Vacation rentals in Osseo

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Top-rated vacation rentals in Osseo

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Guest favorite

Tiny home in Black River Falls

4.98 out of 5 average rating, 337 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

Nov 5 – 12

G$30,896 GYD per night

Guest favorite

Cabin in Black River Falls

4.93 out of 5 average rating, 224 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!

Apr 9 – 16

G$29,729 GYD per night

Guest favorite

Home in Chippewa Falls

4.95 out of 5 average rating, 204 reviews

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

Come stay on an extremely quiet and calm 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

Sep 11 – 18

G$43,218 GYD per night

Guest favorite

Guest suite in Strum

4.96 out of 5 average rating, 193 reviews

Private & spacious 2 bedroom suite with hot tub.

Relax at this peaceful, private suite with a hot tub. Over 800 sq. ft. of living area including 2 bedrooms with queen size beds, full bath including large shower with jets. In April 2023 we added a kitchenette with sink, fridge microwave, toaster. We don’t have a stove inside, but you have access to an outdoor gas grill. Property backs onto the Buffalo River so you can enjoy a walk along the river’s edge. Also included is the use of the fire pit, patio furniture and hot tub weather permitting.

Sep 11 – 18

G$29,935 GYD per night

Guest favorite

Apartment in Elk Mound

4.93 out of 5 average rating, 373 reviews

Oak Hill Retreat

Country location, peaceful and quiet. Apartment above detached garage, full kitchen, small deck and private stairway with beautiful view of the surrounding trees. Easily accessible, 3 miles from I-94 and St. Hwy. 29, 1/2 way between the university cities of Eau Claire and Menomonie, 1 1/4 hours from St. Paul/Minneapolis. There is a growing art and music scene, with multiple music festivals, etc. The area also has fine restaurants, theaters, parks, and historical sites. Come to be restored.

Jun 29 – Jul 4

G$17,858 GYD per night

Guest favorite

Barn in Hixton

4.88 out of 5 average rating, 231 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 as well.

Jul 2 – 9

G$27,267 GYD per night

Guest favorite

Home in Menomonie

4.97 out of 5 average rating, 109 reviews

Country home, private suite, separate entrance!

Stay in a Northern Dog Trot! Think of this place as a hotel suite but in a house in the country! Ideal for families, couples & solo travelers wanting more space. You have a separate entrance to your suite on the opposite end of our home separated by the dog trot a enclosed breezeway. We are ideally located 7 miles south of Menomonie off of Hwy 25 and 1/2 mile to quaint Downsville. The Red Cedar Bike Trail is within 1 mile. Perfect if you are visiting your son or daughter at UW-Stout.

Jul 5 – 12

G$15,836 GYD per night

Guest favorite

Guesthouse in Hixton

4.96 out of 5 average rating, 102 reviews

Country Retreat. Beautiful sunsets and sunrises.

Fresh country air. Beautiful view. Cable TV. WiFi. Hot Tub.(chemical free) Spacious furnished kitchen. Sectional sofa with recliners. Recliner. Electric fireplace. Washer and dryer. 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. Upstairs apartment is occupied but has separate entrance. We are only 25 minutes from two lakes with beaches. We are one mile from snowmobile trails.

Aug 25 – Sep 1

G$28,962 GYD per night

Guest favorite

Guest suite in Boyd

4.96 out of 5 average rating, 335 reviews

Boyd Guest Suite

1 bedroom suite situated in the lower level of a 100+ year old farmhouse. The suite is in the middle of 40 acres on a small hobby farm. Beautiful views and private location. Conveniently located 15 mins east of Country/Rock Fest grounds, 12 mins from The Barn on Stoney Hill, 30 mins from Chippewa Falls & 45 mins from Hwy 94/Eau Claire. This suite sleeps 3 adults however cots are available for up to 2 extra guests. Pets and children welcome.

Oct 16 – 23

G$11,940 GYD per night

Guest favorite

Home in Arcadia

4.95 out of 5 average rating, 134 reviews

Sonney Lodge

Perched on a hilltop in scenic Newcomb Valley, Sonney Lodge provides a quiet, country setting while still only a 10 minute drive to downtown Arcadia. Located on a dead end with a private drive and no through traffic, the lodge features 3 bedrooms, 2 bathrooms, a full kitchen, dining room and lower level entertainment room. A covered deck wraps around 2 sides of the home offering spectacular views of the surrounding hills and countryside.

Oct 3 – 10

G$35,444 GYD per night

Guest favorite

Guesthouse in Whitehall

4.96 out of 5 average rating, 119 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.

Oct 4 – 9

G$25,120 GYD per night

Guest favorite

Home in Osseo

4.93 out of 5 average rating, 141 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 60 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.

Sep 26 – Oct 3

G$38,641 GYD per night