
Family-friendly vacation rentals in Hillsdale
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Hillsdale

Total vacation rentals
Explore 30 vacation rentals in Hillsdale

Nightly prices starting at
Hillsdale vacation rentals start at G$14,633 GYD per night before taxes and fees

Verified guest reviews
Over 1,380 verified reviews to help you choose

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Hillsdale vacation rentals include wi-fi 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!
Top-rated family-friendly rentals in Hillsdale
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Private Lakefront, Hot Tub, Kayaks
*Lakeside Luxury Awaits: Your Tranquil Escape* Immerse yourself in the serenity of lakeside living at this stunning retreat, perfectly positioned just 10 minutes from the natural beauty of Pokehagen State Park. This 3-bedroom haven offers an unparalleled escape for families and friends seeking relaxation and adventure. Wake up to breathtaking lake views from almost every room. The sunroom beckons with its cozy ambiance, ideal for enjoying your morning coffee or losing yourself in a good book.
Indoor spacesFamilyGetting around

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.
KitchenIndoor spacesAccess

Hillsdale Cottage | Whole House
This recently renovated home offers the perfect blend of historic charm and modern comfort, with original architecture, cozy interiors, and a welcoming porch. Ideal for both short- and long-term stays, with a fully stocked kitchen and four comfortable beds. Walking distance from Hillsdale College and directly across from Handmade sandwich shop. Exclusively 100% cotton sheets and non-toxic cleaning products are used! (Be sure to specify the accurate # guests when booking a stay at the Cottage!)
Indoor spacesKitchenLocation

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.
FamilyKitchenWalkability

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.
KitchenIndoor spacesView

Stunnnig House on Marble lake with private beach🏖
Our cozy lake front home offers both summer and winter fun with amazing views of beautiful Lake Marble. The direct water access allows family and friends the ability to swim, fish, and boat with ease and convenience. Our 4 bedroom home sleeps up to 10 comfortably with 3 full bathrooms. You will find our home fully furnished with everything you would need. 17 miles of lakes connected by channels. Minutes away from Allen Michigan, the Antique Capital of the World.
FamilyIndoor spacesParking

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.
FamilyIndoor spacesBathroom

Coldwater Lake Waterfront Cabin - Boat for Rent
Relax with the whole family at this peaceful waterfront lakehouse, with walk-in, sandy beach lake access. Boat available to rent, and space available for your boats. Spacious yard with plenty of parking. Coldwater Lake is over 1,600 acres of all-sports fun on desirable South Chain of Lakes in Coldwater, MI. The chain is 17 miles, traversable via pontoon or speedboat! The Cabin includes 3 bedrooms and 2.5 baths.
FamilyKitchenLayout

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.
KitchenIndoor spacesLong stay

The Rupp House
Make your Hillsdale County home base in one of the earliest houses in Jonesville, conveniently located 10 minutes from Hillsdale College. The house is a solid preserved house which invites you to kick off your shoes and relax. It has a full kitchen, a large dining table and beds for 6 persons. There is one bathroom which has a shower and plenty of hot water. Full kitchen. Washer and dryer.
Indoor spacesKitchenSleep quality

Hillsdale’s Hidden Condo Hideaway
This is a newly built, luxurious condo with 3 bedrooms and 2 bathrooms featuring cathedral ceilings, a large kitchen island, and gorgeous master bathroom. It is located in a quiet, rural neighborhood. If you enjoy the outdoors, there is a paved walking path to Baw Beese Lake. This home is 2 miles from Hillsdale College and just minutes from downtown Hillsdale.
Indoor spacesFamilyBathroom

Cozy Cottage Near Campus
What a perfect location! This cabin is a short walk down the sidewalk to Hillsdale College campus and steps away from Hayden Park with its new track stadium, sand volleyball, and running trails. You'll enjoy relaxing in this cozy cabin or watching wildlife in the spacious backyard. You're also just minutes from downtown Hillsdale, shops, and restaurants.
Indoor spacesKitchenWalkability
Popular amenities for Hillsdale family-friendly rentals
Family-friendly home rentals with a hot tub

Lakefront Getaway: Private dock, HOT TUB & kayaks
Indoor spacesKitchenCheck-in

Secluded Lakehouse w/ Hot Tub, Sauna & game room
FamilyIndoor spacesAccess

Peaceful 3 Bedroom Cottage with Lake Access
Indoor spacesFamilyCheckout

Lakefront Wonderland | Dock, Game Room & Hot tub
FamilyKitchenCheck-in

Couples spa retreat suite getaway. Hot tub
FamilyKitchenCleanliness

Quiet Getaway w/ Hot Tub + Fire Pit | Lake Access
KitchenFamilyValue

Farm Cottage with Hot Tub, Sauna, Fire Pit, Trails
KitchenIndoor spacesHospitality

Tree House Studio
FamilyIndoor spacesLayout
Family- and pet-friendly home rentals

Baughman's Cove
Indoor spacesFamilyDecor

Little Cabin in the Woods-Quiet
Indoor spacesFamilyPets

20a Cabinn - Private cabin on 10 woodland acres
FamilyIndoor spacesOutdoor spaces

Newly Designed Beach Front Get Away
KitchenIndoor spacesBathroom

Cozy Cottage Getaway on Evan’s Lake
FamilyIndoor spacesOutdoor spaces

Lakefront Nostalgic Cottage
KitchenIndoor spacesCheckout

Beautiful Studio
KitchenIndoor spacesGetting around

Cozy Tiny House on Centennial Farm
FamilyIndoor spacesWifi
Family-friendly home rentals with a pool

Turtle Cove Lakefront, pool, hot tub, Sauna!
Indoor spacesFamilyNearby

LIL Carrot- hot tub, pets welcome
FamilyKitchenDecor

Heated Pool /Hot Tub Villa
FamilyIndoor spacesTV

Great Wood Lodge
KitchenFamilyPool

Oasis Retreat with Pool and Sauna!
FamilyIndoor spacesBathroom

Bent Oak Estate
Indoor spacesKitchenHospitality

Annie's Place behind the winery
FamilyKitchenPets

Luxury lake-house and heated salt pool
Indoor spacesFamilyPool
When is the best time to visit Hillsdale?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$43,898 GYD | G$45,779 GYD | G$45,988 GYD | G$44,525 GYD | G$49,960 GYD | G$47,242 GYD | G$43,062 GYD | G$45,988 GYD | G$45,988 GYD | G$45,988 GYD | G$45,152 GYD | G$43,271 GYD |
| 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 |
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