Holiday rentals in Osseo

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Top-rated holiday rentals in Osseo

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Top guest favourite
A modern tiny house is set within a lush green yard, featuring wooden siding and a metal roof. Large windows provide views of surrounding trees and landscaping. Decorative stones and plants enhance the outdoor space, while a wooden deck offers an entryway to the home.
Tiny home in Black River Falls
4.97 out of 5 average rating, 452 reviews

Tiny on the River

According to Forbes, Escape makes "the most beautiful tiny houses in the world". Ours is perched near our home above the Black River. It's a quiet neighborhood just minutes from the interstate, parks, trails, and our vibrant downtown with cafés, shops, and great restaurants. Enjoy privacy and breathtaking views from the enormous windows or the cozy daybed on the porch! Deer, beaver, eagles, and more make frequent cameos as the seasons paint shifting riverscapes and astonishing sunsets. *No Pets

Guest favourite
A cozy living space is featured, with a pale sectional sofa and a brown vintage couch positioned around a patterned area rug. A wood stove sits against a wall, and large windows offer natural light, framed by soft drapes. Decorative accents enhance the warmth of the room.
Home in Osseo
4.93 out of 5 average rating, 160 reviews

The Hogstad Homestead

The Hogstad Homestead has been in our family for nearly 70 years. The name is in honor of my great grandparents Ardell&Elaine Hogstad who bought the property in the early 1950's. They raised their two children there and also operated a farm for many years. Since then it has been home to many family members. In 2017 my husband & I had the opportunity to buy it. It was home to us for 5 amazing years where we created many happy memories. We are now ready to share this special property with others!

Top guest favourite
A modern kitchen features a sleek marble island at its center, surrounded by wooden chairs. Stylish pendant lights hang above a stainless steel stove, complementing the black cabinetry. Large windows allow natural light to fill the space, enhancing the functional layout.
Home in Chippewa Falls
4.99 out of 5 average rating, 264 reviews

Duncan Creek House

Contact me if you’d like a longer term stay and I’ll open up more dates in January, February,March & April. This is a cozy house located on Duncan Creek where you’ll hear the lovely sound of rushing water and will likely spot some eagles. It is located within walking distance of Leinie’s Lodge, Irvine Park, Olson’s Ice Cream Parlor and local hiking/bike trails. Dogs are welcome. The cancellation policy is set as “Strict”, but I’ll give full refunds if you cancel at least 14 days in advance.

Top guest favourite
A cozy living area features a large blue sectional sofa and a comfortable brown armchair. A wooden coffee table is centered on a patterned area rug. Natural light enters through the window, adorned with white curtains, illuminating the space.
Home in Eau Claire
4.98 out of 5 average rating, 142 reviews

WanderInn Riverview

Nestled in a peaceful cul-de-sac, our cozy retreat offers the perfect getaway! Conveniently located near key thoroughfares, you're just minutes from public boat landings, beaches, parks, scenic bike trails, and downtown Eau Claire, making it easy to explore the area. Thoughtfully decorated with comfort in mind, our home provides a relaxing space to unwind. We take pride in using non-toxic cleaning products, ensuring a safe and eco-friendly stay. The ideal base for both relaxation and adventure!

Guest favourite
A bright living area features a comfortable couch with yellow accents and a decorative area rug. Large windows allow natural light to fill the room, offering views of the surrounding greenery. Wall art adds a touch of color to the light-toned walls.
Guest suite in Hixton
4.9 out of 5 average rating, 309 reviews

A Suite Getaway

You'll love this place because of the spectacular views, horses, wildlife, fishing, hiking and hot tub for relaxing, a romantic getaway or simply just girl time. This spot is perfect for couples or solo adventurers! A unique suite is attached to an elegant vintage peg barn. Space for bringing horses, snowmobiles or ATV's since we have trails. A mile away from snowmobile trails and 25 mins from a State Park. Also, perfect for snowshoeing and cross country skiing. Fire pit available.

Top guest favourite
A spacious two-story building is shown with a metal roof and a welcoming front porch. Colorful hanging flower planters add vibrancy, and outdoor seating is arranged near the entrance. The surrounding grassy area offers a relaxed, natural setting.
Guest house in Hixton
4.96 out of 5 average rating, 133 reviews

Country Retreat. Beautiful sunsets and sunrises.

Fresh country air. Beautiful view. Cable TV. Wi-Fi. Hot Tub (chemical free). Spacious furnished kitchen. Sectional sofa with recliners. Recliner. Electric fireplace. Outdoor firepit (bring your own wood). Washer and dryer. 12 inch step into tub/shower. This beautiful getaway is attached to the family business shop. We do load trailers occasionally and will be working in shop at times. Minimal noise. 30 Minutes from Eau Claire. We are only 25 minutes from two lakes with beaches.

