Holiday rentals in Osseo

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Top-rated holiday rentals in Osseo

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Robinson Creek meanders gently, bordered by a stunning rock face and wooded banks adorned with evergreen trees. The rocky shoreline provides a serene backdrop for nature enthusiasts, with a calm water surface reflecting the surrounding landscape.
Cabin in Black River Falls
4.92 out of 5 average rating, 290 reviews

Peaceful Cabin Nestled on Robinson Creek

Get away among the sights, sounds, and smells of nature at the Fat Porcupine Cabin in Black River Falls. Robinson Creek runs along the back of the property below a stunning rock face. The sandy shore is the perfect place to relax. The home sits on a 2.5 acre wooded lot filled with aromatic evergreens. The cabin is ideal for couples looking for a cozy quiet retreat, and there's also plenty of sleeping space for families or groups to make many happy memories. We hope you make yourself at home!

Top guest favourite
A wooden sauna is positioned in the center of a rustic room with exposed beams and corrugated metal walls. Two wooden rocking chairs sit nearby. Light enters through several windows, and a basket is placed on the floor, enhancing the inviting, serene environment.
Home in Stockholm
4.96 out of 5 average rating, 274 reviews

Bogus Valley Holm Country/Farm Pepin/Stockholm

Come to the country and enjoy lodging at quiet Bogus Valley Holm. Located in picturesque Bogus Valley, between Pepin and Stockholm Wisconsin. This vintage home farmstead on 4 acres, was built in the mid 1850s and has old world character architecture with the comforts of modern day amenities. The southern exposure enclosed front porch is the favorite gathering spot for most everyone that has stayed in the home. This 2 bedroom 1 1/2 bath property has potential for sleeping up to 8 guests.

Guest favourite
An aerial view of the living space highlights wood-paneled walls and natural light from multiple windows. A comfortable sofa faces a wood stove, while blue accent chairs are positioned nearby. A dining table and clock are visible, complementing the open layout.
Home in Chippewa Falls
4.95 out of 5 average rating, 305 reviews

Moon Bay Getaway: 2BR on Lake Wissota with Hot Tub

Come stay on a calm and quiet section of the lake. This newly renovated home on Lake Wissota makes for the perfect lake getaway any time of year. Our 2 bedroom, 1.5 bath home comes with a full kitchen, a deck overlooking the lake, private dock, fire pit, 2 queen beds, a hot tub, and a 4 season room. Explore Lake Wissota State Park or tour the Leinie Lodge. If you want to get out on the water, canoe, kayaks and paddles are included. Chippewa County Zoning Permit #09-ZON-20200667

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, 135 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, 151 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.

Top guest favourite
A well-appointed interior space features a cozy sleeping area with a light-colored bed and natural wood accents. A small dining table is set with plates and candles, while a comfortable seating area includes a leather couch adorned with a green throw pillow. Large windows offer views of the surrounding woods.
Tiny home in Elroy
4.96 out of 5 average rating, 186 reviews

Emerald Little Lodge Overlooking Woodland Pond

Check out Opal Little Lodge also! - - - - - - - - - - - - - - - - - - - - - This cozy modern little lodge designed and built by Wisconsin Tiny Homes, is tucked into the woods 150 ft above a small woodland pond in the valley below. A bird lover's paradise. Comfortably and thoughtfully appointed, it's the perfect getaway to enjoy with a companion or as a solo retreat. Immerse yourself in nature and treat yourself with luxurious accommodations and private hiking trails.

Guest favourite
A spacious modern barn-style cabin is depicted against a clear blue sky. A well-maintained grassy area surrounds the structure, featuring multiple windows and a basketball hoop mounted on the side. Two cupolas adorn the roof, contributing to the building's distinct character.
Barn in Peterson
4.96 out of 5 average rating, 113 reviews

Big Buck Inn

Brand new heating and air unit installed in 2025! Cabin is upstairs in a modern barn. Beautiful panoramic views. Spacious 2 BR/1 BA open concept with a full kitchen. Country cottage decor combined with an avid sportsman's touch. Patio with a bonfire area & private grill. Minutes to trout streams, dining, shopping, bike trail, Lanesboro and Peterson. Enjoy the morning turkey gobbles, pheasant kackles, or the afternoon visit of a whitetail deer strolling through!

Guest favourite
A spacious bedroom features a wooden ceiling and warm-toned walls. A large window allows natural light, while a cozy quilt covers the bed. A decorative rug is placed on the wooden floor, and a dresser with a mirror adds functional charm to the room.
Cabin in Hixton
4.91 out of 5 average rating, 546 reviews

Living Waters Cabin Getaway

Stunning 92 acre property. Fishing, swimming, hiking, biking, birding, campfires all in an atmosphere of the great outdoors. Spacious bedroom overlooks acres of wooded scenery and landscapes of the rolling hills of Western Wisconsin. Owners home is located approx. 200 ft from cabin. A 2.5 car garage separates buildings. Second Airbnb is located approximately 200 feet from Cabin however no shared areas and completely private and separate from each other.

Top guest favourite
The exterior of the log home is showcased, surrounded by tall pine trees. A deck extends alongside the house, offering views of the lake, which is visible in the background. Outdoor seating, including several wooden chairs, is positioned near the water's edge among fallen leaves.
Home in Augusta
4.95 out of 5 average rating, 263 reviews

Stunning Lakefront Home-Private Beach & Much More!

This beautiful log home is just steps away from the lake and has 100 feet of private beach and a large dock to relax on! Whether you are looking for a retreat in winter, spring, summer or fall - - this unique treasure has it ALL! Use of a kayak, canoe and stand-up paddleboard included in summer. Use of ice skates included in winter. This gem of a property is also dog friendly! Perfect place for a business team getaway as well.

Top guest favourite
A stylish kitchen and dining area are showcased under a vaulted ceiling with wooden beams. Dark cabinetry contrasts with light countertops. A wooden dining table is surrounded by four white chairs, with a patterned rug beneath. Natural light enters through a large window, offering a serene view.
Home in Osseo
4.93 out of 5 average rating, 228 reviews

Secluded Modern Farmhouse

Escape the busy day to day hustle and come relax at this secluded stylish farmhouse located on peaceful private road and 30 acres. Spend time hiking, snowshoeing, or relaxing by the fire pit. Bring the snowmobiles, or UTV'S / ATV'S and jump on the trails. Home offers 3 bedrooms, 2 bathrooms, laundry, custom kitchen, and a 2 car attached garage. We are pet friendly and offer high speed internet.

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, 173 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