Holiday rentals in Hillsdale

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!)

Bear Lake access/Getaway/family friendly-Bears Den

Bear Lake welcomes you. Relax with friends/family at this peaceful and sometimes spirited getaway steps away from ALL SPORT Bear Lake. Shared dock where you can swim, Kayak, fish, or merely float. A Public access launch is just yards away for personal watercraft. Evenings sprinkle the sky with plenty of stars to gaze at. Fishing, boating, kayaking, or just relaxing are all at your finger tips. Golfing, restaurants, shopping, and walking/ biking trails nearby. Pontoon/Kayak rentals available.

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.

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.

The Frogmore on Baw Beese Lake!

Welcome to Frogmore Cottage, located on the shoreline of Baw Beese Lake! Newly renovated and stocked with all you'll need, Frogmore is a clean, cozy, bright and airy, two bedroom, one bathroom, 550 square foot cottage. Frogmore is just two miles from downtown Hillsdale and three miles from Hillsdale College. Relax on the deck that overlooks the lake and enjoy the kayaks to explore the shoreline of the largest lake in Hillsdale County!

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.

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.

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.

Reedsong Cottage

Charming 2-bedroom lakeside cottage with a sleeper sofa, 1.5 baths, and stunning waterfront views. Relax on the dock, lounge outdoors, or explore the lake with included kayaks. Enjoy a full kitchen and spacious living room—perfect for up to 6 guests. Conveniently located just 2 miles from downtown Hillsdale and 3 miles from Hillsdale College.

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!

Luxurious Lochaven Condo

Nestled in the trees, come and stay in this newly built condo near everything Hillsdale has to offer. Minutes from downtown Hillsdale, Hillsdale College and Baw Beese Lake. Enjoy nature either on the screen porch or walking along the bike path.