Osseo vacation rentals

We found 64 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Osseo that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the amenities you expect for your stay, which might include parking and a fireplace. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Osseo

Showing deals for:Nov 21 - Nov 28

Image gallery for Cozy home in historic Hillsdale

Exterior
10 out of 10 rating
Exceptional
(23 reviews)

Cozy home in historic Hillsdale

Hillsdale, MI

10% off
Price is CA $253
CA $2,176 total
includes taxes & fees
Cozy home in historic Hillsdale

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Find out more about Osseo

Find out more about Osseo

Why visit Osseo

  1. Scenic Lakes: Enjoy relaxing days at beautiful lakes, perfect for swimming or picnicking.
  2. Rich History: Explore historic colleges and landmarks that showcase the area's heritage.
  3. Outdoor Activities: Discover miles of trails and parks ideal for hiking and nature walks.
  4. Charming Neighborhoods: Visit nearby suburbs like Hillsdale and Litchfield for trendy shops and local cuisine.
  5. Variety of Accommodations: Choose from cozy cottages, modern apartments, or charming vacation rentals for a comfortable stay.

Popular types of accommodation in Osseo

Planning a getaway to Osseo? Discover the charm of this picturesque destination by exploring the top vacation rentals, including private homes, cozy cottages, and modern apartments. For those seeking hotel options, check out Osseo hotels and the Osseo Village Company for excellent choices. Don’t forget to read reviews to find the perfect stay, whether it's at Oak Haven or elsewhere. Start your adventure with the best accommodation available in beautiful Osseo!

  • Houses: The top choice for visitors in Osseo, offering spacious and comfortable living for families or groups.
  • Cottages: A charming option, perfect for those seeking a cozy retreat amidst nature.
  • Apartments: Ideal for solo travellers or couples, providing convenience and a home-like atmosphere.
  • Cabins: A popular pick for a rustic escape, combining comfort with the great outdoors.
  • Villas: Luxurious accommodations that cater to those wanting an upscale experience.**

Top attractions in Osseo

Osseo, Michigan, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. This charming locale boasts stunning lakes, historic colleges, and urban parks, offering plenty of opportunities for leisurely strolls and scenic views. Whether you're looking to relax at the beach or explore the area's rich history, Osseo provides a delightful blend of activities to ensure an unforgettable vacation experience for all types of travellers.

  1. Hillsdale College: A historic institution with a charming campus that boasts classical architecture and a rich cultural atmosphere. It's a great place to stroll and appreciate the beautiful surroundings.
  2. Baw Beese Lake: A picturesque lake perfect for romantic getaways, offering stunning scenery and outdoor activities. Enjoy a leisurely day at the beach or take a peaceful boat ride.
  3. Slayton Arboretum: This family-friendly arboretum features beautifully landscaped gardens and walking trails, ideal for enjoying nature and spending quality time outdoors.

Things to do recommended for families

Families visiting Osseo can explore the serene Lake Hudson State Recreation Area, enjoy the scenic beauty at Jack Tibbs Park, and relax at McCourtie Park. These nearby spots, all offering wellness and relaxation vibes, make for a delightful family getaway just a short drive from Osseo.

Things to do recommended for groups

Experience the thrill of motor racing at Michigan International Speedway and Butler Speedway, both offering exciting sports vibes. For a more relaxed outing, enjoy a round of golf at Lake Leann Golf Course, where you can soak in the beautiful outdoors with your group.

What do I need to keep in mind when booking a vacation in Osseo

When planning your trip—whether it’s with a group, family, pets, or for an extended stay—be sure to apply the appropriate filters to meet your needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Osseo with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Osseo with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, keeping in mind your closeness to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to Osseo: For many, a family getaway wouldn’t feel complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Osseo: If you're searching for vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in Osseo

Your vacation in Osseo, Michigan, promises a delightful mix of outdoor adventures and scenic beauty. Explore the charming city itself, known for its historical allure, or venture into nearby suburbs like Hillsdale and Litchfield, offering trendy shops and local cuisine. With picturesque landscapes perfect for romantic getaways, Osseo invites you to uncover its hidden gems while enjoying a blend of luxury and budget-friendly experiences. Discover the miles of trails and parks that make this region a must-visit.

  • Hillsdale: Located a mere 8.0km from Osseo, Hillsdale is a charming city that offers a blend of outdoor activities and scenic beauty. This destination is perfect for those seeking romance or a peaceful retreat. Visitors can enjoy the picturesque landscapes while exploring the local historic college and the nearby national state park. Popular activities include camping, motor racing, and educational tours. Hillsdale’s lakes also provide opportunities for relaxation and recreation, making it an ideal spot for nature lovers.
  • Pittsford: Situated just 6.4km from Osseo, Pittsford is a vibrant city known for its outdoor adventures and stunning scenery. This city attracts adventure enthusiasts with its recreational areas and campgrounds, as well as motor racing events. The local attractions include beautiful lakes and the national state park, where visitors can hike, fish, or simply enjoy the lush surroundings. Pittsford is a great place to immerse yourself in nature while experiencing the thrill of outdoor activities.
  • North Adams: Located 9.7km from Osseo, North Adams is a delightful city that promises outdoor fun and romantic getaways. With attractions such as a water park and amusement park, it is ideal for families and thrill-seekers alike. The nearby beach and lake offer perfect spots for relaxation and swimming. Whether you're looking to unwind at a resort or enjoy a day filled with excitement, North Adams provides a fantastic travel experience amidst beautiful natural landscapes.

