Holiday houses in Hillsdale

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Top-rated holiday rentals in Hillsdale

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

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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.

Top Guest favourite
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.
Home in Hillsdale
4.96 out of 5 average rating, 102 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.

Guest favourite
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.
Home in Hillsdale
4.75 out of 5 average rating, 315 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.

Top Guest favourite
A spacious kitchen area features wooden cabinetry and modern appliances. An island with a countertop is positioned at the center, while a dining table with four chairs is situated nearby. Soft natural light illuminates the room, enhancing the neutral color palette.
Guesthouse in Jackson
4.98 out of 5 average rating, 100 reviews

Quiet Home Away from Home!

Forget your worries in this spacious and serene space. Quiet, safe, and outside city limits. Private entrance and dedicated heating and cooling. Electric fireplace for cold nights. Queen size bed and full size pull out couch. Smart TV in Living Room and Bedroom. Work desk, PC, and printer for your use. Fully stocked kitchen with all appliances and utensils. Walk in shower, stackable washer and dryer, and walk-in closet. Entire property is handicap accessible.

Guest favourite
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

Top Guest favourite
Cottage in Hillsdale
4.98 out of 5 average rating, 45 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 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.

Guest favourite
Tiny home in Hillsdale
5 out of 5 average rating, 6 reviews

Charming Tiny Home Retreat

Charming tiny home retreat nestled in the trees near Hillsdale College. Enjoy a peaceful setting with a farm view and local wildlife. Features include a kitchenette, 7.5 cu ft fridge, washer and dryer combo, tub/shower, fire pit, and bistro set. Thoughtful touches like fire starters, snacks, and a semi-stocked fridge make it easy to settle in. Ideal for solo travelers, couples, or anyone craving a quiet, cozy getaway.

Top Guest favourite
A raised treehouse structure is surrounded by tall pine trees in a woodland clearing. Two wooden Adirondack chairs are positioned on the ground, facing the entrance with green doors. A staircase leads up to the deck, providing access to the elevated space.
Treehouse in East Leroy
5 out of 5 average rating, 689 reviews

Outpost Treehouse

The lookout inspired Outpost Treehouse (not actually attached to a tree) sits in a white pine forest in the middle of a 50 acre active farm. The 15 hand crafted windows allow for great views watching out for Michigan wildlife--White tail deer, turkeys, owls, coyote have all been spotted from the elevated wrap around deck. The biggest regret that guests have noted is “we wish we would have stayed longer”!

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.

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
4.96 out of 5 average rating, 114 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 exterior of a single-story home features large, dark-framed windows and a decorative arched window above the entrance. A well-maintained lawn is surrounded by trees, providing a serene backdrop. A small bush is planted near the front door.
Apartment in Hillsdale
5 out of 5 average rating, 34 reviews

wildlife sanctuary 3 bed 2 bath Townhouse

This stylish place to stay is perfect for group trips. Fully equiped kitchen with washer and dryer. Three bedroom{2 king 1 queen} 2 bath. king master suite with jacuzzi tub and stand up shower. Master also has sliding glass doors that lead to a small deck. Comfortable Living /dining space with gas fireplace. Attached two car garage.

Popular amenities for Hillsdale holiday rentals

When is the best time to visit Hillsdale?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$341 NZD$340 NZD$345 NZD$297 NZD$372 NZD$333 NZD$304 NZD$289 NZD$280 NZD$285 NZD$309 NZD$282 NZD
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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.

  • Are there family-friendly vacation rentals in Hillsdale?

    Hillsdale has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Hillsdale with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Hillsdale have air conditioning?

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

  • 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 House Rentals in Hillsdale?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with air conditioning, 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 $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,690 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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