Family-friendly holiday rentals in Hillsdale

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Hillsdale

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
Home in West Unity
4.95 out of 5 average rating, 142 reviews

Stray Chalet: 2-bedroom home on a quiet street

The Stray Chalet boasts a relaxing, clean and open space with no steps. It is a peaceful home in a quiet neighborhood . Relax in comfort with everything you need in a home away from home. We try our best to be allergen free! The home is located 1 block from the quaint downtown and just steps away from Wabash Park and the Wabash Cannonball trailhead. West Unity is right along the Ohio Turnpike between exit 13 and 25. There are many adventures awaiting locally and even more within an hour's drive.

Guest favourite
The open floor plan showcases a spacious dining area with a circular table surrounded by upholstered chairs. Natural light enters through multiple windows, illuminating the living space with a sectional sofa and a lamp. A staircase leads to the loft area, where four twin beds are visible.
Home in Homer
4.97 out of 5 average rating, 134 reviews

Benham Schoolhouse

Take a quiet vacation at this fully renovated historical schoolhouse built in the 1800's. It offers an open floorplan with a loft area where the four twin beds are located *can be made more private by closing the barn doors. There is two full bathrooms, a large kitchen area, living space, dining space, and an open area we can set up to be used for craft activities or other activities upon request. It also has a Halo air purification system, stopping virus particles to travel through the HVAC.

Top guest favourite
A hot tub is positioned under a wooden pergola, surrounded by lush greenery. The lake reflects a colorful sunset sky, and a well-maintained outdoor area features seating and a shed, creating a serene space for relaxation and enjoyment.
Home in Hillsdale
4.96 out of 5 average rating, 101 reviews

Sapphire Shores: Lakefront W/Hot Tub & Fireplace

Welcome to Sapphire Springs, your lakefront retreat on South Sand Lake, MI! Perfect for all seasons, this home offers endless fun indoors and out. Outside, enjoy a sandy beach, kayaks, paddleboards, a grill, fire pit, hot tub, and outdoor games. Indoors, unwind in the game room with a pool table, arcade games, and TV. Relax in the living room, spin some vinyl on the turntable, and cook up a feast in the fully equipped kitchen. The coffee station has an espresso machine, drip, and Chemex.

Top guest favourite
A welcoming entry features a set of stairs leading up to the cottage, flanked by white railings. A decorative American flag is displayed on the front porch, surrounded by landscaped areas with pebbled ground and greenery.
Cottage in Rome City
4.98 out of 5 average rating, 251 reviews

Lakeside Sylvan-Lake Rome City Cottage

Welcome to Sylvan Lake in Rome City, IN. Sylvan Lake is an all season ski lake wonderful for all boating, fishing, skiing, tubing, wave runners and even a swim from the dock. You have 60 feet of lake front with two docks to bring your lake toys or rent a pontoon for the day/weekend or week. Full size kitchen, laundry, two big smart tv's with cable and wifi. Small shed for storage, large deck, canoe for 3, fire pit & gas grill. Wedding, family, golfing or weekend away? Lakeside Sylvan!

Top guest favourite
The exterior of the Eppstein House is showcased amidst autumn foliage, featuring a low-slung, geometric design. Expansive glass doors reveal warm interior lighting, contrasting beautifully with the natural stone path and surrounding trees.
Home in Galesburg
4.96 out of 5 average rating, 466 reviews

Frank Lloyd Wright’s Eppstein House

Designed by Frank Lloyd Wright, the Eppstein House is a rare architectural gem nestled in the same region as Wright’s Meyer May House in Grand Rapids, the Gilmore Car Museum in Hickory Corners, and the charming beach town of South Haven. This is a unique opportunity to experience an extraordinary home—yours to enjoy for a few unforgettable days. Travel + Leisure named the Eppstein House as Michigan’s most unique Airbnb, effectively ranking it #1 in uniqueness for the state.

Guest favourite
A charming one-level cottage is positioned near Bear Lake, featuring a large concrete patio with patio furniture. A sandy area leads to the water, showcasing a private dock. The landscape includes green trees and grassy areas, contributing to a serene environment.
Home in Hillsdale
4.75 out of 5 average rating, 315 reviews

Bear Lake Cottage ... Pontoon Available for Rent

Quaint and cozy cottage on all-sports Bear Lake in Hillsdale, MI, offering a year-round peaceful and serene getaway. Bring your boats, campers and tents; there’s plenty of room for everyone. The outdoor fire pit is perfect for campfire bonding, and in fall and winter months, enjoy the fire overlooking the lake. Cottage is on a channel to Pike Lake - a calm, private lake. Take the kayaks and SUPs exploring, or enjoy ice skating or fishing when the lake’s frozen.

