Holiday houses in Hillsdale

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Top-rated holiday rentals in Hillsdale

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Guest favourite
The open floor plan showcases a spacious dining area with a circular table surrounded by upholstered chairs. Natural light enters through multiple windows, illuminating the living space with a sectional sofa and a lamp. A staircase leads to the loft area, where four twin beds are visible.
Home in Homer
4.97 out of 5 average rating, 134 reviews

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.

Guest favourite
Home in Osseo
4.92 out of 5 average rating, 25 reviews

Cozy Lakefront Home minutes from Hillsdale College

Welcome to our lakefront home on Bird Lake—where relaxation, comfort, and fun come together. Nestled directly on the shoreline, this beautifully updated retreat offers breathtaking views, direct water access, and remodeled living spaces, making it an ideal escape for families, couples, or friends. Begin each day with stunning sunrises and unforgettable views from your private deck. Inside, the remodeled main living area features an open floor plan designed to keep everyone connected.

Guest favourite
A charming two-story home is framed by leafy trees and greenery. The exterior features light-colored siding, dark shutters, and a front porch with steps leading to the entrance. A well-maintained yard displays shrubbery and seasonal flowers, enhancing the inviting appearance of the property.
Home in Hillsdale
4.92 out of 5 average rating, 51 reviews

The Homestead at Hillsdale (.4 miles from campus)

Welcome to our peaceful, clean, and beautiful home in the heart of Historic Hillsdale. This recently renovated home is conveniently located 3.5 blocks from Hillsdale College and 3 blocks from the historic downtown. We aim to provide the best accommodations in town. Our guests can expect premium, locally-roasted coffee, high-quality cotton linens, a brand-new fire pit in a cozy backyard, and much more. Come see why The Homestead is the go-to place to stay in Hillsdale.

Top Guest favourite
A rustic living area features a leather sofa adorned with black and white checkered pillows. Exposed wooden beams and walls create a warm atmosphere, while a wooden staircase with logs leads to the upper level. A soft carpet covers the floor.
Home in Jonesville
5 out of 5 average rating, 32 reviews

Newly Renovated / Bullhead Lake

Enjoy a family-friendly getaway at this newly remodeled lakeside retreat! With rustic charm, modern updates, and new AC, furnace, and appliances, it’s the perfect mix of comfort and style. Located on Bullhead Lake, just 4 miles from Hillsdale College and a half-mile from Walmart, you’ll love the convenience. Relax on the deck and take in stunning sunsets over the lake, or explore the nearby area for plenty of activities. Hot tub available with an additional cost!

Top Guest favourite
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
4.98 out of 5 average rating, 42 reviews

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!

Guest favourite
A waterfront cabin is depicted with a large glass front, allowing ample natural light inside. Lush green grass surrounds the house, complemented by tall trees. A pathway leads to a spacious deck area with outdoor seating and a grill, enhancing outdoor relaxation opportunities.
Home in Coldwater
4.84 out of 5 average rating, 112 reviews

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.

Guest favourite
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.
Home in Hillsdale
4.89 out of 5 average rating, 285 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.

Top Guest favourite
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
4.98 out of 5 average rating, 108 reviews

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.

Top Guest favourite
The lakeside view captures a tranquil sunset over the water, framed by trees. A three-season room with warm lighting is visible, inviting relaxation. The reflection on the lake adds a serene quality to the atmosphere, enhancing the peaceful setting.
Home in Hillsdale
5 out of 5 average rating, 38 reviews

Firefly Cottage Lake front home on Baw Beese Lake

Lakeside Family Fun! Lake front house, on the quiet end of Baw Beese Lake. 3 bedroom, 1.5 baths. 45 feet of sea walled lake front, with a 28-foot dock. Yard games. Lake side firepit. 3 season room. Kayaks, canoe, SUPs, and a few floats for your enjoyment. A well-stocked kitchen, and a full-size gas grill for your use. Central air for those hot summer nights.

Top Guest favourite
Home in Hillsdale
4.98 out of 5 average rating, 65 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.

Guest favourite
Home in Hillsdale
4.89 out of 5 average rating, 19 reviews

A Home in Hillsdale

Relax with the whole family at this peaceful place to stay. Minutes walk to downtown activities, parks, and shopping. 20 minute walk to Hillsdale College. 15 minute walk/ 3 minute drive to Hillsdale Hospital. 10 minute drive to Sandy Beach at Baw Beese Lake. 39 minutes to Michigan International Speedway. Less than an hour to Firekeepers Casino.

Guest favourite
A two-story home is set amidst a grassy area, bordered by trees and shrubs. A gravel driveway leads to a two-car garage, providing convenient access. Sunlight filters through the trees, casting soft shadows on the ground.
Home in Osseo
5 out of 5 average rating, 28 reviews

Two story 3 bedroom home; master suite,deck,yard

Two story 3 bedroom 2 bath home includes king master suite with jacuzzi tub,2 upstairs bedrooms, 1 full 1 Queen,fully equipped eat in kitchen, front load washer and dryer,central heat and air,huge deck and back yard. Located on M-99 Less than 5 miles from downtown,Hillsdale college, halter shooting center, Baw beese lake and parks.

Popular amenities for Hillsdale holiday rentals

When is the best time to visit Hillsdale?

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Avg. price$288 AUD$287 AUD$291 AUD$251 AUD$314 AUD$281 AUD$257 AUD$244 AUD$237 AUD$241 AUD$261 AUD$238 AUD
Avg. temp-2°C-1°C4°C11°C17°C22°C24°C23°C19°C13°C6°C0°C

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Hillsdale?

    Yes! Work meets play with ease at over 30 vacation rentals in Hillsdale featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Hillsdale?

    Hillsdale has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Hillsdale?

    Experience the best of Hillsdale with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Hillsdale have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Hillsdale. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Hillsdale have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Hillsdale. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Hillsdale?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Hillsdale

  • Total holiday rentals

    Explore 40 holiday rentals in Hillsdale

  • Nightly prices starting at

    Hillsdale holiday rentals start at $72 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,900 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Hillsdale holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Hillsdale rentals

  • 4.9 Average rating

    Hillsdale stays are highly rated by guests—averaging 4.9 out of 5!

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