Holiday rentals in Osseo

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Top-rated holiday rentals in Osseo

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Top guest favourite
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, 360 reviews

Bluebird Trails

This is a rare opportunity to be the only guests on 220 acres of gentle hills with grasslands interspersed with trees and ponds. You may explore the woodlands and wetlands as well as the sustainable grazing of sheep. The back yard is filled with an organic vegetable garden and across the yard 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 favourite
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
4.97 out of 5 average rating, 260 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.

Top guest favourite
A single-story cabin-style home features a brick facade with blue siding. Large front windows allow for natural light, while a white door serves as the main entrance. The surrounding yard, partially landscaped with grass and bare trees, offers a quiet setting.
Home in Pittsford
5 out of 5 average rating, 57 reviews

R&R friendly House

NO PETS.Relax, enjoy, Cabin like cozy feeling! 2 bedrooms, one with a queen size bed, and the other is a double. But there is a self contained air mattress, and a single folding bed, and the sofa that could accommodate a couple of smaller guest. only minutes from 2400 acres of Lost Nations State Game area, open to hunting, hiking, nature sightseeing. 12 miles from Hillsdale College . Short drive to Bundy Hill off road park. Also nearby is Hidden Lake Gardens, Irish Hills , MIS Speedway,

Top guest favourite
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, 206 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 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

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.
Flat 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 favourite
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, 186 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 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.

Guest favourite
Home in Hillsdale
4.94 out of 5 average rating, 16 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.

Top guest favourite
A modern kitchen space is highlighted by a dark wood countertop featuring a stainless steel sink and a sleek faucet. Two pendant lights hang above, illuminating the area. A framed mirror reflects the wall art in the adjacent living room, and a glimpse of the bedroom door is visible.
Home in Liberty Center
4.99 out of 5 average rating, 134 reviews

Cozy Comfortable Home in Liberty Center

Kick back and relax in this calm, recently renovated stylish house. Fully loaded with all the amenities to welcome you home. Located on the Wabash Cannoball Trail, you can hike or bike from Liberty Center all the way to Maumee. Convenient shopping nearby and just minutes off of US24, a perfect place to stay for a night, a weekend or longer!

Guest favourite
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.

Guest favourite
Flat in Jackson
5 out of 5 average rating, 8 reviews

Great 1 bed apartment near hospital / downtown!

Hi! We're Aaron and Angelina, and we're excited to share our beautiful apartment with you! We also love to travel (with our five adventurous children!), and we've stayed in Airbnb's as far away as the Middle East! We'd love to make your stay as enjoyable as possible.

Popular amenities for Osseo holiday rentals

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