Top guest favourite
The farmhouse is nestled among greenery, featuring a wraparound porch and a private deck extending from the upper level. The structure showcases a gable roof and a chimney, surrounded by trees and lush grass.
Farm stay in Hillsdale
4.98 out of 5 average rating, 363 reviews

Bluebird Trails

This is a working farm with hands-on learning of organic gardening practices, market gardening, winter gardening, farmers market and CSA prep and sales, as well as sheep husbandry, including assisting with lamb births and herding. Other hands-on learning experiences include sourdough bread and jam making as well as canning. You will leave with increased knowledge of sustainable agriculture, self-sufficiency and a feeling of being at one with the earth.

Guest favourite
A serene lakeside scene is depicted at dusk, featuring silhouetted trees against a colorful sky. Four white Adirondack chairs are positioned neatly near the water's edge, inviting a moment of relaxation as vibrant hues reflect on the lake's surface.
Flat in Hillsdale
4.9 out of 5 average rating, 151 reviews

Come Stay At The Lake!

Enjoy your stay in this very private apartment on beautiful, Baw Beese Lake. If you are seeking a quiet stay where you can sit, relax and read a book at the water's edge, then look no further. There is parking for most any size vehicle from economy size to motor homes. This is a fully furnished apartment with kitchenette. This second story apartment is within 1 mile of downtown Hillsdale and within 2 miles of Hillsdale College.

Guest favourite
A hot tub is positioned on a wooden deck, overlooking a serene lake at dusk. String lights are draped above, casting a warm glow. Reflections of trees and a dock are visible on the calm water's surface, enhancing the tranquil atmosphere.
Home in Bronson
4.97 out of 5 average rating, 331 reviews

Lake house with great swimming and kayaks

Tranquil lake living! The Water’s Edge is a great way to enjoy the lake. It is right on the water with kayaks, stand up paddle boards, and a canoe to venture out with. The hot tub accommodates 6 people. The sunroom has beautiful views as well as a couple of beds that can be used if the weather is nice. There is nothing better than falling asleep to lake sounds and a pleasant breeze! Please no college partyers.

Top guest favourite
A raised treehouse structure is surrounded by tall pine trees in a woodland clearing. Two wooden Adirondack chairs are positioned on the ground, facing the entrance with green doors. A staircase leads up to the deck, providing access to the elevated space.
Treehouse in East Leroy
5 out of 5 average rating, 687 reviews

Outpost Treehouse

The lookout inspired Outpost Treehouse (not actually attached to a tree) sits in a white pine forest in the middle of a 50 acre active farm. The 15 hand crafted windows allow for great views watching out for Michigan wildlife--White tail deer, turkeys, owls, coyote have all been spotted from the elevated wrap around deck. The biggest regret that guests have noted is “we wish we would have stayed longer”!

Guest favourite
A modern, single-story home is depicted, featuring a combination of red and gray siding. The structure includes large windows and a welcoming entrance with a sign that reads 'Proctor House.' A landscaped area with stone retaining walls and a grassy lawn is visible in the foreground.
Home in Hillsdale
4.89 out of 5 average rating, 285 reviews

Comfy home in recreational town

We renovated the house with a modern kitchen, laundry room, new bathroom with spacious shower, new bedrooms with plenty of closet space, secure parking and new sidewalks. Close to historic weekly country market, Hillsdale College, bike trail, lakes in historic town. The North Country Trail and the Baw Beese Trail are closeby, as is Baw Beese Lake, Lost Nation State Game Area and the St. Joe River.

Top guest favourite
A charming white structure with a light grey roof is set against a backdrop of lush green grass and large trees. An American flag is displayed at the entrance, and a decorative stone feature is visible in the background, contributing to the property’s rustic character.
Home in Parma
4.95 out of 5 average rating, 436 reviews

Stay In An Old Train Depot - Gidley Station!

Be adventurous and stay in rustic old Gidley Station. It was moved to "Trail Acres" in the 1920's and was converted to a house. It has a unique but spacious floor plan, and is on a property that we have been working hard to restore for the last few years. PLEASE READ FULL DESCRIPTION BEFORE BOOKING!

Popular amenities for Hillsdale family-friendly rentals

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Quick stats about holiday rentals that are family-friendly in Hillsdale

  • Total holiday rentals

    Explore 30 holiday rentals in Hillsdale

  • Nightly prices starting at

    Hillsdale holiday rentals start at ÂŁ52 per night before taxes and fees

  • Verified guest reviews

    Over 1,270 verified reviews to help you choose

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Hillsdale holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hillsdale rentals

  • 4.9 Average rating

    Hillsdale stays are highly rated by guests – averaging 4.9 out of 5!

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