
House vacation rentals in Hillsdale County
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Top-rated house rentals in Hillsdale County
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Popular amenities for Hillsdale County house rentals
House rentals with a pool

Luxury lake-house and heated salt pool
This house was wonderful for myself, my parents, my 2 brothers, sister in law, and 2 nieces! The pool was in use from sun up to sun down. Plenty of space to spread out and relax. My mom was able to navigate between her wheelchair and walker, which meant all the world. I have stayed in many airbnbs. What sets this one apart, besides the gorgeous house, pool, and amenities, was the way everything was stocked. There were enough extra towels for all the in and outs of the pool. Anyone who has stayed at an airbnb with a pool can relate to not enough towels. Not the case here!! Also, plenty of extra toilet paper. And the good tp! How many times have I had to stop during my vacation to buy extra TP. Not at this house! It had everything I needed!! Including washing machine tabs, so I could keep up with the laundry. Tons of extra plates, silverware, cups! EXCELLENT communication from Mary. I am sure our family will be back to this Oasis!

Outdoor Oasis & Gorgeous Adrian Retreat! Welcome!
This airbnb was very spacious and clean. My family and I enjoyed this house for the weekend because we could all have our own space but gather whenever we wanted. The hosts were also very nice and friendly! Very good spot for big families.

Annie's Place behind the winery
My husband and I were looking for a weekend getaway and Annie's Place was perfect! Holly and Kirk were extremely responsive and accommodating with any requests. The place was spotless and the bed was extremely comfortable! The private, heated pool was such a treat to have available to us! We were welcomed with a basket of snacks along with a bottle of wine which was a welcoming touch. We purchased tickets for a show at the winery during our stay which was so convenient...the food and wine were so delicious! We will definitely be coming back!

Couples hot Tub 365 days a year
the vibe entering the cottage was wonderful, definitely gave the feeling of "getaway". The little carrot was each to find thanks to the clutch instructions from Judy. While we got a windy week staying by the water was calming and absolutely gave good views. I will most definitely return to The little carrot for another much needed getaway! thank you Judy!

Bent Oak Estate
We booked Bent Oak for our family to come and celebrate our wedding and it was more than we could have expected. Everyone had room to move about. Both of our dogs had plenty of room, and the outside space was so private. Daniel was always responsive and super understanding. I would recommend this to anyone who has a large group that loves to be together, his space allowed us to all do what we wanted separately while still being together. Thank you Daniel for making our wedding weekend celebration perfect!

Great Wood Lodge
We booked this place for some time away from the kids and to celebrate a couple birthdays and it was perfect!! The hot tub was lovely and the kitchen was a great place to gather and play some games and enjoy each other’s company. Fran was a great host! Super nice and made sure we felt right and home and super responsive when we had an issue and quick with a remedy. We would love to come back an again with the kids and check out the pool in the summer! Also the place smelled lovely!!
Weekly house rentals

Cozy Hillsdale Home ~ 1 Mi to Baw Beese Lake!
Charming vintage home in beautiful surroundings. Very spacious.

The Garden House
Great place to stay! We were in town for a meeting so four of us shared the house for one night. Check-in was easy, the area is cute, & it seemed very safe. The house was clean and appropriately decorated. The only drawback is the location on the main road- however, I would not let that stop me from staying here again.

Twin Spruce Craftsman
This is a wonderful place to stay in Hillsdale. We highly recommend it. The hosts are extremely thoughtful with setting up the Airbnb to bless their guests. It is a lovely home and very clean too.

The Homestead at Hillsdale (.4 miles from campus)
This was a gem of a place to stay while visiting the college. The home is clean, bright, peaceful, and beautifully decorated. What a comfort to walk into such a nicely appointed home after a long day of travel! It was an easy walk to campus and to some delicious sandwich and coffee shops. Hosts were very responsive, flexible, and kind. We would definitely recommend!

Historic Hillsdale Home Near Downtown!
Love the light that comes into the house from all the different windows as well as how open it feels inside the house.

Victorian Beauty Hillsdale College
A bunch of us old guys come in the summer for a college fundraising golf outing. we tell the same stories every year till the wee hours. the porch was perfect (we knew it would be) for the 12 or so guys and gals that come back. AC worked great and rooms were very comfortable. lots of parking too
Private house rentals

R&R friendly House
Randy and Roxy are great hosts who went above and beyond to accommodate our group and make us feel at home. I cannot recommend their cozy, cute home enough if you are visiting Hillsdale!

Firefly Cottage Lake front home on Baw Beese Lake
We enjoyed our stay at the Firefly Cottage. Everything was perfect and the view of the lake is beautiful. We hope to stay next year for our granddaughter’s birthday.

The LaFayette House (.1 miles from campus)
The house is the perfect location for visiting Hillsdale College and is charming, cozy, well equipped, spacious, well appointed in decor as well as amenities, and the host is perfectly responsive. Will always stay here!

Lovely 6Bed 4Bath Lakefront home Game Garage
Beautiful and peaceful location! The view, the space, the sleeping capacity and flexibility and the offered amenities within the price point cannot be matched. Would definitely rebook and recommend. Not only just one well stocked kitchen, but two could not be beat! Loved the large dining table in which became the focal point!

Home on Hillcrest
This home is beautiful and pristine. It’s in a quiet neighborhood, on a hill above Winona Lake. You can watch the meandering water, the water birds, deer, and other wildlife and feel the peace of this home. We’ve been lucky to stay here twice while our daughter attends Hillsdale College, and have 2 more booking for the near future. It’s our hands down favorite home away from home.

Comfy home in recreational town
Sandra's place is always great!

The Garden House
Great place to stay! We were in town for a meeting so four of us shared the house for one night. Check-in was easy, the area is cute, & it seemed very safe. The house was clean and appropriately decorated. The only drawback is the location on the main road- however, I would not let that stop me from staying here again.

Newly Renovated Home w/Backyard.
Our second time staying here. Really comfortable place; great location and super clean. We appreciated the well-equipped kitchen!
Destinations to explore
- Waterfront rentals Hillsdale County
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- Rentals with a washer and dryer Hillsdale County
- Rentals with lake access Hillsdale County
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