Holiday houses 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, 462 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
The cozy living area features two inviting sofas and a wooden coffee table, surrounded by warm wood paneling. A flat-screen TV is mounted above a stone fireplace. Natural light floods in through expansive windows leading to the sunroom, where comfortable seating offers views of the lake.
Cabin in Lake City
4.92 out of 5 average rating, 105 reviews

Perched Above Pepin-cozy cabin,panoramic lake view

Charming cabin perched on a hill w/ stunning views of Lake Pepin.Enjoy a cozy atmosphere w/ a fireplace, modern amenities, & sunroom w/ breathtaking lake vistas. Watch eagles soar and barges pass by, while listening to the sound of trains rolling by along the river.Located near hiking trails, water activities, local wineries, and breweries, this cabin is perfect for outdoor adventures.With easy access to both Lake City and Wabasha, it’s an ideal getaway, blending comfort, nature, and attractions

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!

Guest favourite
A living area features a cozy seating arrangement with a sofa and an accent table. Adjacent, a dining table with four chairs is complemented by a kitchen bar with three stools. Natural light enters through large windows, enhancing the open and inviting space.
Bungalow in Chippewa Falls
4.85 out of 5 average rating, 274 reviews

The perfect north woods getaway on Lake Wissota!

Stand-alone home retreat on the lake! Quiet, stylish, lakefront cabin located on Little Lake Wissota. Easy access off of Hwy X, restaurants, grocery store, & Ray's Beach all within walking distance. This 800-sq-ft home w/ beautiful lake views, 2 bedrooms, with queen-sized beds and a pull-out full sofa/sleeper. Outdoor features include a paved patio, patio table & chairs, bonfire pit, charcoal grill, waterfront & private dock. Chippewa County zoning permit # 09-2017-ZON-0185 Book it today!

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, 315 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 view of the Mississippi River is seen from the apartment, with lush green bluffs in the background. Nearby buildings exhibit charming architecture, and parked cars line the streets. A light post adorned with an American flag stands in the foreground.
Apartment in Trempealeau
4.98 out of 5 average rating, 141 reviews

Small Town Vibes with Amazing River & Bluff Views

Enjoy gorgeous view of the Mississippi River, bluffs, and trains, entertain yourself with the live music (occasionally late) from neighboring establishments, stargaze on the deck, or revel in the passing trains. This apartment is the perfect place to get away and relax. Bring up your boat as you'll have parking available in the driveway too! NOTE: this is an upstairs apartment, but we promise you won't be disappointed and want to come back again and again. NON SMOKING. No pets.

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.
Guesthouse 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, 143 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
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 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.
Guesthouse in Whitehall
4.96 out of 5 average rating, 147 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.

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