Holiday houses in Crawford County

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Top-rated holiday rentals in Crawford County

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

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Top Guest favourite
A secluded off-grid bunkhouse is nestled among lush greenery, framed by a vibrant sky. The rustic cabin features a welcoming porch and large windows, providing a serene view of the surrounding restored prairie and mixed forest.
Guesthouse in Gays Mills
5 out of 5 average rating, 94 reviews

The Bunkhouse on 80 acres, trails

Relax with the whole family in our secluded OFF GRID Bunkhouse. Hike trails, immerse in nature, discover wildlife. 80 acres. Or head into town for Americana, quaint farms, local flavor. Tour Wisconsin's Driftless area. One bedroom with queen bed One bedroom with twin bunk beds One full sized futon in living room. Wood burning stove. THIS CABIN IS OFF GRID. NO RUNNING WATER, NO ELECTRICITY. BATHROOM HAS SAWDUST TOILET and TUB, but heat water on the stove for bath. Old fashioned, slow-living.

Top Guest favourite
A charming farmhouse is nestled among lush greenery, surrounded by tall trees. The two-story structure features a gabled roof and a covered front porch. Natural landscaping, including shrubs and grass, frames the house, creating a serene and private atmosphere amidst the forested hills.
Cabin in Gays Mills
4.98 out of 5 average rating, 381 reviews

Driftless Region Cabin/ Stream and Sauna

Settle into a quaint farmhouse nestled in a valley in the rolling, forested hills of the Driftless Region. Start your day with a cup of local coffee on the front porch. Go on a long walk or bike ride, then return to the cottage to cook, play board games, listen the record collection or visit Viroqua (25 minutes) for a farm-to-table 5-star dinner, or check out local music. Build a warm fire outdoors/ warm up by the gas stove indoors, or go down to the stream for a sauna by the cool water creek.

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
4.99 out of 5 average rating, 93 reviews

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.

Top Guest favourite
A serene view of the Mighty Mississippi River is captured during sunset. Soft hues of orange and purple fill the sky, while the landscape is framed by lush green trees and gentle mists rising from the water, creating a tranquil atmosphere.
Home in Lynxville
4.86 out of 5 average rating, 277 reviews

Highland Hideaway

A cozy, secluded two bedroom cabin located in the driftless region with incredible views of the Mighty Mississippi!!! If you’re looking for peace & quiet, beautiful sunsets, watching wildlife or barges cruise this is your place. Only 20 minutes from Wyalusing or pikes peak state park, The Effigy Mounds (Indian Burial Grounds)and Historic Villa Louis. This beautiful cabin centers you 30 miles from amazing hiking, fishing, hunting and nature for a weekend of disconnecting from busy life.

Top Guest favourite
The A-frame cabin is surrounded by tall pine trees, showcasing a red exterior with large windows. A spacious porch, furnished with chairs, extends across the front, inviting relaxation in the natural setting. The lawn is lush and well-maintained, enhancing the cabin's serene atmosphere.
Cabin in Steuben
4.97 out of 5 average rating, 65 reviews

Peaceful Driftless A-Frame

Nestled among two acres in the rolling hills and lush greenery of the Driftless Area, this A-frame cabin stands as a serene retreat, blending harmoniously with its natural surroundings. The decor is a blend of modern comforts and rustic elements, with comfortable furnishings. Seated in the heart of the Kickapoo valley, there's no shortage of class 1 trout streams near by, public hunting easements, UTV trails, hiking, canoeing and easy access to all of the wonderful amenities the area offers.

Superhost
A single-story farmhouse is set against a backdrop of greenery, showcasing a combination of stone and wooden exterior. The well-maintained lawn is complemented by surrounding trees, with a pathway leading towards the entrance. A spacious deck is visible to the side, enhancing the outdoor appeal.
Farm stay in Wauzeka
4.81 out of 5 average rating, 317 reviews

Larsen Farm Secluded Farmhouse with Hotub

Secluded farmhouse with glass hot tub room 600 acres of private trails to hike and explore the cave. Bring your UTV and ride the trails for $30 per driver and $10 per passenger or rent a UTV for $300. Close to trout fishing stream or Mississippi for fishing. Approx 15 miles from Prairie Du Chein, close to canoeing for the Kickapoo, Wisconsin river. Has a gas & charcoal grill, pool table, firepit, Smart TV. Private trails closed Oct 15th thru mid Feb There is Access to public UTV trails.

