Vacation rentals in Boscobel

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.

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.

Sunrise Haven Country Cabin with a view

From our family to yours - welcome to Sunrise Haven, a rustic log cabin nestled high in the Driftless hills of Southwest WI that overlooks farmland, a Class I trout steam and woodland. We invite you to enjoy the peace, connection to nature and outdoor adventure that we truly treasure. Hiking in the woods, watching wildlife and stargazing by the campfire await. While remote, we are still just a short drive to many of our area's greatest attractions that make SW WI a great place to visit.

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.

Crooked Creek - Relaxation Cabin

Welcome to Crooked Creek – Your Peaceful Relaxation Cabin 🌿 Looking for a quiet place to unplug and breathe again? This quaint and cozy cabin sits in a serene valley bordered by tree-lined bluffs and a gentle creek—a favorite among guests seeking rest, reflection, and simplicity. Whether you're curled up by the gas fireplace, grilling dinner outside, or stargazing by your private fire pit, this cabin offers peace and privacy without distractions — exactly as described by our guests.

Wildwood Retreat

This 3-bedroom house is perfect for your escape to Boscobel. With 1 queen bed, 2 bunk bed with a queen on the bottom and a full on the top bunk, this tranquil retreat offers a soothing atmosphere for guests. Enjoy the convenience of amenities like a washing machine and dryer, WiFi, and heating. The 2 bathrooms are equipped with a shower and hair dryer. Experience the magic of Boscobel at our house. Enjoy the sunsets overlooking the field bordering the back of the house.

Hilltop Hideaway, Cabin in the Driftless Area

*New* Wi-Fi Available - 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.

The Driftless A-Frame - pet friendly

A cozy cabin within 8 acres, Muscoda, Wisconsin Step into the magic of the Driftless region at this iconic A-frame cabin. Shaped like a tent, enjoy much of what camping has to offer with the amenities of: comfy bed, linens, paper products, hot showers and cold beverages; the perfect blend of rustic charm and modern comfort. Whether you're sipping morning coffee on the deck or roasting marshmallows under a sky full of stars, you'll feel a world away from it all.

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.

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.

Upstairs Mainstreet Apartment

Bring the whole family to this great place with lots of room for fun. Walking distance to downtown Fennimore which includes restaurants, bars and shopping. This 3 bedroom 1 bath upstairs apartment has an open floor concept. This is a perfect spot for anyone wanting to stay in the Driftless Area.