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
An inviting living area features a cozy couch facing a wood-burning stove encased in local stone. Warm light from nearby lamps creates a comfortable ambiance. Exposed wooden beams are visible in the ceiling, and a soft rug adds a touch of warmth to the oak floor.
Farm stay in Decorah
4.99 out of 5 average rating, 137 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
An open kitchen area features a large island with seating for six, surrounded by wooden cabinetry and stainless steel appliances. Natural light fills the space, highlighting the bamboo flooring and creating an inviting atmosphere for meal preparation and gatherings.
Home in Decorah
4.99 out of 5 average rating, 168 reviews

The Loft

Situated just 2 minutes north of Decorah on Hwy 52, this completely separate 1,300 sq. ft space features a full kitchen, 2 large bedrooms, 1 bath, 3 queen beds & sleeps 6 people! This space has a large 6 person island to enjoy dinner &/or drinks with family & friends, or take it outside to the elevated deck & enjoy the scenery. We are just 2 minutes from the Trout Run Trail, the Upper Iowa River & Luther College, which is just down the hill. Our lovely downtown Decorah is only 5 minutes away.

Top guest favorite
Cabin in Spring Grove
4.97 out of 5 average rating, 512 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 three-story log cabin blends modern features with rustic charm, surrounded by trees. The spacious patio includes multiple seating areas with a stone path leading to the entrance, while natural greenery offers a serene backdrop.
Home in Decorah
4.98 out of 5 average rating, 167 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
Barn in Dorchester
4.99 out of 5 average rating, 166 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.

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, 250 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 interior of the silo guesthouse features a circular design with wooden beams overhead. A cozy seating area includes a large sectional sofa and a stylish ottoman. Natural light enters through multiple windows, enhancing the space, while a staircase leads to a loft area.
Farm stay in Caledonia
4.99 out of 5 average rating, 111 reviews

Silo Loft Guesthouse

Our silo guesthouse provides a beautiful country retreat surrounded by hundreds of acres of woods and farm land. This working dairy farm is the perfect stay for a tranquil get away or the full dairy farm experience. If you’re looking for a CLEAN, peaceful & unique stay, this is the place for you! Recent guests say it’s the “hidden gem” of MN! Just 10-30 minutes from local coffee shops, restaurants, and many outdoor activities, this getaway has something for everyone!

Top guest favorite
The treehouse is positioned among tall trees, with a warm glow emanating from its windows. A stone path meanders toward the entrance, surrounded by fallen leaves, while wooden steps lead up to the deck. The sky features soft hues of sunset in the background.
Treehouse in Mabel
4.99 out of 5 average rating, 186 reviews

Nestling Pines Treehouse

Nestling Pines Treehouse is nestled amongst the Pine trees on a hill deep in the woods. There is designated parking for treehouse guest only. A 60 foot bridge starts your walk up the trail to the treehouse. Then a 250 foot gravel path leads you to this beautiful Treehouse. Has electricity, running hot/cold water, walk-in-shower, flushing toilet, 2 full size beds, fridge ,A/C, electric heat , ample kitchen amenities, toiletry items supplied, and housekeeping.

Top guest favorite
Home in Decorah
4.93 out of 5 average rating, 113 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.

Top guest favorite
A hot tub is positioned on a wooden deck, offering panoramic views of the Mississippi River below. Trees frame the scene, with the sun illuminating the cloudy sky while water bubbles invitingly in the tub.
Cabin in De Soto
4.96 out of 5 average rating, 137 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.

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
4.92 out of 5 average rating, 286 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.

Popular amenities for Highlandville vacation rentals

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