Vacation rentals in Hillsdale

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Hillsdale

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favorite
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, 128 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.

Top guest favorite
A teal skoolie sits parked on a grassy area, with a shaded wood deck extending from its side. Two red outdoor chairs are positioned nearby, and decorative lights are strung overhead, adding a cozy ambiance to the serene outdoor setting.
Bus in Grass Lake
4.96 out of 5 average rating, 257 reviews

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.

Superhost
The entrance features a welcoming porch with a white picket fence. A wooden chair and a small table are positioned beside the door, while flower beds with pink and purple blooms enhance the pathway leading to the front door.
Home in East Leroy
4.91 out of 5 average rating, 165 reviews

The Sanctuary of Sonoma Lake

Kick back and relax in this calming, stylish home nestled in a quiet neighborhood. Our lovely retreat offers a relaxing getaway with a beautiful backyard featuring zen-like landscaping and ample outdoor seating. Enjoy the tranquility and find inspiration in our dedicated workspace for remote working. Just steps away from a picturesque lake, it's the perfect escape for those seeking a peaceful home away from home. Book your stay now and experience the perfect blend of comfort and relaxation.

Top guest favorite
A welcoming living room features a comfortable sectional sofa, accompanied by a decorative coffee table. A gas fireplace is seen beneath a mantle, with the word 'Relax' displayed above. Natural light enters through large windows, enhancing the cozy atmosphere.
Cottage in Grass Lake Charter Township
4.94 out of 5 average rating, 205 reviews

Clever Fox Cottage, hot tub and dog friendly

Enjoy our hot tub all year long. Canal views with free access to pedal boat, SUPs, and kayak. Relax by the indoor gas fireplace or fire pit. Guest rave about nearby wineries and walking trails. UM football : 30 miles to the Big House. Equestrians- Waterloo Hunt: 9 miles. We offer dog-friendly accommodations (pet fee required). Want a pontoon to explore the lake? Boat rental within walking distance at the end of our street. We do NOT take responsibility for third-party boat rentals.

Top guest favorite
The farmhouse is nestled among greenery, featuring a wraparound porch and a private deck extending from the upper level. The structure showcases a gable roof and a chimney, surrounded by trees and lush grass.
Farm stay in Hillsdale
4.98 out of 5 average rating, 358 reviews

Bluebird Trails

This is a rare opportunity to be the only guests on a secluded 220 acres of gentle hills with grasslands interspersed with trees and ponds. Explore natural ecosystems and witness sustainable grazing of sheep. The back yard is filled with an organic vegetable garden and behind that are honeybees. Your family may participate in any and all of it. The newly renovated apartment is the upstairs of my farmhouse. It includes a private entrance, full kitchen and deck overlooking the lake.

Top guest favorite
The exterior of the cottage features a combination of white siding and natural wood accents. Large floor-to-ceiling windows provide expansive views of the surrounding landscape. A manicured grassy area surrounds the structure, complemented by the presence of mature trees and a nearby black circular building.
Cottage in Fremont
4.97 out of 5 average rating, 185 reviews

Relaxing Cottage Near Clear Lake

Relax and unwind at our peaceful cottage at The Mill District. You will love the views out of the floor to ceiling windows. Everything inside and outside the cottage was recently remodeled including a brand new bathroom. You and your guests will love the well manicured property. Feel free to explore the grounds and bring your photographer (No sitting fee for guests). Peaceful location located next to clear lake.

Guest favorite
A hot tub is positioned on a wooden deck, overlooking a serene lake at dusk. String lights are draped above, casting a warm glow. Reflections of trees and a dock are visible on the calm water's surface, enhancing the tranquil atmosphere.
Home in Bronson
4.98 out of 5 average rating, 266 reviews

Water’s Edge-Hot Tub, Pet Friendly, No Fees

Tranquil lake living! The Water’s Edge is a great way to enjoy the lake. It is right on the water with kayaks, stand up paddle boards, and a canoe to venture out with. The hot tub accommodates 6 people. The sunroom has beautiful views as well as a couple of beds that can be used if the weather is nice. There is nothing better than falling asleep to lake sounds and a pleasant breeze! Please no college partyers.

Guest favorite
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.

Guest favorite
Home in Hillsdale
4.93 out of 5 average rating, 15 reviews

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.

Guest favorite
A functional kitchen features wooden cabinets and stainless steel appliances, including a microwave and dishwasher. A window offers natural light above the sink, with a small table and chairs visible in the foreground. The countertop is organized, enhancing the space's usability.
Home in Manitou Beach-Devils Lake
4.9 out of 5 average rating, 134 reviews

Charming Devils Lake Cottage!

Beautifully kept 2 bedroom, 2 bathroom home just steps from Devils and Round Lake. Right across from popular Highland Inn Bar and Restaurant. Close to International Speedway. Limited hotel options in the area make this lake house the perfect getaway to see friends and family! Living quarters are upstairs.

Top guest favorite
A charming white structure with a light grey roof is set against a backdrop of lush green grass and large trees. An American flag is displayed at the entrance, and a decorative stone feature is visible in the background, contributing to the property’s rustic character.
Home in Parma
4.95 out of 5 average rating, 424 reviews

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!

Top guest favorite
A scenic view of Lake James is captured from a deck, featuring lush greenery and calm waters. Outdoor seating arrangements include a round table with chairs shaded by a large umbrella, creating a welcoming space to enjoy the surroundings.
Guest suite in Angola
4.98 out of 5 average rating, 342 reviews

Cozy Kiwi - Best View of Lake James

The Cozy Kiwi is a secluded get-a-way in the heart of 101 Lakes County on Lake James, Angola, IN. Enjoy the million-dollar view from the outside decks while drinking your morning coffee, or the sunset while enjoying a glass of wine.

Popular amenities for Hillsdale vacation rentals

When is the best time to visit Hillsdale?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR3,462 ZARR3,445 ZARR3,497 ZARR3,015 ZARR3,772 ZARR3,376 ZARR3,359 ZARR3,617 ZARR3,325 ZARR3,531 ZARR3,221 ZARR3,480 ZAR
Avg. temp-2°C-1°C4°C11°C17°C22°C24°C23°C19°C13°C6°C0°C

Quick stats about vacation rentals in Hillsdale

  • Total rentals

    40 properties

  • Nightly prices starting at

    R861 ZAR before taxes and fees

  • Total number of reviews

    2.8K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

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.

  • 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.

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

    Experience the best of Hillsdale with our house rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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.

  • Do apartment rentals in Hillsdale have wifi?

    Absolutely! We offer over 10 apartment 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.

  1. Airbnb
  2. United States
  3. Michigan
  4. Hillsdale County
  5. Hillsdale