House vacation rentals in Hillsdale County

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Top-rated house rentals in Hillsdale County

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Top guest favourite
A spacious living area features a comfortable gray sofa facing a TV mounted on the wall. A dining table with white chairs is visible in the background, alongside a set of round tables with upholstered chairs. Natural light filters through vertical blinds on the windows.
Home in Osseo
5 out of 5 average rating, 20 reviews

Cozy Lakefront Home minutes from Hillsdale College

Wake up to breathtaking water views and step right outside to enjoy direct access to the lake for swimming, boating, or casting a line. Whether you’re here for adventure or relaxation, this home offers the best of both worlds. Inside, you’ll find a brand-new recreational room with a cozy bar, games, a large TV, and plenty of comfortable seating—ideal for family fun, rainy-day entertainment, or winding down together in the evenings. Come make some memories at the lake!

Top guest favourite
A single-story home is set on a well-maintained lawn, surrounded by lush greenery. A welcoming pathway leads to the entrance, with rocking chairs placed on the covered porch. Soft light filters through the trees, providing a serene atmosphere.
Home in Hillsdale
5 out of 5 average rating, 37 reviews

The Arbor View Hillsdale Stunning, 1 mi to College

This updated, well appointed home is the perfect place to stay for anyone visiting Hillsdale College. The home sits on a quiet, tree lined cul-de-sac, located 1 mile from the college and minutes away from quaint downtown Hillsdale. Guests will enjoy exceptionally clean, beautifully decorated guest rooms and living spaces, overlooking a serene wooded yard. The rental space is the main floor of the house (2,400 sq. ft). Host occupies private lower level of the home.

Superhost
A well-maintained home is featured, showcasing a welcoming front porch with white railings and an American flag. Lush greenery surrounds the entrance, and a pathway leads to a stone-lined garden. The exterior reflects a traditional aesthetic against a clear blue sky.
Home in Hillsdale
4.74 out of 5 average rating, 27 reviews

Private home near Hillsdale Hospital

Keep life simple at this peaceful and centrally-located home. This home is walking distance to Hillsdale Hospital, minutes from the fairgrounds, and a short drive to Hillsdale College. Make yourself at home with this family friendly retreat. This listing is for access to a private residence featuring three bedrooms, one and a half baths, as well as indoor and outdoor living, office, and kitchen spaces.

Top guest favourite
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.
Home in Hillsdale
5 out of 5 average rating, 16 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.

Top guest favourite
Two black adirondack chairs are positioned on a patio overlooking a lush green lawn. A peaceful view of colorful autumn foliage and a serene lake is visible in the background, creating a tranquil outdoor setting.
Home in Hillsdale
5 out of 5 average rating, 20 reviews

Home on Hillcrest

Conveniently located just one mile from Hillsdale College campus and within the city limits of Hillsdale, this home on Hillcrest Drive offers a scenic retreat with panoramic views overlooking Winona Lake and ever-changing wildlife. A unique mid-century ranch, it has been carefully maintained, refreshed and is ready to welcome you. You'll enjoy accommodations that are spacious, serene and inviting.

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, 279 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, 96 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.

Guest favourite
A cozy living area features a mix of seating options, including a plush gray sofa and a light-colored accent chair. A wooden coffee table rests on a neutral rug, while a television is mounted on the wall. Natural light enters through a window adorned with sheer curtains.
Home in Hillsdale
5 out of 5 average rating, 22 reviews

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. No campus construction noise!

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, 36 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, 58 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
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.
Home in Hillsdale
4.9 out of 5 average rating, 20 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.

Guest favourite
A welcoming living area is centered around a glass-top coffee table placed on an orange area rug. Comfortable seating includes a dark leather sofa and two armchairs. Natural light enters through the windows, and a ceiling fan is mounted above.
Home in Hillsdale
4.91 out of 5 average rating, 11 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.

Popular amenities for Hillsdale County house rentals