Holiday houses in Ossian

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Top-rated holiday rentals in Ossian

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

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Top Guest favourite
A rustic cabin exterior is depicted with wooden accents and a stone chimney. The porch features steps leading to a scenic view of the Mississippi River and rolling hills, framed by trees under a clear blue sky.
Cabin in Ferryville
4.99 out of 5 average rating, 106 reviews

Eagle View Lodge - 1850's Log Cabin w/ Hot Tub

In the heart of the Driftless, atop the Mississippi , enjoy the tranquility of a centuries-old Appalachian cabin. Relax on the deck & take in dramatic sunsets, soaring eagles & glistening stars. Soak in the hot tub & gaze at the majestic Mississippi. Host unforgettable dinners in the screened deck & share stories by the fireplace. Only 30 mins from Viroqua & Prairie du Chien, experience the natural beauty of the driftless region - hiking, fishing, hunting, biking - whatever inspires you.

ValueFamilyGetting around

Top Guest favourite
A rustic barn exterior is displayed, featuring weathered red wood and a metal roof. A covered porch with white rocking chairs invites relaxation, while lush green grass surrounds the structure. Tall trees provide a natural backdrop against a blue sky dotted with clouds.
Farm stay in Postville
5.0 out of 5 average rating, 117 reviews

Tranquility & Vistas on the Farm in the Guest Barn

When you arrive at our 16 acre farmstead and enter the Guest Barn, you'll notice the construction materials which were salvaged from a nearby barn and corncrib. The timbers from these buildings were torn down, moved to our farm and rebuilt into a smaller “new” barn. It truly represents a real farm experience you can feel. While here, you'll slow down and enjoy the tranquility. Walk around the farm, make friends with a cow, watch barn kitties play, while gazing across the vast farm vistas.

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Guest favourite
A restored caboose sits on a gravel base, showcasing wooden steps leading up to a porch with a railing. The evening sky displays warm sunset colors, while the surrounding landscape features open fields and sparse trees, emphasizing the tranquil rural setting.
Train in Decorah
4.85 out of 5 average rating, 507 reviews

CR Station Train Caboose

Enjoy the restoration of our charming and cozy caboose! Complete with all the amenities you'll need and more! Linens and towels, refrigerator, microwave, a double burner hot plate, dishes for cooking, barware for cocktailing, and even the original conductor's chairs to watch the sunset over the horse pasture. We also offer guided trail rides on our horses for up to 3 guests. You can book through Airbnb Experiences here: https://www.airbnb.com/experiences/6860469?viralityEntryPoint=2&s=7

ValueFamilyBackyard

Top Guest favourite
A charming Craftsman-style bungalow is presented with a wraparound porch adorned with hanging plants. Lush green grass and colorful flower beds enhance the front landscaping. The inviting entry features steps leading to the porch, and a light-colored exterior complements the neighborhood surroundings.
Bungalow in Decorah
4.96 out of 5 average rating, 202 reviews

Exceptional New Listing Decorah Craftsman Bungalow

Beautiful Decorah Craftsman Bungalow updated March 2020 that comfortably sleeps 6 in 3 large bedrooms with a king-size bed in each room. Main floor BR with en-suite bathroom and 1/2 bathroom upstairs. Beautiful hardwood floors, charm and character throughout. Large modern kitchen. Central A/C and furnace. Large porch with beautiful patio and backyard. Close to downtown and all the wonderful amenities Decorah has to offer. Quiet neighborhood and perfect for a family or couples getaway.

LocationFamilyAmenities

Guest favourite
The exterior of a two-story house is presented, featuring a red metal roof and beige siding. A welcoming front porch with steps is visible. Surrounding trees and an expansive lawn provide a sense of space, with a pathway leading away from the home.
Home in Elgin
4.95 out of 5 average rating, 120 reviews

The EJ House 4 Bedroom 1 1/2 Bath

The EJ house was built in 1905 with the original woodwork, stain glass windows and front door. The house is a little over 1600 sqft of living space. The house has 4 bedrooms with three queen beds and one full size bed. Guests will find it to be surprisingly spacious and a comfortable place to work, play or relax. There is a full-size washer and dryer in the house. The house has central air for those warm summer days or enjoy the large back deck. The woodwork is original to the house.

LocationFamilyBathroom

Top Guest favourite
A spacious living area features a comfortable seating arrangement with a television and a stylish wooden dining table that accommodates multiple guests. Natural light enters through a large window, illuminating the light-colored flooring and neutral walls.
Home in Decorah
4.94 out of 5 average rating, 110 reviews

Hillcrest Pines

Entire 3 bedroom near Trout run trail w/EV charger Peaceful 3 bedroom 2 bath home is perfect for big families or multiple families traveling together. The home is a raised ranch which features a lower level living area with a king bedroom and a pull out queen couch in the family room. Upstairs features large living room, kitchen, two bedrooms with Queen beds and queen pullout couch. The home is located less than .25 miles from the trail head for the Trout Run Trail!

