Family-friendly vacation rentals in Hillsdale

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.

Secluded Lakehouse w/ Hot Tub, Sauna & game room

Get away to the quiet of a lake in a secluded paradise! Enjoy an amazing panoramic view of Little Pleasant Lake while soaking in a hot tub and chilling out in a steaming barrel sauna in the woods. Kayak and fish for hours. Hike the area trails in fall leaves or quiet snow. Light a bonfire after games of corn-hole and table tennis. Unwind on the upstairs balcony with a glass of wine and lake sounds. This is the escape you’ve been needing. Perfect for romantic couples and family vacations.

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.

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.

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.

Stay in a YURT on An Equine Rescue Ranch

The yurt is located on a 30 Acre Equine Rescue ranch. It is a 4 season 20ft yurt in the middle of the ranch with a beautiful view of Mustangs (American Legends). All proceeds from rental will go back to the rescue. There is electric, an outhouse a short walk away, a cold water spigot close by. Minutes away from Pleasant Lake for swimming, a local winery & 38 minutes from Ann Arbor. We offer tours and chances to interact with equines, including American Mustangs!

Quiet Home Away from Home!

Forget your worries in this spacious and serene space. Quiet, safe, and outside city limits. Private entrance and dedicated heating and cooling. Electric fireplace for cold nights. Queen size bed and full size pull out couch. Smart TV in Living Room and Bedroom. Work desk, PC, and printer for your use. Fully stocked kitchen with all appliances and utensils. Walk in shower, stackable washer and dryer, and walk-in closet. Entire property is handicap accessible.

The Post Office Near Clear Lake

Sip on a cup of coffee, and relax in your peaceful private getaway. This one-of-a-kind former 1902 post office that was converted into a stay. Surrounded by rolling farms fields and located at the Mill District. Guests are in awe when they arrive and see how beautiful the grounds are. Feel free to explore the grounds and bring your photographer (No sitting fee). Great peaceful location with a short drive to clear lake.

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.

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!