Holiday rentals in Hillsdale County

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.

4.95 out of 5 average rating, 87 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.

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.

4.75 out of 5 average rating, 310 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.

5 out of 5 average rating, 5 reviews

Cabin in Osseo

Cowboy's Wolf Den

This unique little hand crafted canin is close to everything, making it easy to plan your visit. This is a rustic primitive cabin bring your own beds or there's two cots available This cabin Sits in our Rustic hand crafted Cowboy Town 🐎 complete with horses, pond for fishing or paddling around, river for exploring, lots of hiking and horse trails, close to bathroom and outdoor shower along with the kitchen area lots of wildlife and wilderness to enjoy

4.97 out of 5 average rating, 39 reviews

The exterior of Frogmore Cottage features a welcoming deck with handmade Adirondack chairs overlooking the surrounding greenery. Bright kayaks are stacked beside the cottage, ready for use. The driveway runs alongside, providing parking access. A neatly landscaped area enhances the cottage's inviting exterior.

Cottage in Hillsdale

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!

4.9 out of 5 average rating, 151 reviews

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

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 house in Jonesville

A spacious living area features hardwood floors and warm orange walls. A comfortable sofa sits on a patterned area rug, with a small table and two stools nearby. Bright recessed lighting highlights the room, and two skylights allow natural light to filter in.

5 out of 5 average rating, 78 reviews

Loft Apartment

Welcome to our charming loft apartment, located off of US-12 in Jonesville, just minutes from Hillsdale College. This apartment is perfect for a couple, or young family looking for a comfortable place to stay while they are in the area. The apartment features a living area, an efficiency kitchen, and a full bathroom. We hope you enjoy your stay at our loft apartment, and we look forward to welcoming you to our home!

A historic home is framed by vibrant autumn trees, showcasing hues of red, orange, and yellow. A wide front porch invites relaxation, and an American flag adds a touch of character. The surrounding walkways are lined with fallen leaves, creating a welcoming outdoor space.

5 out of 5 average rating, 17 reviews

Hillsdale Haven

Welcome to Hillsdale Haven, a beautiful historic home located along one of the nicest streets of downtown Hillsdale, Michigan. This cozy, three bedroom, two bathroom home is 2 blocks from Hillsdale Hospital, 4 blocks from the commercial district, and a short drive (1 mile) from Hillsdale College. Loaded with charm, the Hillsdale Haven has everything you need for a restful stay in Hillsdale, Michigan.

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.

4.89 out of 5 average rating, 283 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.

4.98 out of 5 average rating, 105 reviews

The exterior of a charming white house is framed by vibrant autumn foliage. A mix of orange and red leaves from nearby trees can be seen, along with a green lawn and a white picket fence in the background. An American flag is visible, adding to the inviting atmosphere.

Home in Jonesville

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.

4.98 out of 5 average rating, 61 reviews

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.

A charming cabin is positioned amidst lush greenery, featuring a prominent stone chimney. A paved walkway leads to the inviting entrance, framed by well-maintained lawns and tall trees under a clear blue sky.

4.9 out of 5 average rating, 21 reviews

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.