Vacation rentals in Allamakee County

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Top-rated vacation rentals in Allamakee County

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Top guest favorite

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.

LocationFamilyComfort

4.99 out of 5 average rating, 114 reviews

Top guest favorite

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

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.

LocationValueWifi

5.0 out of 5 average rating, 119 reviews

Top guest favorite

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.

ValueFamilyBathroom

4.99 out of 5 average rating, 97 reviews

Top guest favorite

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

FamilyLocationDecor

4.96 out of 5 average rating, 52 reviews

Top guest favorite

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.

LocationFamilyCleanliness

5.0 out of 5 average rating, 14 reviews

Top guest favorite

A cozy living area is featured with a large sectional sofa, offering a comfortable setting near a stone fireplace. A wooden coffee table is positioned in front, while large windows provide views of the surroundings. A vibrant area rug adds a touch of color to the hardwood flooring.

Cabin in Dorchester

The Overlook Cabin

Take it easy at this high end cabin in the woods.The cabin is set in one of the most serene areas of the Northeast Iowa bluffs. You will sit on the deck and be level with the bald eagles soaring down the valley into the Bear Creek. The views from this cabin are next to none. The Cabin offers miles of hiking trails through the woods and down to Bear Creek. There are no neighbors for miles! I have two properties, The Overlook & The Barn loft, the trails connect them!

FamilyValueComfort

5.0 out of 5 average rating, 42 reviews

Top guest favorite

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

LocationValueQuiet

4.99 out of 5 average rating, 174 reviews

Top guest favorite

Cabin in Ferryville

The Sunset River View- hot tub, fireplace Romantic

Sun Set River View Cabin — Driftless Luxury With Stunning Mississippi Views Welcome to Sun Set River View, one of the most requested cabin rentals in the Driftless Region of Southwest Wisconsin. Perched high above the Mississippi River, this cozy cabin offers peaceful privacy, unforgettable views, and a relaxing retreat. Guests love watching sunsets over the bluffs from the deck or hot tub—once you experience it, you’ll see why so many return year after year.

LocationFamilyQuiet

4.94 out of 5 average rating, 126 reviews

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

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.

LocationFamilyOutdoor spaces

4.96 out of 5 average rating, 164 reviews

Top guest favorite

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.

FamilyLocationBathroom

4.99 out of 5 average rating, 216 reviews

Top guest favorite

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.

LocationFamilyNearby

4.97 out of 5 average rating, 363 reviews

Top guest favorite

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!

LocationViewOutdoor spaces

5.0 out of 5 average rating, 14 reviews