Best time to go to Osseo

If you're planning a trip to Osseo, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January23.5°F (-4.7°C)Light RainMostly CloudyLowAverage
February25.0°F (-3.9°C)Light RainMostly CloudyLowSlightly Low
March36.1°F (2.3°C)Light RainMostly CloudyLowSlightly Low
April46.2°F (7.9°C)Light RainMostly CloudyAverageSlightly Low
May58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyHighSlightly High
July71.1°F (21.7°C)Light RainMostly SunnyHighSlightly High
August69.4°F (20.8°C)Light RainMostly SunnyHighSlightly High
September63.3°F (17.4°C)Light RainMostly SunnyAverageAverage
October51.6°F (10.9°C)Light RainMostly SunnyAverageAverage
November39.0°F (3.9°C)Light RainMostly SunnyAverageAverage
December30.4°F (-0.9°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is simple

Are you hoping to save some money on your upcoming adventure? Being open to adjusting your travel dates can be a great strategy, as prices often vary. Additionally, booking a longer stay typically leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options!

Vrbo Trips: Planning made easy

Vrbo's unique Trip Board offers you a dedicated area to plan new trips, pick up right where you left off, and manage your travel arrangements seamlessly. You can easily access properties you've saved or booked, now organized into Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Osseo getaway

Experience the unique character of Osseo with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Osseo

Do you want to find things to do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Osseo a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Lake Leann Golf Course (12.7 mi / 20.4 km)
  • Irish Hills Shore Golf Course (16.8 mi / 27.1 km)
  • Stoney Ridge Winery (25.6 mi / 41.2 km)
  • Devils Lake Golf Course (15.9 mi / 25.7 km)
  • Shaffer's Evergreen Golf Course (10.7 mi / 17.2 km)
  • DeMor Hills Golf Course (17.4 mi / 28.1 km)

Exploring the natural features in Osseo

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Osseo is a great place to get out in nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Baw Beese Lake (3.3 mi / 5.3 km)
  • Slayton Arboretum (5.5 mi / 8.9 km)
  • Fisher Lake (11.9 mi / 19.2 km)
  • Little Posey Lake (13.1 mi / 21.1 km)
  • Mackinac Island (13.2 mi / 21.3 km)
  • Lake Somerset (14.4 mi / 23.2 km)

Frequently asked questions

What is the best area to stay in Osseo when booking a vacation rental?
When considering a vacation rental in Osseo, Michigan, the most appealing area to stay in would likely be the vicinity of the charming downtown. This area offers a quaint, small-town atmosphere that superbly encapsulates the essence of Osseo. Here, you'll find a range of vacation rental options, from cosy cottages to larger family accommodations, providing a comfortable base for your stay.

One of the highlights near downtown Osseo is the picturesque Osseo Park, an ideal spot for leisurely strolls, picnics, or simply enjoying the natural surroundings. Additionally, the nearby Hillsdale County Historical Museum offers insights into the local history, showcasing fascinating exhibits that reflect the rich heritage of the region.
How much does it cost to rent a vacation home in Osseo?
Prices for vacation rentals in Osseo vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Osseo to more spacious homes.
Are there any discounts for Osseo vacation house rentals?
You can find great discounts on house rentals in Osseo on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Osseo ski resort rentals?
For ski resort rentals near Osseo, Michigan, the closest major ski area is located in the nearby town of Hillsdale, which is around a 30-minute drive away. Visitors should consider looking for accommodations in Hillsdale, where a range of properties are available to suit different preferences. Many of these rentals offer convenient amenities such as fully equipped kitchens, spacious living areas, and sometimes even outdoor decks for enjoying the surrounding natural beauty.

In Hillsdale, travellers can find cosy cabins and family-friendly lodges that provide access to both skiing and local attractions. Properties often feature essential comforts like heating, Wi-Fi, and entertainment options such as televisions or game rooms, making them ideal for relaxing after a day on the slopes.
What is the most popular type of vacation rental accomodation in Osseo?
In Osseo, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These properties typically provide spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios ideal for relaxation. Located in a quiet, rural setting, these vacation houses are well-suited for families or groups looking to escape the hustle and bustle and enjoy the natural beauty of Michigan.
Are there any family house rentals in Osseo?
In Osseo, Michigan, there are some family-friendly house rentals available, making it an appealing spot for larger groups or families seeking a getaway. Properties in this area typically provide ample space with multiple bedrooms, allowing everyone to have their own comfort. Many homes come equipped with kitchens, great for preparing meals together, as well as inviting living areas for relaxation after a day of exploring.
Can I find long-stay vacation rentals in Osseo?
A long-stay vacation rental in Osseo is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Osseo?
In Osseo, Michigan, there are several pet-friendly house rentals available, offering a great option for travellers with furry companions. Many of these properties typically feature comfortable living spaces, fully equipped kitchens, and outdoor areas where pets can enjoy the fresh air. The rentals often come with amenities such as fenced yards, making it easier for guests to relax while ensuring their pets can roam safely.
Are there any remote work vacation rentals in Osseo?
In Osseo, Michigan, there are several vacation rentals well-suited for remote work. The area offers a tranquil environment ideal for productivity, with properties that often include dedicated workspaces, high-speed internet, and comfortable living areas. Many of these rentals feature amenities such as full kitchens, allowing guests to prepare meals, and outdoor spaces for breaks in nature. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Osseo vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Osseo with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Osseo?
In Osseo, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature patios, providing a lovely outdoor space for relaxation or dining. Free Wi-Fi is commonly available in the rentals, ensuring travellers can stay connected. Additionally, some rentals come with handy appliances such as blenders and coffee makers, enhancing the convenience and comfort of the stay.
How early should I book a Osseo vacation rental?
Book your Osseo vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Osseo home rental booking on Vrbo?
To find Osseo vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Osseo vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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