Holiday rentals in Highlandville

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Top-rated holiday rentals in Highlandville

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

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Guest favourite
A vibrant sunset casts shades of pink and purple over calm waters, with silhouettes of hills in the background. A group of people is gathered on a wooden dock, with a boat covered in a tarpaulin nearby. Trees frame the scene, adding to the natural beauty.
Cottage in La Crosse
4.87 out of 5 average rating, 375 reviews

Sunsets on the Edge

My place is 10 minutes from downtown La Crosse, close to the airport, but you'll feel a world away. You’ll love my place because of the peace and quiet, but mostly THE VIEWS. All the modern conveniences of dishwasher, microwave, shower and stove/fridge, washer & dryer. You'll never see the same sunset! My place is good for two people or solo adventurers.Full list of amenities available, but worth noting here that coffee is NOT provided. There is a drip coffee maker, as well as a spot for kpods.

Top guest favourite
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, 138 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 favourite
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, 513 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!

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, 497 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 favourite
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, 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.

Guest favourite
A two-story home is surrounded by a well-maintained lawn featuring green grass and flowering shrubs. The exterior showcases neutral siding and a gently sloped roof. A patio umbrella is visible near the entrance, providing shade. Towering trees create a natural backdrop.
Cottage in Decorah
4.95 out of 5 average rating, 77 reviews

Bear Creek Cottage, Decorah, Ia (Highlandville)

Nestled in Northeast Iowa's Driftless Region approximately 14 miles northeast of Decorah, you will find this fully stocked, ready to use 3 bed home. Walking distance to Bear Creek, the top stocked trout fishing stream in the area and also Highlandville General Store. Firewood is available for purchase. Covered carport parking, up to 2 cars. Cell services is very limited and WiFi can have weak rural signal from time to time - here's your opportunity to go off grid and unwind!!!

Guest favourite
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, 133 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 favourite
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, 114 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 favourite
The image shows a sandy area with a decorative bench surrounding a fire pit, positioned amid tall trees. The treehouse is visible in the background, elevated on a platform with stairs leading up from the ground.
Treehouse in Mabel
4.99 out of 5 average rating, 187 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 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, 140 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.

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.
Flat in Decorah
4.99 out of 5 average rating, 324 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.

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.
Guest house in Decorah
5 out of 5 average rating, 290 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.

Popular amenities for Highlandville holiday rentals

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