LocationFamilyHiking

Top Guest favourite
A spacious outdoor area features a circular fire pit surrounded by six Adirondack chairs. The house is framed by tall trees, with large windows reflecting the natural surroundings. Steps lead to a deck above, enhancing the outdoor gathering space.
Home in Decorah
4.97 out of 5 average rating, 261 reviews

Rustic Acres Cabin & Springs

Relax and refresh at Rustic Acres Homestead & Springs. Rustic Acres was family built and is family run. This is a great place to get away and connect with family, nature, and friends. You'll get peace and quiet at Rustic Acres, but we aren't far from local attractions! We are located about two miles north of Seed Savers, three miles from Winneshiek Wildberry Winery, seven miles from Luther College, nine miles from downtown Decorah, and 13 miles from Toppling Goliath.

FamilyLocationAmenities

Top Guest favourite
A park model home is positioned on a stone terrace, surrounded by lush greenery. Large windows offer expansive views of the surrounding landscape. A wooden deck with seating is visible, extending the living space outdoors, with a tranquil atmosphere conveyed by the scenic backdrop.
Cabin in De Soto
4.96 out of 5 average rating, 161 reviews

Paradise Point sleeps 2 Hot Tub

1 bedroom 1 bath with loft. Cozy home where you can see Paradise. This memorable place is anything but ordinary. Views for miles of the Mississippi River, bluff tops and you can soar with the Eagles. What a place to relax in the newly added hot tub while you enjoy the view in what is call "God's Country". This is promised to be a one of a kind view. The Deck with comfortable outdoor seating Located in the heart of WIsconsin's Driftless Region.

ValueFamilyIndoor spaces

Guest favourite
The exterior of a two-story house is presented, featuring a sloped roof and warm wooden accents. A spacious balcony showcases ample seating and is illuminated by recessed lighting, creating a welcoming entryway. The surrounding trees hint at a serene natural setting.
Home in Decorah
4.91 out of 5 average rating, 311 reviews

Hill Top House

Located .5 miles from the Upper Iowa River, Hilltop house has the most perfect view. The house sleeps 8, but we welcome and encourage smaller groups as well. This location has 2 bathrooms, a relaxing loft and the most dreamy porch. *WARNING* When booking in the winter be aware of our driveway shown in the picture. We highly recommend 4 wheel drive. We also have a pack n play and high chair available upon request.

LocationFamilyView

Top Guest favourite
A welcoming entrance is highlighted by a decorative 'Welcome' sign and vibrant yellow flowers. The rustic log home stands in the background, featuring a covered deck with wooden railings, surrounded by greenery and gravel pathways.
Apartment in Decorah
4.99 out of 5 average rating, 341 reviews

Berry Hill Flat

Berry Hill Flat sits perched on a bluff above Trout River Valley. Trout live in beautiful places and so do we! The Flat offers a king bed in the bedroom, full bathroom, full kitchen, living room, twin bed, and private ground floor entrance. It is the lower level of our beautiful log home nestled in the walnut trees. Minutes to Decorah, Waukon, or the trout stream in the Valley below.

FamilyLocationOutdoor spaces

Top Guest favourite
A rustic cabin is set against a backdrop of lush green pastures and large trees. A herd of Icelandic sheep is seen quietly grazing, with the sun casting a warm glow over the landscape. The peaceful rural setting invites relaxation and reflection.
Guesthouse in Decorah
5.0 out of 5 average rating, 302 reviews

Acorn Cabin

Acorn Cabin sits perched on a lovely family farm just 3 minutes from downtown Decorah. The Cabin is a restored granary dating back to 1912 and has been crafted with love and attention to detail. Perfect for couples and small families. Enjoy this opportunity to stay on a working Icelandic Sheep farm with quiet, peaceful evenings, and glorious views of the surrounding countryside.

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Top Guest favourite
The kitchen features modern appliances and a spacious island with seating for several guests. Light wood cabinetry complements the kitchen's decor. A dining area with a wooden table and chairs is visible in the background, illuminated by natural light from nearby windows.
Home in Monona
4.98 out of 5 average rating, 139 reviews

Driftless Manor Getaway

The Driftless Manor Getaway is a perfect location for you and your friends or family to stay! The Driftless area has many activites such as antiquing, biking, boating, fishing, gambling, hiking, hunting, shopping, and winery/brewery hopping! Come explore the area to see what adventures you can find while staying in a roomy, relaxing space!

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Popular amenities for Ossian holiday rentals