Top guest favourite
A cozy living room features a plush green sofa adorned with decorative pillows. A wooden coffee table sits in front of the seating area. A recliner is positioned nearby, and a warm light illuminates a rustic wood accent wall, creating a comfortable atmosphere.
Place to stay in Whitehall
4.96 out of 5 average rating, 142 reviews

A cozy shed house located in the rolling hills.

A cozy shed house located in the hills of Coral City, WI. This Shed house includes a private deck, cozy living room, full kitchen, 1 bedroom with queen bed, 1 bathroom with shower and extra air mattresses, sheets, & pillows for guests. It is surrounded by nature but near to the city. We are also located close to many wedding venues. The Shed House is a separate building, but located on the same property as the owner's home. During the winter months, 4-wheel drive is necessary.

Top guest favourite
A peaceful view reveals a calm pond surrounded by lush greenery, with tall trees and a clear blue sky reflecting off the water's surface. Comfortable outdoor seating and a decorative lantern are positioned on a wooden deck, inviting relaxation.
Cabin in Neillsville
4.95 out of 5 average rating, 139 reviews

Cheerful 2 bedroom cabin with hot tub and pond

This home is just minutes from Lake Arbutus, which has beaches, ATV trails, fishing, boating, swimming, hunting areas and much more. Direct access to ATV/UTV and snowmobile trails! 2 bedrooms with queen size beds; and 1 king bed, 1 queen bed and futon in loft. Kayak and fishing poles for use on the pond or at nearby Lake Arbutus! UTV rental available on site. We do have 1 4 passenger 2024 can-am maverick available at $299/day. Inquire at time of booking for availability.

Guest favourite
A cozy living room offers a relaxing space with a light blue sofa and a white sectional. Natural light fills the room through a window, and a wooden coffee table sits in the center, complemented by a decorative basket nearby.
Home in Eau Claire
4.8 out of 5 average rating, 769 reviews

The Mulberry Loft | Cozy 2BR Near Downtown EC

Set in a charming house built in the 1800s, this cozy getaway is just 4 minutes from downtown Eau Claire and 7 minutes from UW-Eau Claire. With two inviting bedrooms, you'll enjoy a blend of historic charm and modern comfort. Perfect for couples, families, or solo travelers, this serene spot offers easy access to local attractions while providing a peaceful escape. Experience the unique character of Eau Claire from this delightful vintage home!

Top guest favourite
A rustic red barn-style structure is surrounded by snow-covered trees, creating a serene winter scene. The building features white accents and a porch area, with snow blanketing the ground and clinging to the branches of nearby trees.
Guest house in Whitehall
4.96 out of 5 average rating, 144 reviews

The Granary Guesthouse @ Harvest Home Farm

Harvest Home Farm is located at the end of a dead end road nestled in a valley, just 4 miles northeast of Whitehall, Wisconsin, in beautiful Trempealeau County. The 160 acre farm has a long term focus on raising grass fed sheep and poultry. We also have a produce garden, a berry patch, and an apple orchard. The farm has 80 acres of mixed hardwoods and softwoods and an abundance of wildlife as well as a network of walking trails.

Guest favourite
A cozy living area is presented, featuring a dark sofa paired with a light patterned rug. Natural light enters through multiple windows, enhancing the neutral grey walls. A small table stands in the center, while decorative elements add a touch of warmth to the space.
Home in Eau Claire
4.86 out of 5 average rating, 161 reviews

Cute and cozy tiny home close to downtown EC

This 1 bedroom, 1 bathroom tiny home close to downtown Eau Claire is cozy, stylish, and has everything you need! Make yourself at home in our tiny boho-chic oasis. If you want to be in the heart of Eau Claire, this is the place for you! We're located less than 5 minutes from downtown, bars, restaurants, shopping, and all amenities. We're pet-friendly, but please note that we charge a $25 pet fee per pet.

Top guest favourite
The exterior of the log cabin features a spacious wooden balcony with a railing. A swing hangs near the entrance door, while large windows adorn the upper area, inviting natural light. The structure is surrounded by wooded scenery, emphasizing its secluded location.
Cabin in Neillsville
4.95 out of 5 average rating, 172 reviews

Secluded Cabin near the East Fork!

Cozy log cabin on 40 private wooded acres with a south facing wall of windows to enjoy looking at the outdoors. Its off the beaten path, but five miles from the recreational hub of Hatfield, WI and the Black River Forest. We offer a private cabin for up to 4 guests. South Enjoy the outdoors: hiking, canoe/kayaking, ATVing, XC and downhill skiing, hunting, fishing, mountain biking etc.

Popular amenities for Osseo holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Trempealeau County
  5. Osseo