Osseo Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Osseo holiday 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

Osseo

Teresa

HK$2,283 total

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a wooden bed, a nightstand, a lamp, a chair, and a decorative wall piece.

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

Hillsdale

"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...

Michelle

HK$700 total

includes taxes & fees

15 Nov - 16 Nov

An aerial view of a parking lot with several cars, a large building with a dome, and surrounding buildings.

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

Hillsdale

Carter

HK$730 total

includes taxes & fees

11 Nov - 12 Nov

A building with a gabled roof, a central window, and decorative elements including stars and a sun-like shape.

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

Hillsdale

Kelleigh R.

HK$770 total

includes taxes & fees

11 Nov - 12 Nov

A compact kitchen with a washing machine, microwave, and sink.

5. Tiny House near Hillsdale College

Hillsdale

Kerry L.

HK$1,597 total

includes taxes & fees

5 Nov - 6 Nov

A modern living room with a sectional sofa, a glass coffee table, and a painting on the wall.

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

Hillsdale

Emily

HK$2,037 total

includes taxes & fees

5 Nov - 6 Nov

A modern living room with a flat-screen TV, a dining table, and a sofa.

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

Hillsdale

Courtney H.

HK$1,357 total

includes taxes & fees

5 Nov - 6 Nov

A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in dishwasher, and a coffee maker on the countertop.

8. Close to Hillsdale College in a modern home with dedicated work space

Hillsdale

Traci S.

HK$3,135 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinetry, a stainless steel range hood, a built-in oven, a dishwasher, and a window providing natural light.

9. Cozy home in historic Hillsdale

Hillsdale

Laura B.

HK$3,186 total

includes taxes & fees

5 Nov - 6 Nov

A covered porch with two chairs and a table, a lattice screen, and a potted plant.

10. Private home near Hillsdale Hospital

Hillsdale

HK$2,197 total

includes taxes & fees

15 Nov - 16 Nov

A two-story house with a porch, surrounded by greenery.

11. The Independence Inn near Hillsdale College: The Premiere Themed Stay

Hillsdale

HK$2,167 total

includes taxes & fees

8 Nov - 9 Nov

Two Adirondack chairs facing a grassy area with trees in the background.

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

Fayette

Kevin

HK$1,500 total

includes taxes & fees

9 Nov - 10 Nov

A cozy cabin interior with a wooden ceiling, a fireplace, a sofa, and a dining area.

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

Clarklake

Stephanie J.

HK$1,569 total

includes taxes & fees

11 Nov - 12 Nov

A compact kitchen with a washing machine, dishwasher, and a window with blinds.

14. Modern home in Hillsdale walking distance to Hillsdale College

Hillsdale

HK$2,927 total

includes taxes & fees

15 Nov - 16 Nov

A two-story house with a covered porch, a brick chimney, and a small deck.

15. Turtle Cove Lakefront APT. 10 min from MIS, 40 min to Ann Arbor

Clarklake

Shannon T.

HK$1,664 total

includes taxes & fees

9 Nov - 10 Nov

Dining area and living room view from kitchen

16. Quiet Lake Mornings – Cozy Irish Hills Cabin

Brooklyn

Anonymous traveller

HK$3,060 total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a balcony, a garage, and a well-maintained garden.

17. Lakeside Sunrises & Starry Nights – Meadow Lake

Brooklyn

Kerry S.

HK$3,060 total

includes taxes & fees

5 Nov - 6 Nov

A spacious living area with a large sectional sofa, a dining table, and multiple windows offering views of a backyard.

18. Brand-New Lakefront Retreat on Nettle Lake Swim, Fish & Relax

Montpelier

Madisen Y.

HK$4,828 total

includes taxes & fees

5 Nov - 6 Nov

A spacious living room with a large window overlooking a lake, furnished with a sofa, chairs, and a dining table.

19. Large Lakefront Retreat – New Hot Tub!

Manitou Beach-Devils Lake

Renee S.

HK$5,485 total

includes taxes & fees

5 Nov - 6 Nov

A covered outdoor seating area with a table, chairs, and a sofa with blue cushions.

