
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.

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.

The Feral Skoolie
Nestled on 4 acres and located in the heart of Waterloo recreation area, this 280sq ft skoolie boasts comfort and eclectic energy! Sure to please the outdoor enthusiast, the property is surrounded by public land with the Pinckney Waterloo Trail crossing at the end of our driveway, and several nearby lakes. Located 30 minutes to Ann Arbor, 15 minutes to downtown Chelsea which offers plenty of great eats and drinks, 20 minutes to downtown Jackson, 10 minutes to Sandhill crane winery.

Cozy Lakefront Cottage on Huyck Lake
Relax with the whole family at this peaceful, cozy place! 3 bedrooms 1 bath. Living room has a comfortable couch that pulls out into a bed along with additional seating. Full bath, kitchen, and laundry room are fully stocked for your comfort and enjoyment. Huyck Lake is a quiet, no wake lake. This house is perfect for a small to medium sized family or a romantic getaway. Master bedroom and guest bedroom have mounted TV’s. Family friendly. No to the following: pets, smoking, parties.

Little Cabin in the Woods-Quiet
Need a quiet, secluded getaway? Our off-grid cabin is on approximately 10 acres of private woods. As you turn off the main road into our cabin's driveway, you will begin to understand why this is our hidden gem. Enjoy the coziness of a wood-stove in the winter or a crackling fire in seclusion in the summer- this little getaway cabin is sure to create fond memories. Maybe you will hear the horned owl at night or see an eagle while you kayak. Your adventure or a peaceful vacation awaits.

20a Cabinn - Private cabin on 10 woodland acres
Relax with the whole family at this peaceful, rustic and freshly remodeled cabin. Located right off the Archbold turnpike exit just miles away from Sauders village. Enjoy staying inside by the cozy fireplace, 10 acres of wooded property along the tiffin river, direct access to fish the river, and enjoy miles of Scenic views with direct access to the Cannon-Wabash Bike and Walking trail! Room for plenty of guests with 3 bedrooms one king, two queens and a pull out couch.

Stunning Studio
Lovely one bedroom studio just a four minute walk from Marshall’s beautiful historic downtown! Shop, eat, and explore this bustling community with a small-town feel! Enjoy our full itinerary of local events, or explore other wonderful local communities. Marshall’s proximity to intersecting state highways I-94, and I-69 offers a perfect spot to access all the bounties the State of Michigan has to offer. Come explore the Great Lake State in comfort and style!

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.

Relaxing Cottage Near Clear Lake
Relax and unwind at our peaceful cottage at The Mill District. You will love the views out of the floor to ceiling windows. Everything inside and outside the cottage was recently remodeled including a brand new bathroom. You and your guests will love the well manicured property. Feel free to explore the grounds and bring your photographer (No sitting fee for guests). Peaceful location located next to clear lake.

Water’s Edge-Lakefront-Hot Tub-Kayaks-Pet Friendly
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.

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.

The Garden House
Relax with the whole family in this charming old home, with swings on the front porch and an overgrown English cottage garden in back. Less than ten minutes from Hillsdale College with a fully equipped kitchen, this makes a great home base for college families. When we travel, we enjoy places with character, and we have maintained the character of this old fashioned family home.

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
Family-friendly home rentals with a hot tub

Cottage on Wilder Creek with Hot Tub

The Enchanted Schoolhouse

Secluded Lakehouse w/ Hot Tub, Sauna & game room

Sweezey Oaks

No Wake Lake Lodge

Tree House Studio

Modern Flat on Organic Farm

|HOT TUB|Private Lake Access|Steps to the Lake|
Family- and pet-friendly home rentals

Crystal Blue Oasis - Family- and Pet-Friendly

Stunnnig House on Marble lake with private beach🏖

**Lakefront** Updated Open Concept Gem

Cozy Tiny House on Centennial Farm

Chelsea Lake House, Game Room, & Pontoon-rental

Cattle Ranch, Country Charm & Easy Urban Access

Peaceful, Rustic Tipi on Beautiful Union Lake, MI

Newly Designed Beach Front Get Away
Family-friendly home rentals with a pool

Luxury lake-house and heated salt pool

4 Person Rustic Cabin

Poolside suite

HotTub/BBQ/FirePit • GameRoom • MovieTheater&more!

Annie's Place behind the winery

Heated Pool /Hot Tub Villa

Cozy one bedroom apartment

Bent Oak Estate
When is the best time to visit Hillsdale?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $263 SGD | $291 SGD | $281 SGD | $271 SGD | $296 SGD | $278 SGD | $260 SGD | $278 SGD | $278 SGD | $278 SGD | $273 SGD | $262 SGD |
| Avg. temp | -2°C | -1°C | 4°C | 11°C | 17°C | 22°C | 24°C | 23°C | 19°C | 13°C | 6°C | 0°C |
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 $88Â SGD per night before taxes and fees

Verified guest reviews
Over 1,230 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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