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Vacation rentals in Highlandville

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Top-rated vacation rentals in Highlandville

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

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Top guest favorite
The cabin's exterior showcases a blue wooden facade with a metal roof, set against a backdrop of lush greenery. A stone base supports the structure, enhancing its rustic charm. In the foreground, a grassy area is complemented by a few trees, creating a peaceful outdoor environment.
Farm stay in Decorah
4.99 out of 5 average rating, 134 reviews

Footbridge Farm Cabin

Footbridge Farm is a quiet country get-away located on 90 wooded acres, 15 miles NE of Decorah. We are close to the mouth of Canoe Creek, the Upper Iowa River and adjacent to state DNR land. The cozy owner-built cabin has an open ceiling with exposed beams and rafters giving a sense of spaciousness. Local stone was used in the exterior walls and the floor-to-ceiling fire back behind the wood-burning stove. The floors are oak and slate. Detailed craftsmanship can be found throughout the cabin.

Top guest favorite
A cozy cabin is situated among lush greenery, featuring a spacious deck that extends from the entrance. The gravel driveway leads up to the cabin, surrounded by trees and wild foliage, creating a serene, natural atmosphere.
Cabin in Westby
4.99 out of 5 average rating, 125 reviews

Nature's Nest

Unwind and immerse yourself in nature at this cozy cabin overlooking Timber Coulee Creek. Large living room windows and a spacious deck provide you with a bird’s eye view of the rippling river and many types of wild life. Deer amble through the property; eagles soar and keep an eagle eye on everything. Turkeys, squirrels, coons, and myriad of birds go about their business in this serene environment. Trout fishing is an excellent pastime for those who care to cast a line. Rest, at Nature’s Nest.

Top guest favorite
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, 129 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. New workout center for all our guest to use.

Top guest favorite
The exterior of the cabin is presented, featuring a modern, blue façade complemented by large windows. A gravel path leads to a patio area with outdoor seating and a grill. Green grass surrounds the structure, enhancing its connection to the lush landscape.
Cabin in Spring Grove
4.97 out of 5 average rating, 503 reviews

Modern Country Cabin

Clear your mind at this modern, fully furnished cabin in heart of the Driftless region of MN, WI, and IA. Built in 2016, this truly unique space has everything you need for a relaxing getaway. There is plenty of space inside the cabin. The cabin contains two private rooms, one with a king size bed and the other with a queen bed. In the summer months there is also opportunity to camp, with 4 acres of luscious green space + some woodlands! Indoor fireplace, outdoor fire pit, and Traeger grill!

Top guest favorite
A cozy bedroom is presented with a spacious bed featuring a metal headboard. Natural light filters through two windows, enhancing the rustic log walls. A wooden chair is situated in the corner, adding functionality to the space.
Home in Decorah
4.98 out of 5 average rating, 166 reviews

Glenwood Getaway

1860's log cabin, remodeled into a modern house. Located 8 miles east of Decorah on 5 acres of woods. Cell service is weak (Verizon, US Cell) or not available (others). WiFi is available. TV with local BluRay/DVD/VHS only - No TV channel service. Come here to get away. The last mile to the house is a gravel road. Main entry is on the 1st (lowest) floor. One bedroom on the 2nd floor. Two bedrooms on the 3rd floor. There is one bathroom on each floor. Stairs to the 3rd floor are steep.

Guest favorite
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, 495 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

Top guest favorite
The exterior of The Barn Loft is shown during twilight, illuminated by soft lights. A sloped lawn leads to the timber-framed barn, which includes a deck and stairs. Nearby, a metallic silo is visible, adding to the rustic charm of the property.
Barn in Dorchester
4.99 out of 5 average rating, 165 reviews

The Barn Loft

The Barn Loft, located in NE Iowa, is just a short drive from some of the best trout fishing in this part of the state! It is a full Loft Space (1500 square feet) above this Timber Framed Barn built by Wally and Traci. Here you have access to your own rooms, kitchen, and more. Whether you're a large family, or a couple just trying to get away for a few days, The Barn Loft is perfect for you and your loved ones. There are miles of hiking trails and private streams. Ask about hunting.

Guest favorite
The Little Red Schoolhouse is a charming structure surrounded by lush greenery, featuring a manicured lawn and a wooden deck. A two-car garage is situated nearby, complementing the rustic aesthetic of the property. The natural surroundings include rolling hills and tree-lined vistas.
Cabin in Waukon
4.83 out of 5 average rating, 128 reviews

Little Red School House

The Little Red Schoolhouse is located in a remote and serene area of Allamakee County. It is steps away from one of Iowa’s natural trout streams Patterson Creek, the recreational playground of the Upper Iowa River, and over 1,000 acres of wild prairie and woodlands managed by the Iowa Natural Heritage Foundation. The Little Red Schoolhouse is surrounded by natural beauty and can provide a quiet refuge free from all distractions. We are excited for your stay!

Top guest favorite
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, 246 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.

Top guest favorite
The exterior of a large yellow farmhouse is visible, featuring a wraparound porch with decorative white railings. Tall trees provide shade in the foreground, while blue skies and scattered clouds enhance the inviting atmosphere of the residence.
Home in Decorah
4.94 out of 5 average rating, 112 reviews

Fjord Farmhouse—Close to Luther

Fjord Farmhouse is your perfect escape: quiet, clean, and minutes from everything. We perfectly balance peace with excitement: Explore: Minutes from Toppling Goliath Brewery, Pivo Brewing, and stunning views at Pulpit Rock. Unwind: Return to a sparkling clean, quiet home with a beautiful layout, a spacious, stocked kitchen, and a classic porch swing. 1st floor offers one bedroom & full bath access. This is the easy, unforgettable getaway your group deserves.

Guest favorite
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
4.93 out of 5 average rating, 280 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.

Top guest favorite
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, 316 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.

Popular amenities for Highlandville vacation rentals

  1. Airbnb
  2. United States
  3. Iowa
  4. Winneshiek County
  5. Highlandville