20. Waterfront lake cottage on gorgeous Clark Lake in Jackson! 4 bedrooms, sleeps 10

Clarklake

Brent

HK$4,806 total

includes taxes & fees

5 Nov - 6 Nov

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Top Osseo Hotel Reviews

Holiday Inn Express & Suites Montpelier by IHG

8/10 Good

"The only complaint I have was with the odor from nearby farms. It wasn’t noticeable in the hotel. Other than that, the room, pool, and hotel were nice and clean. The breakfast selection was great and nice variety to pick from."

Cozy Lakefront Getaway with 3 kayaks, in Hillsdale County, Bird Lake Michigan.

10/10 Excellent

"This property is perfect for a Hillsdale College parent visit, an easy drive to the school. The place is incredibly charming and really makes you feel at home. The sun porch is cozy and you can’t beat the view with the lake!Patti is clear and thorough in her communication, which I appreciate! The TV was super easy to use, too."

Lakefront Winter Getaway – Fireside Nights

10/10 Excellent

"The property is a small cabin on a lake. It is in a quite, peaceful community. We were in town for a wedding so we only stayed 2 nights in the fall. We didn't enjoy any water activities while we were there, but it appeared that the owner provides nice amenities for people that do. Seating is a little limited. One 3 seater couch and one 4 person table. It worked for our party of 4, but if you have a larger party, it could be tight. There is additional seating on the patio/decks, but it was pretty chilly while we were there.There is packing across the street from the cabin which is easily accessible. The hosts were responsive and easy to work with."

Waterfront lake cottage on gorgeous Clark Lake in Jackson! 4 bedrooms, sleeps 10

8/10 Good

"Living room small for 10 people. Bed rooms ok. Small front yard. Watch the sun come up view. nice long dock with chairs at the end. Walking distance from restaurant. Well-equipped kitchen."

Find out more about Osseo

Search for holiday rentals in Osseo on Expedia! You can easily find your home rentals, villas, holiday apartments in Osseo using one of the methods below:

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Frequently asked questions

Are there holiday rentals in Osseo?

Yes, there are holiday rentals close to the most popular sights in Osseo, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osseo has to offer?

Cozy Lakefront Getaway with 3 kayaks, in Hillsdale County, Bird Lake Michigan.: This highly rated holiday home rental in Osseo is located on a lake, and has a patio, a private garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Osseo?

Expedia has 3 holiday 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 wider area.

What’s a holiday rental in Osseo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osseo. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.

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Check prices for these dates

Our top choices for Osseo holiday rentals

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

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

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

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

5. Tiny House near Hillsdale College

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

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

8. Close to Hillsdale College in a modern home with dedicated work space

9. Cozy home in historic Hillsdale

10. Private home near Hillsdale Hospital

11. The Independence Inn near Hillsdale College: The Premiere Themed Stay

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

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

14. Modern home in Hillsdale walking distance to Hillsdale College

15. Turtle Cove Lakefront APT. 10 min from MIS, 40 min to Ann Arbor

16. Quiet Lake Mornings – Cozy Irish Hills Cabin

17. Lakeside Sunrises & Starry Nights – Meadow Lake

18. Brand-New Lakefront Retreat on Nettle Lake Swim, Fish & Relax

19. Large Lakefront Retreat – New Hot Tub!

20. Waterfront lake cottage on gorgeous Clark Lake in Jackson! 4 bedrooms, sleeps 10

Find holiday rentals that suit your style

Top Osseo Hotel Reviews

Holiday Inn Express & Suites Montpelier by IHG

Sauder Village Heritage Inn

Hillsdale College Dow Hotel and Conference Center

Cozy Lakefront Getaway with 3 kayaks, in Hillsdale County, Bird Lake Michigan.

Lakefront Winter Getaway – Fireside Nights

Bryan Inn

# Private Indoor Pool # Sleeps 25

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

Waterfront lake cottage on gorgeous Clark Lake in Jackson! 4 bedrooms, sleeps 10

Find out more about Osseo

Frequently asked questions

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