Family-friendly holiday rentals in Crawford County

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 (coining?:) 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. 45 minutes to Taliesin, 10 minutes to the Wisconsin River, epic bike rides out the front door.

Ohio Street Retreat- hot tub, massage chair, pool

After a fun day in The Driftless Area, come relax and unwind in Prairie du Chien. Beautifully decorated 2 bedroom home with a spacious kitchen, large island, dishwasher, washer/dryer & 5' walk in shower. We supply all cooking/baking items/utensils. High-speed internet with smart TVs in both bedrooms and living room. Outdoor pool (seasonal), hot tub and massage chair. We love dogs too, so we provide a dog run (there is a pet fee). For our fishermen- there is off street parking for your boats.

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.

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.

Hypoint Loft house-Mississippi view

Newly Constructed, (2018) Family Owned Loft House in a quiet, relaxing, 2 acre country setting overlooking the Mississippi River! 2500 sq. ft. Just 4 miles from Gatherings on the Ridge, 20 minutes from Historic Downtown Prairie Du Chien and a short jaunt to the river. Sleeps 8-10, master bedroom with a queen, 2 queens & queen sofa sleeper in loft, queen in basement , 2 baths, master bath has jetted tub, full kitchen (pots, pans, dishes, toaster, keurig, coffee pot, coffee, waffle iron, etc.)

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.

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.

Timber Ridge Cabin getaway - HOT TUB-

The Timber Ridge Hideaway is the perfect NE Iowa family retreat, with 4 bedrooms/2 bathrooms on both levels with a Bunk Bed for kids downstairs and boasting over 2200 total Sq feet. Take in the beauty of the woods and all the wildlife from the covered deck and relax in the large outdoor Hot Tub Jacuzzi available year round or the swimming pool during the warmer summer months. Just minutes away from the Mississippi River and Yellow River Forest. Sleeps up to 14.

Wrangler Outlaw Suite! Horses! Hydro-Massage Tub!

Enjoy morning coffee and sunsets on your covered deck. Cook your Cowboy Breakfast outside on the flat top griddle and grill. Come for a taste of Wisconsin's rolling green hills, bright blue skies, and fresh, crisp countryside air. Cody's Ranch is located on a ridgetop in beautiful Driftless Region of SW Wisconsin. Experience the rustic cowboy suite with a private entrance on the upper level on this lodge with a property manager on site.

Andy Mountain Cabin #3

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.

1884 Red Brick Cottage

Step back in time to a quiet small town in Iowa, nestled within the hills of the driftless area. Time seems to stand still while you're here. The 1884 Red Brick Cottage offers 3+ Bedrooms in a peaceful neighborhood, close to riverfront activities, casino and downtown Marquette. Spacious backyard and sideyard, house is fully furnished and includes a firepit and gas grill for evening outdoor activities.

3BR 2B Cabin Retreat in Beautiful Crawford County

The Cocorico Cabin is a three-bedroom, two-bath secluded cabin on over 9 acres of wooded land just 10 minutes from the Mississippi River. You'll have loads of yard space for games, or you can enjoy sitting on the deck watching birds or staring at the stars. The quarter-mile walking path through the woods leads to an outdoor bar and stage with a basketball hoop. A perfect getaway from your busy life.