Vacation rentals in Readstown

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Top-rated vacation rentals in Readstown

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Top guest favorite

The cabin's exterior showcases rustic wooden walls complemented by a maroon metal roof. Flower boxes adorn the windows, and a spacious deck features seating arrangements. Lush green landscaping surrounds the cabin, enhancing the tranquil wooded setting.

Cabin in Viroqua

Squirrel Ridge Log Cabin

A cozy cabin nestled in the country side of southwest Wisconsin. Located on our 28 acre organic maple syrup farm. This Amish built log cabin has its own driveway offering privacy for a perfect getaway! Sleeps 4 adults, which includes a queen bed in the master bedroom, 2 single beds in a loft area, & a queen size pullout sleeper in the main room. Ideal location in the Driftless Area for excellent trout fishing. Located just 10 minutes from downtown Viroqua for convenient dining and shopping.

4.97 out of 5 average rating, 176 reviews

Guest favorite

The two-story cabin, crafted from barn tin and local woods, features large windows, including a prominent half-round window. A covered porch with a railing invites relaxation, surrounded by vibrant flowers. The structure is complemented by the natural landscape and nearby outbuildings.

Home in Viroqua

Tin Terra Cabin in Amish Paradise with Steam Sauna

Tin Terra Cabin (TTC) is part of Sittin Pretty Farm. TTC is an artful rendering of home using the character and patina of old barn tin and boards accented with the elegance of finely crafted local woods including cherry, red oak, hickory and black walnut. Once inside a feeling of marvel and serenity are sure to help in making heartfelt memories. We are six miles from the attractions of "Viroqua hip" yet nestled in the plain and slow of the Amish with roadside stands cascading produce and pie!

4.92 out of 5 average rating, 129 reviews

Top guest favorite

A rustic living room features exposed wooden beams and a combination of vintage and contemporary furnishings. A leather sofa and armchair are positioned near a wooden table. A record player sits on a weathered console, while decor items and plants add character to the space.

Cabin in Readstown

Driftless Log Cabin w/ Kickapoo Valley View

Owned by musician @loushields & the owner of a local Vintage Clothing shop Stacey Roou @driftlessartifacts, this log cabin is a unique place that has a style all its own. It was built upon a high bluff in the Town of Kickapoo with beautiful views of the Kickapoo River Valley. Enjoy spending time with family/friends at this peaceful Driftless region retreat. The cabin is situated on 15 acres w/ wooded hiking trails (ask us how to find the trail and springs)! Follow/tag us @driftlessadventures

4.93 out of 5 average rating, 76 reviews

Top guest favorite

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

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.

4.98 out of 5 average rating, 392 reviews

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.

4.99 out of 5 average rating, 103 reviews

Guest favorite

An aerial view captures the expansive landscape adorned with autumn foliage. A spacious cabin, surrounded by rich greenery and colorful trees, is situated on a grassy area. Rolling hills stretch into the distance under a warm sunset sky.

Cabin in Readstown

Driftless Dreams Cabin

Make some memories at this unique and family-friendly place. Listen to the rain on the tin roof. Sit on the furnished front porch and watch the birds. Light a fire in the indoor fireplace or roast marshmallows outdoors. Enjoy coffee on the balcony off the master bedroom. This peaceful getaway sits on seven acres with two bedrooms and a loft, it can sleep eight with a pull out couch. Just outside of Readstown, minutes from restaurants and ice cream! Shop at Amish homes nearby.

4.82 out of 5 average rating, 84 reviews

Top guest favorite

A modern living area features a dark sofa complemented by a vibrant orange chair. A decorative area rug with blue and orange patterns adds warmth. Natural light filters through three windows, illuminating the stylish decor and shelving on the wall.

Apartment in Viroqua

Bright two bedroom rental in the heart of downtown

Enjoy a comfortable experience at this centrally-located rental, just steps away from downtown Viroqua. Grab a coffee at Wonderstate Cafe before heading over to the farmers market right next door. Explore the thriving art scene and local shops, before finishing off the evening with a dinner at the Driftless Cafe. This will also make a great homebase for hiking, biking, fishing, and paddling out in the great Driftless area. We love our little town, and hope you do too!

