Holiday houses in Boscobel

Driftless Lodge Rustic Spacious Cabin

The Driftless Lodge is located in the beautiful Driftless area of WI on our working farm. It sleeps 9 people, 3 floors with 3 full bathrooms, large loft, deck w/charcoal grill, 2200 square feet of living area. Outside the cabin you will see our American Paint Horses, goats, 2 sheep, farm cats and beef cattle. We are located a few miles from Class 1 trout streams, Wisconsin River, & direct access from property to ATV/UTV routes , public land for hiking , snowmobile trails, and much more.

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. New workout center for all our guest to use.

Century Old Charming Farmhouse Atop Rolling Hills

All Season fun! A place to get out in the fresh air, sit by the campfire, & gaze at the stars. Fish the many TROUT streams nearby. Hike, bike, and horseback trails at Ash Creek Forest. WI River-4 miles away. Wild Hills Winery - right next door! Richland Center offers a Drive-in, Pine River Trails & Kayaking, beautiful parks, aquatic center, 18 hole disc golf course, books, coffee shop. Eagle Cave is a fun,brief, tour -10 miles away. *NOTE: NO PETS, NO SMOKING! **WE ARE 1 Hour from the DELLS!

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.

Glory View Ridgetop Bungalow

Farmhouse Bungalow sits on top of a ridge in the Southwest WI driftless area, boasting spectacular views. A site that works for anyone from a relaxing retreat to a great spot for adventures. Fall photography dream, cyclists paradise, star gazing/campfire, hiking, kayaking, canoeing, fly fishing, Frank Lloyd Wright, WI Dells and other local attractions. The home was completely renovated with all the modern conveniences but the Farmhouse charm. A sleeping loft adds additional functionality.

Cool quiet country cabin on boulders and 120 acres

Funky, tidy 23 year old country cabin on 120 acres of farmland & woods in a private, quiet rural setting. It's cozy, 950 sq ft, built with stone and wood. Open concept with a two story fireplace, porch fireplace, firepit, and open loft for sleeping (1 bed), with spiral stairs, lots of windows, walnut floors and trim, oak beams and pine kitchen tops. Shower is big and open, with doors opening to a back deck for outdoor showering. Beautiful covered porch overlooking rolling meadows and woods.

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.

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.

The Driftless Escape! Modern, large cabin/57 acres

Nested in between 2 valleys is this abundant log cabin next to a stream. WI river: fishing, tubing, canoeing, water sports 10 min away. Nearby: biking, trout fishing, hiking, cross country skiing, sledding, snowmobiling, wine tasting tours, historic towns and sights. Note some photos are of the surrounding area/opportunities. The 2150 square foot home boasts a fireplace enhanced by a 2 story rock faced chimney, an expansive wrap-around porch, a master suite, and a generous great room.

✧Driftless Chalet✧ Secluded cabin on 5 acres

Welcome to Driftless Chalet! The wonders of the Driftless Area lie just outside your window. Located on 5 wooded acres just past Spring Green, make this cozy cabin (with fast wifi, heat and A/C!) your HQ as you explore American Players Theater, House on the Rock, Taliesin, state parks, the WI River, wineries and more. Watch for deer and birds while sipping coffee on the porch, roast marshmallows over the campfire, bust out the board games and make lifelong memories!

River's Edge Cabin, LLC

We welcome you to be our guest in our comfy, warm cabin nestled on the lower Wisconsin River. We are close to many area attractions including Frank Lloyd Wright's Taliesin, House on the Rock, American Players Theater, Wisconsin Dells, and much more! Activities include canoeing, fishing, hunting, shopping in quaint villages, or just relaxing watching the river... Our cabin is easy to get to and close to area villages but in a private setting.

Hilltop Hideaway, Cabin in the Driftless Area

Comfortable Amish built cabin located in the Driftless Area of Southwest Wisconsin, close to area towns but still in a private setting. We are close to many area attractions including the Wisconsin River, House on the Rock, Frank Lloyd Wright's Taliesin, The American Players Theater, Wisconsin Dells, and much more! The cabin is an ideal place to relax for both couples or families who would like to escape the city and spend some time in nature.