Top Guest favourite
The cozy cabin features a log exterior with a welcoming deck surrounded by nature. The structure is set on a slight incline, decorated with stone landscaping and a few pumpkins. Trees frame the background, contributing to the serene atmosphere.
Cabin in Boscobel
4.95 out of 5 average rating, 136 reviews

Cozy creekside Driftless Log Cabin on beaver pond!

Peeping frogs, singing birds, rustling trees, hooting owls, gurgling creek, howling coyotes: these sounds will surround you during a week here! Cabin is cozy, with an aesthetic we're calling supper-club-chic. The perfect place to read, relax, reconnect. Nestled in the heart of Wisconsin's Driftless area, a remote, lovely, nearly-wild kingdom, easy driving distance from Chicago and Madison. As of 2025, a resident beaver family are redesigning the creek/yard: you'll have a front row seat.

Top Guest favourite
The cabin's exterior is showcased against a backdrop of lush trees. A sloped metal roof complements the wooden siding. A welcoming entry is framed by a set of stairs leading to the front porch. Gravel surfaces surround the cabin, enhancing its secluded feel.
Cabin in Eastman
5 out of 5 average rating, 112 reviews

SereniTree Cabin-Modern Rustic Getaway

Modern Rustic Family Getaway- Our cabin is not a place to stay while on vacation...our cabin is the vacation! You can come and enjoy the surrounding areas if you want, but you can also just come and spend the entire time away from the outside world. It is a quiet, peaceful, relaxing place to just unwind. Located up on a bluff, between Prairie Du Chien and Ferryville, this cabin gets you about 5 minutes from the river but allows you the serenity of being tucked away in the trees.

Top Guest favourite
Home in Wauzeka
4.94 out of 5 average rating, 17 reviews

Plum Creek Cabin: Nature Lover’s Retreat +HOT TUB

Relax at a charming cabin nestled on a farm in the heart of Plum Creek Valley, offering picturesque views and a class 1 trout stream on property. This idyllic getaway is a mix of woods and pasture, perfect for immersing yourself in the beauty of nature. Access to nearby UTV/snowmobile trails. Whether you’re here for outdoor activities or simply to unwind in a serene setting, this cabin is an ideal retreat for families, friends and outdoor enthusiasts.

Top Guest favourite
A spacious living area is highlighted by natural wood beams and a high ceiling. Two comfortable seating areas, featuring a dark sofa and two red chairs, surround a round coffee table. Large windows provide ample natural light, offering views of the surrounding landscape.
Farm stay in Gays Mills
4.96 out of 5 average rating, 77 reviews

Kickapoo River Farmhouse

Come and unplug at a farmhouse on the Kickapoo river! Enjoy the driftless beauty of rolling hills, river views and wildlife from the back porch. Bring your whole family- the house sleeps 5-6 comfortably, has a full kitchen, dining room, living room and plenty of reading nooks to cozy up to a good book. Enjoy listening to records, playing board games, puzzles, yard games, lounging by a campfire, along with everything the driftless region has to offer.

Guest favourite
The exterior of a log cabin is shown, featuring a warm wooden facade and a peaked roof. A large window allows natural light to enter, while a porch is visible, framed by a rustic wooden beam. Surrounding greenery complements the natural setting.
Cabin in Harpers Ferry
4.83 out of 5 average rating, 201 reviews

Andy Mountain Cabin #4

Whether you are….. Camping, Gathering with family or friends, Hunting the Yellow River State Forest, Fishing and Boating on the Mississippi River or Snowmobiling ……Andy Mountain Cabins is the perfect Home Base for intimate or large groups. Andy Mountain Cabins, LLC is the prime log cabin choice for lodging or motels in Northeast Iowa, Allamakee County, Harpers Ferry Ia, Prairie du Chien WI, or McGregor Iowa.

Top Guest favourite
The exterior of a stone cottage is presented, featuring a front porch with a wooden overhang supported by triangular beams. Lush greenery surrounds the entrance, complemented by colorful flower boxes and well-maintained landscaping. The warm tones of the stone create a rustic and inviting appearance.
Cottage in Woodman
5 out of 5 average rating, 124 reviews

The Cottage at Streamwalk

Located off the beaten path in a beautiful pristine valley, this 1 bed, 1 ½ bath cottage offers high end furnishings with a vintage flair modeled after a true english stone cottage. The cottage offers miles of private walking trails on 100 private acres along the renowned Big Green trout stream. Our small highland cow herd roams the pastures, making it feel like you truly are in the Scottish Highlands.

Popular amenities for Crawford County holiday rentals