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Osseo Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Osseo vacation rentals

A modern kitchen with white cabinets, stainless steel appliances, a central island with bar stools, and pendant lighting.

1. New Waterfront Guest House – Less than 10 Min to Hillsdale College

New Waterfront Guest House – Less than 10 Min to Hillsdale College
Osseo
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful and peaceful place to stay. Others should know that water is not suitable for swimming, but very relaxing to enjoy with morning coffee or evening drinks. Thanks for sharing your lovely place Teresa and Glenn"
Canada
Teresa
$303 nightly
The price is $319
Oct 12 - Oct 13
Total with taxes and fees
New Waterfront Guest House – Less than 10 Min to Hillsdale College
An aerial view of a parking lot with several cars, a large building with a dome, and surrounding buildings.

2. Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything

Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything
Hillsdale
8.6 out of 10, Excellent, (35 reviews)
"Was a great stay at a place with a lot of history! Will look to stay here again if I’m in the area!"
United States
Carter
$105 nightly
The price is $108
Oct 13 - Oct 14
Total with taxes and fees
Heart of Hillsdale Downtown Office / Kitchen / Two Beds / Close to Everything
A rustic wooden building with a red door and a window labeled "Baths".

3. Hunting Cabin Rustic Handcrafted primitive sits in our unique rustic Cowboy Town

Hunting Cabin Rustic Handcrafted primitive sits in our unique rustic Cowboy Town
Pittsford
10.0 out of 10, Exceptional, (2 reviews)
"The fishing is awesome!"
United States
Jesse
$85 nightly
The price is $85
Oct 2 - Oct 3
Total with taxes and fees
Hunting Cabin Rustic Handcrafted primitive sits in our unique rustic Cowboy Town
A bedroom with a wooden bed, a nightstand, a lamp, a chair, and a decorative wall piece.

4. Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed

Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed
Hillsdale
9.0 out of 10, Wonderful, (49 reviews)
"I have stayed here before and had great experience. There were a couple of snafoos when I arrived but everything worked out in the end. The stairs going up to my place were not ideal but I survived. I want to thank Rebecca for all her help and kindness. I want to thank the wonderful Kenton for coming down the next morning to do a great job getting my room in tip top shape. And last but not least, Scott. He came down from the Pub to reset my lock to make sure I would be completely safe. I...
United States
Michelle
$105 nightly
The price is $108
Oct 12 - Oct 13
Total with taxes and fees
Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed
A building with a gabled roof, a central window, and decorative elements including stars and a sun-like shape.

5. Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed

Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed
Hillsdale
8.4 out of 10, Very good, (29 reviews)
"On main drag so easy to fo d"
United States
debra
$100 nightly
The price is $104
Oct 8 - Oct 9
Total with taxes and fees
Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed
A rustic wooden building with a red door and a window labeled "Baths".

6. Lost Nations Cowboy Town Mining Company Cabin

Lost Nations Cowboy Town Mining Company Cabin
Pittsford
9.2 out of 10, Wonderful, (10 reviews)
"Holly is amazing. Her husband is a great help as well. I have stayed there twice now. This time was even more fun with having a horse back riding experience! We stayed for a couples night out. There were no spider webs in our cabin and we didn’t have to worry about asking for batteries for our fan! The accommodations for being a Rustic style experience were wonderful and clean. We definitely be going back."
United States
Darci
$108 nightly
The price is $113
Oct 11 - Oct 12
Total with taxes and fees
Lost Nations Cowboy Town Mining Company Cabin
A rustic wooden building with a red door and a window labeled "Baths".

7. Lost Nations Cowboy Town Bear Cabin

Lost Nations Cowboy Town Bear Cabin
Pittsford
10.0 out of 10, Exceptional, (4 reviews)
"Nice little place , full of beautiful art and scenery. Friendly host"
United States
zachary D.
$101 nightly
The price is $106
Oct 11 - Oct 12
Total with taxes and fees
Lost Nations Cowboy Town Bear Cabin
A rustic cabin with a wooden porch, a bench, and a sign indicating a deer hunting area.

