Vacation rentals in Osseo

5.0 out of 5 average rating, 5 reviews

The Independence Inn near Hillsdale College

Welcome to Independence Inn, the premier founding-era themed stay near Hillsdale College. This recently renovated home was thoughtfully designed around America's founding spirit, featuring curated historical décor, premium furnishings, luxury bedding, and elevated finishes throughout. Professionally managed by Hillsdale College graduates and hospitality professionals, Independence Inn delivers exceptional cleanliness, premium comfort, and true local hospitality from a team that knows Hillsdale.

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A living room area features a stone fireplace, which is complemented by a wooden mantel displaying a clock and a decorative item. Sunlight streams in, highlighting a nearby bookshelf and a vintage wooden cabinet, creating an inviting scene.

5.0 out of 5 average rating, 12 reviews

The Lake Cottage

Welcome to your perfect getaway. This quiet and comfortable, two bedroom home offers the ideal balance of relaxation and adventure. The Lake Cottage is located right on Lake Baw Beese and is perfect for families, couples, or friends looking to unwind and explore Hillsdale, Michigan. Whether you’re here to kayak, grill, or just enjoy a mug of coffee and breathe in the fresh air from one of our porches, this home is your base for a peaceful and beautiful day. 3.4 miles from Hillsdale College.

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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.

4.96 out of 5 average rating, 119 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.

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5.0 out of 5 average rating, 71 reviews

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

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,

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4.92 out of 5 average rating, 36 reviews

A serene lakefront view showcases a wooden dock extending into the calm water, surrounded by trees and green grass. In the background, a cozy home is visible, featuring a covered porch and large windows. The reflection of the structures and trees is mirrored in the lake.

Home in Osseo

Cozy Lakefront Home minutes from Hillsdale College

Welcome to our lakefront home on Bird Lake—where relaxation, comfort, and fun come together. Nestled directly on the shoreline, this beautifully updated retreat offers breathtaking views, direct water access, and remodeled living spaces, making it an ideal escape for families, couples, or friends. Begin each day with stunning sunrises and unforgettable views from your private deck. Inside, the remodeled main living area features an open floor plan designed to keep everyone connected.

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Cottage in Manitou Beach-Devils Lake

4.99 out of 5 average rating, 102 reviews

Lakefront Getaway: Private dock, HOT TUB & kayaks

DEVILS LAKE GOLDEN RETREAT We are located directly on the lake with no walk to the water. Charming Cottage with one of the most spectacular views of the lake! The sunrises, sunsets, and calming sounds of the water will have you never wanting to leave. A gorgeous place to relax, unwind and enjoy every season of beautiful Devils Lake. Ideal for a couples getaway, girls weekends, or family vacation You may bring a boat or rent one. We have 2 kayaks available for your use.

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4.98 out of 5 average rating, 55 reviews

The exterior of Frogmore Cottage features a welcoming deck with handmade Adirondack chairs overlooking the surrounding greenery. Bright kayaks are stacked beside the cottage, ready for use. The driveway runs alongside, providing parking access. A neatly landscaped area enhances the cottage's inviting exterior.

Cottage in Hillsdale

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!

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4.85 out of 5 average rating, 138 reviews

A waterfront cabin is depicted with a large glass front, allowing ample natural light inside. Lush green grass surrounds the house, complemented by tall trees. A pathway leads to a spacious deck area with outdoor seating and a grill, enhancing outdoor relaxation opportunities.

Home in Coldwater

Coldwater Lake Waterfront Cabin - Boat for Rent

Relax with the whole family at this peaceful waterfront lakehouse, with walk-in, sandy beach lake access. Boat available to rent, and space available for your boats. Spacious yard with plenty of parking. Coldwater Lake is over 1,600 acres of all-sports fun on desirable South Chain of Lakes in Coldwater, MI. The chain is 17 miles, traversable via pontoon or speedboat! The Cabin includes 3 bedrooms and 2.5 baths.

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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.

4.89 out of 5 average rating, 295 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.

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4.98 out of 5 average rating, 108 reviews

A charming white house is framed by vibrant autumn leaves falling to the ground. The front porch features two rocking chairs, and a red door creates a warm focal point. A pathway leads to the entrance, surrounded by a carpet of colorful leaves.

Home in Jonesville

The Rupp House

Make your Hillsdale County home base in one of the earliest houses in Jonesville, conveniently located 10 minutes from Hillsdale College. The house is a solid preserved house which invites you to kick off your shoes and relax. It has a full kitchen, a large dining table and beds for 6 persons. There is one bathroom which has a shower and plenty of hot water. Full kitchen. Washer and dryer.

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4.99 out of 5 average rating, 81 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.

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