
Holiday houses in Plain
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Top-rated holiday rentals in Plain
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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.

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.

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!

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.

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!

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.

Unique Timber Frame home in Baraboo Bluffs area
5 miles from downtown Baraboo, you can follow the country roads through the Baraboo Bluffs to a majestic timber frame cabin. Tucked away on over 30 acres you'll find relaxation by the stocked pond, adventure out in the woods or cozy up by the wood burning fireplace (firewood not supplied) If you’d like to venture out , Devils lake is 15 mins, Wisconsin Dells 20 mins, and 2 ski resorts are within 25 minutes. Wineries, breweries, distillery, shops and restaurants can be found in the area.

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.

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!

✧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!

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.

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.
Popular amenities for Plain holiday rentals
Other great holiday rentals in Plain

The Yellow Farm

Brisbane House: Restored Historic Country House

Brigham View

Farm in the Driftless | Private + Family-Friendly

Family Fun Retreat w/Hot Tub & Treehouse WI.

Private Resort Cabin | Pool • Hot Tub • Sauna

The House in the Valley-Hot Tub, Sauna & Game Room

The Abbey Mansion
Destinations to explore
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- Devil's Lake State Park
- House on the Rock
- Noah's Ark Waterpark
- Wisconsin State Capitol
- Lake Kegonsa State Park
- Mirror Lake State Park
- Glacier Canyon Lodge
- Wollersheim Winery & Distillery
- University of Wisconsin
- Cascade Mountain
- Governor Dodge State Park
- Henry Vilas Zoo
- Camp Randall Stadium
- American Players Theatre
- Chazen Museum of Art
- Tyrol Basin
- Overture Center For The Arts
- Dane County Farmers' Market
- Monona Terrace Community And Convention Center
- Madison Childrens Museum
- Ho-Chunk Gaming Wisconsin Dells
- Cave Of The Mounds Lowest Point
- Buckhorn State Park
- Blue Mound State Park