8. Lost Nations Cowboy Town Riverside Cabin

Lost Nations Cowboy Town Riverside Cabin
Pittsford
9.0 out of 10, Wonderful, (12 reviews)
"A unique unforgettable stay. Friendly hosts, a sweet rescue horse, barn cats and kittens, a charming atmosphere. We had the river side cabin, which is just a short hike away. Cozy, far enough away to feel private, close enough to get visits from Midnight (a cat!)."
United States
Daphne
$110 nightly
The price is $110
Oct 11 - Oct 12
Total with taxes and fees
Lost Nations Cowboy Town Riverside Cabin
A bedroom with a bed, a mirror, and various framed pictures on the wall.

9. Heart of Hillsdale, Kitchen, Wifi, Desk, Apartment with 2 Beds Close to College

Heart of Hillsdale, Kitchen, Wifi, Desk, Apartment with 2 Beds Close to College
Hillsdale
8.4 out of 10, Very good, (29 reviews)
"Our son is a baseball player and we stay here every time we go down. Great location and price"
United States
Sue L.
$128 nightly
The price is $133
Oct 10 - Oct 11
Total with taxes and fees
Heart of Hillsdale, Kitchen, Wifi, Desk, Apartment with 2 Beds Close to College
A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a wooden entertainment unit.

10. The Howder House / Refined 1BR / Sleeps 4

The Howder House / Refined 1BR / Sleeps 4
Hillsdale
10.0 out of 10, Exceptional, (1 review)
"Hands down, this is the nicest short-term rental in Hillsdale.As a frequent visitor to Hillsdale, I’ve stayed in many places, and this one truly surpassed them all. It boasts a tiled bath, the most comfortable and cozy bed, and curated light fixtures that adjust to your touch. There’s even an espresso machine, soaps, a smart TV with Netflix and HBO memberships, and more. The laundry machine was a great touch, especially after a long travel day.Check-in, communication, and checkout were all easy...
United States
Elizabeth P.
$172 nightly
The price is $181
Oct 3 - Oct 4
Total with taxes and fees
The Howder House / Refined 1BR / Sleeps 4
A compact kitchen with a washing machine, microwave, and sink.

11. Tiny House near Hillsdale College

Tiny House near Hillsdale College
Hillsdale
10.0 out of 10, Exceptional, (1 review)
"This tiny house was exactly what I was looking for. It was clean, comfortable, and had everything I needed without feeling cramped. The space was thoughtfully laid out, and I really appreciated how peaceful it was. It was also close to get to Hillsdale College, while still giving me the feeling of being away from everything. For a quick overnight stay, it was perfect. I would definitely recommend it to anyone visiting the area who wants something a little different from a traditional hotel....
United States
Cyndi
$188 nightly
The price is $188
Oct 27 - Oct 28
Total with taxes and fees
Tiny House near Hillsdale College
A modern living room with a sectional sofa, a glass coffee table, and a painting on the wall.

12. Charming 3-bedroom house in Hillsdale near the College

Charming 3-bedroom house in Hillsdale near the College
Hillsdale
9.8 out of 10, Exceptional, (8 reviews)
"Spacious well equipped home!"
United States
Emily
$233 nightly
The price is $245
Oct 4 - Oct 5
Total with taxes and fees
Charming 3-bedroom house in Hillsdale near the College
A spacious living room with a wooden floor, a ceiling fan, a green bookshelf, a floral sofa, a white armchair, and a dining table.

13. Lake View Cottage for Two with Views of Harrison Lake

Lake View Cottage for Two with Views of Harrison Lake
Fayette
10.0 out of 10, Exceptional, (24 reviews)
"Great time, nice lake!"
United States
Athanasius G.
$183 nightly
The price is $188
Oct 5 - Oct 6
Total with taxes and fees
Lake View Cottage for Two with Views of Harrison Lake
A single-story house with a gray exterior, white trim, and a number '2907' on the door.

14. Entire Home with Lake Access - Cozy Cove at Manitou

Entire Home with Lake Access - Cozy Cove at Manitou
Manitou Beach-Devils Lake
9.8 out of 10, Exceptional, (29 reviews)
"Nice place for our needs"
United States
Jason C.
$199 nightly
The price is $204
Oct 4 - Oct 5
Total with taxes and fees
Entire Home with Lake Access - Cozy Cove at Manitou
A modern kitchen with white cabinetry, a stainless steel range hood, a built-in oven, a dishwasher, and a window providing natural light.