4.94 out of 5 average rating, 200 reviews

Guest favorite

A modern cabin is seen perched on a hillside, surrounded by tall trees. The cabin features a welcoming deck overlooking a tranquil pond with clear water reflecting the natural surroundings. The landscape includes gently sloping greenery leading to the water's edge.

Cabin in Readstown

Driftless Cabin Acreage, valley stream & pond

Modern Amish built cabin secluded on a hillside. Comforts+rustic charm, nestled in a ruggedly beautiful Driftless valley 10 mi. to Viroqua. Deck & patio overlooking pond, stream and natural springs; surrounded by steep ridges. *Freezing temperatures make slick conditions possible throughout the property.* 5 queen beds +sleeper sofa & 2 full bathrooms. Basement makes for a good “suite” w/ Couch or air mattress. AC & furnace, wood stove, stocked kitchen & good WiFi.

4.9 out of 5 average rating, 239 reviews

Top guest favorite

An outdoor deck features a cedar hot tub and seating area, surrounded by natural landscapes. In the background, a fire pit is set up with chairs, while a picturesque sunset casts a warm glow over the serene surroundings.

Cabin in Viola

Secluded cabin,cedar sauna & hot tub,outdoorshower

360 views in the middle of 75 organic acres, no neighbors in site. Outdoor Cedar hot tub & infrared sauna, heated outdoor shower, two king loft bedrooms, full kitchen, back deck with custom hibachi grill to watch sunrise and front covered deck to watch sunset. Indoor/ outdoor fire places. Wildflower fields.We try to give our couples priority booking when they rent our wedding venue 2 miles down the hill (Chapters on the Horizon) that is why we do not instant book.

4.99 out of 5 average rating, 180 reviews

Top guest favorite

A cozy living area is presented with a light gray sofa and a darker gray armchair, complemented by decorative pillows. A wooden coffee table with pumpkins adds a seasonal touch. Natural light enters through sheer curtains, illuminating the rustic wood accents on the walls.

Home in Viola

Rustic River on Main

Beams and barn boards give this two bedroom cottage a rustic style all it's own. The European influence found throughout the home, helps create an atmosphere of tranquility. Throw some steaks on the grill and enjoy a glass of wine in your private courtyard. The year round hot tub is a great way to unwind at the end of your day with access to the courtyard straight from the master bedroom. Pets are welcome with an additional fee.

4.96 out of 5 average rating, 156 reviews

Top guest favorite

A cabin exterior is showcased, featuring dark wood siding and a steeply pitched roof. A spacious deck with chairs and potted plants invites relaxation. Large windows allow for natural light, and a balcony is visible above the entrance, enhancing the overall charm of the space.

Cabin in Viola

River Valley Cabin

Very private on-the-grid cabin overlooking the Kickapoo River. Kitchen & bath, dining room, one bedroom and futon in the large living room. TV and internet, laundry and cooking. Bring your own phone. Two additional cots provided. Stunning views for every season, a unique and colorful experience in nature any day of the year. The best hunting and fishing, canoeing and horse riding, nature trails, morels and foraging.

4.99 out of 5 average rating, 172 reviews

Guest favorite

The farmhouse exhibits a white exterior with a green metal roof, surrounded by a well-maintained grassy lawn. Decorative orange pumpkins and yellow mum flowers line the front, while trees provide shade and a sense of privacy.

Home in Soldiers Grove

Driftless Century Farm

Historic farmhouse with modern comfort in the scenic Ocooch Mountains. Originally a one-room log home from the 1800s, this spacious retreat offers peace, charm, and all the comforts of home. Relax in the large backyard, listen to the sounds of nature, and enjoy the quiet beauty of Wisconsin’s driftless region. Perfect for a cozy escape or outdoor adventure.

4.91 out of 5 average rating, 171 reviews