Holiday houses in Allamakee County

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Top-rated holiday rentals in Allamakee County

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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

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.

ValueLocationAccuracy

4.99 out of 5 average rating, 117 reviews

Top Guest favourite

The three-level home exhibits a blend of rustic charm and modern design. A spacious wrap-around deck extends from the main entrance, with large windows complementing the green hillside scenery. A well-maintained lawn enhances the inviting facade, anchored by a tall evergreen near the driveway.

Home in Lansing

Big River Retreat

Perfect destination for quiet get away or a family/friends reunion with direct view of Mississippi River. Peaceful, rustic, 3 level home with plenty of space with 5 bedrooms, 3.5 baths, vaulted ceiling great room with spectacular beams creating perfect gathering space for guests. Gas fireplace & coffee bar add to charm. Full kitchen & laundry. Enjoy outdoors with full wrap around deck & walk out patio & firepit in back. Lg drive thru garage allows ease of pulling boat. 5 min drive to town.

ValueLocationIndoor spaces

4.99 out of 5 average rating, 97 reviews

Top Guest favourite

Cabin in Ferryville

Aspenshire Cabin: A Nod to English Charm

Aspenshire Cabin is nestled in a valley overlooking a private stream. The Driftless Region is known for its rolling hills and beautiful landscapes. This newly remodeled cabin stands in striking contrast to the woods surrounding it. Inspired by the cozy + sophisticated vibes of Old English Charm, a nod to this design style is evident throughout. Guests are welcomed into a space curated for rest and relaxation, whether through a quiet retreat for the arts or a getaway with family and friends.

LocationFamilyQuiet

4.99 out of 5 average rating, 115 reviews

Top Guest favourite

The modern farmhouse is set against a backdrop of rolling hills, featuring large windows and a welcoming entryway. A spacious, grassy area surrounds the home, providing a peaceful outdoor setting. The exterior combines light-colored siding with dark accents, contributing to its contemporary style.

Home in Lansing

Village Creek Retreat – Modern Farmhouse in Woods

Escape to the DRIFTLESS and VILLAGE CREEK AREA at our newly renovated modern farmhouse, tucked away in the woods. This stylish and comfortable retreat is perfect for relaxing with family and friends. Enjoy the beauty of nature with complete privacy, while still being close to everything: 2-5 minutes from Village Creek Bible Camp 10–15 minutes to Lansing for riverfront fun, shops, and dining 15–20 minutes to Waukon for local conveniences, shops, and dining 35-45 minutes to Decorah

FamilyLocationAmenities

4.96 out of 5 average rating, 53 reviews

Top Guest favourite

Cabin in De Soto

Summit View Cabin In The Woods

Enjoy the Summit View Cabin In The Woods. Located in the heart of the Driftless area. Centrally located between La Crosse ,WI-Prairie du Chien,WI-Viroqua WI and Lansing,Iowa. If you enjoy hunting, hiking , fishing , being on the river then this cabin will be close to all activities. Enjoy the hot tub in the fully screened in porch, have a fire in the smoke-less fire pit. Take an educational nature walk with a 15 tree ID species walk. Plenty of parking for boats/trailers.

FamilyLocationCleanliness

5.0 out of 5 average rating, 17 reviews

Top Guest favourite

The house is situated on a gently sloping hill, surrounded by colorful flower gardens and lush greenery. A bright blue sky adds to the peaceful setting, while a wide deck is visible, offering access to outdoor relaxation.

Home in Waterville

Chimney Rock Retreat

Beautiful, Peaceful Setting to get away and unwind. Quiet and Private for a Couples Retreat, Weekend Getaway, or Family Gathering. The House is nestled among the trees, up on a lovely hill. Scenic views and walking trails through the woods. Relaxing and Private. Campfire Pit for fun outdoors on chilly evenings. Nightly Price Listed for 1-6 Guests; Groups of 7 or 8 will have additional fees. Only Registered Guests are allowed on the Property during your stay

ValueLocationCleanliness

4.99 out of 5 average rating, 175 reviews

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

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.

LocationFamilyAir conditioning

4.96 out of 5 average rating, 166 reviews

Guest favourite

A spacious blue house is surrounded by lush green grass and dandelions, set against a backdrop of rolling hills. The architecture features multiple sections with large windows, providing ample natural light and views of the landscape.

Home in Lansing

9 Bed Rooms, 2 Cabins, 18 hole disc golf course+

Very unique property located near the Mississippi River on 350 acres. Big house with 9 bedrooms and 7 bathrooms. 9 queen beds, 7 single beds, 5 sofa sleepers 2 cabins for an additional charge. Each cabin has 2 queen beds Game room with kitchenette and big screen TV Pool table and Ping-Pong table foosball table Many yard games Hiking trails 18 hole Frisbee disc golf course Amish Cabin #1 ($50/night) Amish Cabin #2 ($50/night)

FamilyLocationParking

4.88 out of 5 average rating, 60 reviews

Top Guest favourite

The exterior of the remodeled barn features a dark wooden facade with a metal roof. A spacious deck wraps around the entrance, accompanied by a fire pit area on the gravel ground. A flag is displayed, and trees are visible in the background.

Cabin in Dorchester

The Balsam Barn

Escape to The Balsam Barn, a beautifully remodeled barn tucked among the trees in northeast Iowa. The property also includes a separate, finished barn bar—perfect for gathering, playing games, or relaxing after a day outdoors. Located just minutes from trout streams and the scenic Upper Iowa River, it’s an ideal getaway for families and groups looking for a peaceful setting with plenty of room to spread out

FamilyLocationView

4.99 out of 5 average rating, 94 reviews

Top Guest favourite

A cozy sitting area features a comfortable blue sofa with decorative cushions paired with a recliner chair. A coffee table stands in front, set atop a soft area rug. The exposed stone walls and wooden accents provide a rustic charm.

Condo in Lansing

Upper Unit on N.Second St.

The Stone Home on N 2nd Street is a historic limestone building. We are 1/2 block from the Mississippi River with views of both the river and BlackHawk bridge. Across the street is the local ice cream shop. We are 1 block from main street and easy walking to restaurants/bars and shops. This is the upper level unit. There is a main level unit below this one. Stairs are required to gain access to this unit.

FamilyValueSleep quality

4.99 out of 5 average rating, 216 reviews

Top Guest favourite

A contemporary cabin is set on a lush green lawn, featuring a spacious front porch with a wooden railing. Large windows allow natural light to flood the interior, while trees and open space create a peaceful country setting.

Cabin in Harpers Ferry

Yellow River Getaway

2 Bedroom cabin with Queen Beds and Queen Sofa sleeper with comfortable mattress if you want to pitch a tent in the yard feel free. Large open living area. with firepit. 170 acres of private property with cell phone service. Nestled in the country on a dead end road. One mile from trout fishing, hunting, hiking, horseback riding and 8500 acres of Yellow River State Forest.

LocationFamilyAccuracy

4.97 out of 5 average rating, 363 reviews

Top Guest favourite

Cabin in De Soto

August Ridge / HOT TUB / Sleeps 4

Welcome to August Ridge, a thoughtfully designed blufftop retreat where modern comfort meets unforgettable views. Perched high above the Mississippi River Valley, this two-bedroom, 1.5-bath getaway offers the perfect place to relax, reconnect, and soak in the beauty of Wisconsin’s Driftless Region. Hosted by Rentals Justin Time Hot tub is available year round!

LocationConditionAccuracy

5.0 out of 5 average rating, 15 reviews