15. Cozy home in historic Hillsdale

Cozy home in historic Hillsdale
Hillsdale
9.8 out of 10, Exceptional, (40 reviews)
"Great home close to downtown and the college. Very convenient."
United States
Laura B.
$412 nightly
The price is $427
Oct 4 - Oct 5
Total with taxes and fees
Cozy home in historic Hillsdale
A covered porch with two chairs and a table, a lattice screen, and a potted plant.

16. Private home near Hillsdale Hospital

Private home near Hillsdale Hospital
Hillsdale
$309 nightly
The price is $309
Oct 2 - Oct 3
Total with taxes and fees
Private home near Hillsdale Hospital
A compact kitchen with a washing machine, dishwasher, and a window with blinds.

17. Modern home in Hillsdale walking distance to Hillsdale College

Modern home in Hillsdale walking distance to Hillsdale College
Hillsdale
$394 nightly
The price is $409
Oct 4 - Oct 5
Total with taxes and fees
Modern home in Hillsdale walking distance to Hillsdale College
A cozy cabin interior with a wooden ceiling, a fireplace, a sofa, and a dining area.

18. Cabin, rustic elegance w/ hot tub, lake access

Cabin, rustic elegance w/ hot tub, lake access
Clarklake
9.8 out of 10, Exceptional, (129 reviews)
"Had a wonderful stay"
United States
Daniel H.
$209 nightly
The price is $209
Oct 8 - Oct 9
Total with taxes and fees
Cabin, rustic elegance w/ hot tub, lake access
Dining area and living room view from kitchen

19. Enjoy fall colors without leaving the deck

Enjoy fall colors without leaving the deck
Brooklyn
10.0 out of 10, Exceptional, (1 review)
"Beautiful property. Very clean and comfortable. Had everything we needed. The lake was gorgeous. Absolutely loved kayaking, finding the canals and exploring the connected lakes."
United States
Anonymous traveler
$357 nightly
The price is $376
Oct 2 - Oct 3
Total with taxes and fees
Enjoy fall colors without leaving the deck
A two-story house with a balcony, a garage, and a well-maintained garden.

20. Relax, Paddle, Bonfire, take in the fall colors.

Relax, Paddle, Bonfire, take in the fall colors.
Brooklyn
10.0 out of 10, Exceptional, (5 reviews)
"What a fantastic stay! It’s close to everything but secluded enough to relax and unwind. The hosts were great. Communication was excellent. We enjoyed dinner on the deck and relaxing while overlooking the water afterwards. If you’re looking for some R&R, this place won’t disappoint!"
United States
Kerry S.
$357 nightly
The price is $376
Oct 2 - Oct 3
Total with taxes and fees
Relax, Paddle, Bonfire, take in the fall colors.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osseo Hotel Reviews

Sauder Village Heritage Inn

Sauder Village Heritage Inn

8/10 Good
"This was a unique place to stay. I wish I had known that the village was going to be closed on Sundays, since that was the only day we would have been able to tour the village. We enjoyed the pool and hot tub. The restaurant on site was pricey for the food available."
Amy 3-night trip
Posted 4 hours ago
Sauder Village Heritage Inn

Find out more about Osseo

Everything you need to know about Osseo vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osseo vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osseo vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osseo vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osseo. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osseo in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $188 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osseo rentals

At Expedia, we put the best Osseo vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osseo rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osseo vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osseo. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Osseo?

Yes, we offer vacation rentals near popular sights in Osseo, or you can choose a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Osseo?

Cozy Lakefront Getaway with 3 kayaks, in Hillsdale County, Bird Lake Michigan.: Visitors give good reviews to this Osseo vacation home rental, which is located on a lake and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Osseo?

Expedia has 3 vacation rentals for your stay in Osseo.

What’s there to see and do in Osseo?

Baw Beese Lake and Bird Lake are a couple of lovely local spots to get outside and enjoy nature. Hillsdale College and Hudson Museum are a couple of places you'll find in the larger area.

What’s a vacation rental in Osseo like?

Vacation rentals are private properties where you can stay for several days or longer in Osseo. Vacation rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.