FARM 10 acres, pond, Hot tub, king bed 30 min ND

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 106 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

4.94 out of 5 average rating, 134 reviews

The exterior of a Craftsman-style farmhouse is shown, featuring a covered front porch with seating and a well-maintained pathway. Lush landscaping includes flowering plants and trees, complementing the light-colored siding and dark roof under a clear blue sky.

Farm stay in Bridgman

Luxury Craftsman Farmhouse Near Beaches & Wineries

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, 155 reviews

Dog Friendly Downtown Three Oaks Cottage! Fenced!

4.88 out of 5 average rating, 208 reviews

The exterior of the barn showcases a vibrant red facade adorned with greenery. Large overhanging vines and trees frame the entrance, creating a welcoming atmosphere. A paved area leads to the barn, with side windows visible on the left. This setting hints at a rustic charm.

Cottage in Sawyer

Northwind Llama retreat 'Loft Cottage'

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

4.91 out of 5 average rating, 127 reviews

A charming cottage is depicted with a large deck featuring outdoor seating and a blue umbrella. The surrounding area showcases a well-maintained lawn and lush trees, with a barbecue grill visible in the background.

Home in Lakeside

Secluded Garden New Buffalo/Lakeside MI

4.97 out of 5 average rating, 253 reviews

Casa Gitana - Boutique Style Stay in Three Oaks

4.9 out of 5 average rating, 258 reviews

An open living space showcases a blend of modern and rustic design elements. A spacious kitchen features stainless steel appliances, with bar stools positioned at the counter. Natural light filters in through large windows, illuminating the polished hardwood floors.

Home in Union Pier

CASA TICA Serenity Amongst Nature Dog Friendly

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 108 reviews

The multi-story townhome features a light exterior with spacious balconies on each level. Large windows illuminate the structure, enhancing its architectural details. Staircases lead up to the front entrance, inviting guests into the living space.

Townhouse in New Buffalo

Dunescape Beach Retreat, Downtown New Buffalo

A private pool area features a sparkling blue pool with a shallow entry and a floating pool lounge. Six lounge chairs are positioned under large umbrellas on a sun-soaked patio, offering shaded spaces for relaxation. The surrounding green trees provide a serene backdrop.

5 out of 5 average rating, 26 reviews

Updated Lakeside | Pool (Open!) + Hot Tub + Porch

4.94 out of 5 average rating, 174 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

A large heated saltwater pool is set in a manicured grassy area, surrounded by trees. The spacious house features multiple windows, reflecting natural light. Comfortable seating options are visible on a deck beside the pool, inviting relaxation in a private outdoor setting.

5 out of 5 average rating, 35 reviews

Private! Cherry Beach Pool House

4.97 out of 5 average rating, 128 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

4.92 out of 5 average rating, 333 reviews

A backyard oasis is showcased at dusk, with a heated pool reflecting warm lights strung overhead. Colorful pool floats gently rest on the water's surface, while a fire pit table is positioned nearby surrounded by Adirondack chairs, enhancing the inviting atmosphere.

Home in South Bend

Pool | Hot Tub | Backyard Oasis | Game Room | Fun

5 out of 5 average rating, 205 reviews

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.

Home in New Buffalo

Designer Cottage - walking distance to downtown

An outdoor view of the property showcases a wooden deck surrounding a heated plunge pool. The brown exterior of the house is framed by lush greenery, with seating areas and a gas BBQ grill visible. A secondary building is partially seen to the right.