Vacation rentals in Plain

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Top-rated vacation rentals in Plain

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Top guest favorite

A rustic cabin is surrounded by lush greenery, showcasing a spacious front porch with multiple wooden chairs and a swing. An outdoor fire pit is surrounded by seating, creating an inviting space for gatherings. A shaded gazebo adds to the outdoor comforts.

Cabin in Hill Point

Big R's Retreat Secluded and located in Nature

Welcome to our home: where we have found peace and relaxation for over 20 years. A German native, Big R fell in love with the open land and rolling hills of Wisconsin, becoming a US citizen in the 80s. He met Curly, a Chicago city girl, who brought a little city to his country life. They enjoy raising buffalo and spending warmer days on their porch enjoying the fresh air and beautiful views (with no mosquitos!). Now they want to share their idyllic and peaceful home with you. Drive down a dead-end road and pull up to a rustic cabin filled with high-tech and cozy amenities. We have something for everyone with a gas fireplace, tv (complete with dish, Cinemax, HBO and a Bluetooth sound system), board games and a full kitchen. Take a drink outside to soak in the hot tub or sit around the campfire. When the day is done, you will fall asleep instantly on the memory foam bed, either in the loft or the bedroom, and wake up to a beautiful sunrise looking out over your little getaway.

4.97 out of 5 average rating, 632 reviews

Top guest favorite

A well-maintained home exterior is surrounded by a lush garden, featuring a variety of plants and shrubs. The entrance is framed by a decorative archway, and a large tree provides shade. An inviting walkway leads up to the front door, enhancing the overall charm of the property.

Guest suite in Spring Green

Spring Green River Pines

Spend a few days in the beautiful countryside. A private entrance to the lower level of home (completely separate from our home) that includes a central room, 2 bedrooms with kitchenette, & 1 lg bath. WiFi >500 Mbps speed. Smart 60" TV, Bluetooth Airplay/stream compatible. Parking on sight. Great location 5 min from beautiful downtown Spring Green. Close to APT, Taliesin/Frank Lloyd Wrights Home/School, House on the Rock, WI River, Gov. Dodge State Park and 1/2 hr to Devils Lake State Park.

4.92 out of 5 average rating, 194 reviews

Top guest favorite

A cozy cabin is perched on large boulders, surrounded by lush greenery. It features a spacious deck with railing and multiple seating areas, offering a serene view of the wooded area. The stone chimney adds character to the rustic design of the cabin.

Cabin in Avoca

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.

5.0 out of 5 average rating, 247 reviews

Top guest favorite

A charming red cabin is nestled among lush greenery, showcasing large windows that invite natural light. A white porch with comfortable seating overlooks the well-maintained yard. A red barn is visible in the background, surrounded by grass and trees.

Farm stay in Plain

Grateful Farms Cabin: Hills, Creek, Gorgeous Views

Fully-renovated 1890s cabin located on a 60+ acre farm just north of Spring Green. The cabin has heat, is air conditioned, has a small kitchenette, bathroom with shower, and wireless high-speed internet. The farm has a barn from 1895, a main home built in 1923, apple trees, hiking trails, creek with a swimming hole, and a large hill with marvelous views. Make this your private weekend cabin or a longer-term retreat. Farm powered primarily by a large solar array atop one of the barns.

4.95 out of 5 average rating, 251 reviews

Top guest favorite

A spacious bedroom features a peaked wooden ceiling and is illuminated by natural light from two windows. A cozy striped blanket covers the bed. A nightstand with a lamp and a seating area with a chair and a sofa bed are also present.

Home in Dodgeville

Two Private Floors in Secluded Home

Exclusive use of top 2 floors of home in a scenic location. Host will reside solely in basement apartment during your stay. Location is perfect as a base for exploration. 5 minutes from Governor Dodge State Park. 8 minutes to The House On The Rock. Also close to Taliesin, American Players Theater, Spring Green and Mineral Point. Or, you can just get away from it all by enjoying this scenic location at the end of a long private driveway. If you enjoy solitude, this is the place for you!

4.99 out of 5 average rating, 103 reviews

Top guest favorite

A cozy guest suite is bathed in warm, natural light from large windows. A wooden bed is adorned with layered blankets, complemented by floral curtains. A wooden dresser and bookshelf, filled with books, complete the space, enhancing a comfortable atmosphere.

