Vacation rentals in Hillsdale

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Top-rated vacation rentals in Hillsdale

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

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Guest favorite
A stainless steel mug featuring the words 'Bear Lake' with a bear silhouette stands on a wooden dock. In the background, a clear blue sky is visible, along with boats anchored on the shimmering lake. Lush greenery borders the water's edge.
Cottage in Hillsdale
4.94 out of 5 average rating, 82 reviews

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.

Guest favorite
Cabin in Osseo
5 out of 5 average rating, 5 reviews

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

Guest favorite
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.
Apartment in Hillsdale
4.9 out of 5 average rating, 151 reviews

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.

Top guest favorite
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.
Guesthouse in Jonesville
5 out of 5 average rating, 79 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!

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, 199 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.

Top guest favorite
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, 17 reviews

The 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 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, 284 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 favorite
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.

Guest favorite
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
4.94 out of 5 average rating, 35 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 favorite
Home in Hillsdale
4.98 out of 5 average rating, 62 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.

Top guest favorite
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
4.91 out of 5 average rating, 23 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.

Top guest favorite
Home in Hillsdale
4.95 out of 5 average rating, 20 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.

Popular amenities for Hillsdale vacation rentals

When is the best time to visit Hillsdale?

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Avg. priceG$42,021 GYDG$41,812 GYDG$42,439 GYDG$36,585 GYDG$45,784 GYDG$40,976 GYDG$37,422 GYDG$35,540 GYDG$34,495 GYDG$35,122 GYDG$38,049 GYDG$34,704 GYD
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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 house rentals in Hillsdale have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Hillsdale. Enjoy a tailored experience with all the comforts you desire.

  • 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.

  • 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 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 vacation rentals in Hillsdale

  • Total vacation rentals

    Explore 40 vacation rentals in Hillsdale

  • Nightly prices starting at

    Hillsdale vacation rentals start at G$10,453 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,900 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Hillsdale vacation 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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