Holiday houses in Highland

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!

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 (coining?:) 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. 45 minutes to Taliesin, 10 minutes to the Wisconsin River, epic bike rides out the front door.

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 radiant floor heat, is air conditioned, has a small kitchenette, bathroom with shower, and wireless 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.

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.

Somewhere Together

Iconic A-Frame cabin nestled on 8 acres of towering pines, just one hour west of Madison. Treat yourself to a few days of total relaxation at this intimate and charming retreat. Fish, canoe or kayak on the WI river (recommendations available). 4,000 acres of DNR land across the street. Wake up for breakfast at Vickie's Cafe (a MUST), enjoy a wine tour and tasting at Wild Hills Winery, or just unplug and snuggle in at home, with lazy morning coffee on the deck & a campfire under the stars.

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!

Highland: Driftless Fun Awaits

Highland House: tiny village, big countryside! This is your base for all your Driftless adventures. Stay in one of Wisconsin’s friendliest villages, grab your morning coffee at ‘The Front Porch Cafe’ just a few steps from the house (try the pie it’s delicious!). Hike, bike, swim, or ski at the local state park, take in a tour of Taliesin or a play at American Players Theatre, and return home to your stylish ‘home away from home’, with comfy beds, great linens, and a well stocked kitchen.

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

✧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!