Earthen home in Spring Green

Forest Retreat in Earth Home 10 Min from APT

Welcome to the guest suite of our energy-efficient earth home surrounded by forest and hills of the gorgeous Driftless region. Enjoy access to trails across 45 acres of private woods, with a trailhead outside your door. Observe dozens of species of birds outside your window while sipping coffee from bed. Our guest suite offers the wonder of a nature-escape while remaining only a 5-minute drive from downtown Spring Green, and 12 minutes from both American Players Theatre and Taliesin.

4.97 out of 5 average rating, 107 reviews

Top guest favorite

A seating area is furnished with two modern, rounded armchairs in warm tones. A bed with an abstract headboard is visible in the background, complemented by artistic wall decorations. A large mirror reflects the space, highlighting the wooden ceiling and textured walls.

Apartment in Spring Green

TB2 Apartment

Welcome to TB2, a beautifully updated two-bedroom apartment located on the lower level of the Steampunk Manor B & B. While housed in the same building, this apartment is completely separate from the bed and breakfast, offering guests privacy, comfort, and a space all their own—including a private entrance. Throughout the apartment, vibrant colors, unique artwork, and creative details complement the spacious open-concept living and stylish bedrooms designed for comfort and relaxation.

4.92 out of 5 average rating, 292 reviews

Guest favorite

Cabin in Merrimac

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

4.92 out of 5 average rating, 283 reviews

Top guest favorite

The exterior of the cottage-style home features a brick facade with a stone chimney and green accents. Well-maintained landscaping includes a manicured lawn and shrubs, while the front path leads to a welcoming entrance. A clear blue sky provides a bright backdrop.

Home in Loganville

Hido House - cottage, 1 block from eateries

Enjoy a small village's most iconic home only about 30 minutes from Wisconsin Dells, Baraboo and Spring Green. This cottage-style home was built in the 1920s, and within walking distance to a few delicious eateries & bars. Visit Wis. Dells waterparks, Circus World (Baraboo), Devil's Lake State Park (Baraboo), House on the Rock (Spring Green), American Players Theater (Spring Green), Amish country (Loganville/Hillpoint), and more! We're also licensed & insured.

4.96 out of 5 average rating, 337 reviews

Guest favorite

The historic two-story house features a dark green exterior with white trim. A welcoming porch with wooden seating is visible on the left, while multiple large windows allow natural light to enter. A distinct gabled roof and a sloped yard contribute to the home's charm.

Home in Spring Green

Driftless Retreat in Spring Green’s downtown!

Our 4 bedroom, 2 bath home in downtown Spring Green boasts old charm and spacious room to unwind and relax throughout your stay. Home to Frank Lloyd Wright’s Taliesin, American Players Theater, the House on the Rock, and Tower Hill State Park, the vibrant village of Spring Green is a place where nature and art meet. Just 45 minutes from Madison, our quiet village boasts endless recreational and creative opportunities in Wisconsin’s beautiful driftless region.

4.71 out of 5 average rating, 106 reviews

Top guest favorite

A serene view of the Wisconsin River is captured, reflecting soft hues of sunset in the calm water. Lush greenery lines the riverbank, creating a natural frame. Gentle ripples adorn the water's surface, enhancing the tranquility of the landscape.

Cottage in Muscoda

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.

4.95 out of 5 average rating, 221 reviews

Top guest favorite

An outdoor fire pit area is surrounded by gravel, with four chairs positioned around the center. A cozy farmhouse is visible in the background, framed by lush green trees. Tiki torches are placed nearby, enhancing the inviting outdoor setting.

Farm stay in Hill Point

Ridgetop Retreat

Enjoy the natural beauty of the Driftless Area in Richland County Wisconsin. This is a well-appointed, four season country farmhouse on a fully operational farm. The access to the Richland County snowmobile trails is less than 5 miles away. Goats and chickens are out your front door. Deer, turkey, and other wildlife are in abundance. All county and township roads are open to UTV traffic. Enjoy tranquil star-filled skies all year long!

4.98 out of 5 average rating, 131 reviews