Holiday rentals with outdoor seating in Sauk County

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.

24–31 Jan

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.

7–14 Oct

Villa in Baraboo

HUGE! 5 King, 86"TV, Playset > Dells, Devil's Lake

Welcome to Devil's Lodge! Amazing home, perfect location and unforgettable experience are all waiting for you and your group. Bring your family or friends and have a fantastic time at our beautiful home. Everyone has their seat reserved at The Table and ton of fun is waiting in the game room. For those looking for adventure, Devil's Lake, Wisconsin Dells attractions, Casino, shopping, nightlife, restaurants and ski hills are short drive away. Please contact us before booking for best pricing!

8–15 Oct

Cottage in Dane

The Napping Farm

For ten years we have welcomed travelers from all over the world to our cozy and unique farm house and we would love to host you, come as you are. If you can, please read all information provided in this listing. This is a private country house on 120 acres of woods and fields, cut in with trails, in Wisconsin's Driftless Region. Located 30 min to Devil's lake, 45 to Wisconsin Dells and only 25 Minutes to downtown Madison. Events or a party, Common Gardens for more details, we love events.

Cabin in North Freedom

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.

29 Nov – 6 Dec

Guest suite in Spring Green

Casa Natura

Located on a private 60 acres woodland and rock outcroppings. Walking paths, bluff climbing, wild edible foraging! A haven for birds and wildlife! Near the artist community of Spring Green, American Players Theater, and home to Taliesin and House on the Rock. The Wisconsin river is accessible (9 miles) for fishing,canoeing, kayaking and swimming. Great Hiking and waterfall at nearby Governor Dodge State Park. 40 miles from Madison,WI capital. We speak English, Spanish and Italian!

9–16 Oct

Cabin in Lone Rock

✧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!

13–20 Mar

Flat in Spring Green

Suite in Heart of Downtown Spring Green

Quaint apartment in historic building in downtown Spring Green. Once a 1930's grocery, building houses a one bedroom suite with full kitchen, living area with sectional, one bedroom with queen bed, one bath. All in the immediate downtown area. Free wi-fi, streaming TV. Private entry at rear of building. Sleeps two, but could sleep additional person on sectional. The apartment is downtown with a business on each side and an apartment above, so expect some noises.

15–22 Feb

Farm stay in Cazenovia

Driftless area farmhouse with silo tower

BEAUTIFULLY RESTORED CLASSIC FARMHOUSE STYLE WITH A SOPHISTICATED FLARE. NESTLED IN THE DRIFTLESS AREA, THIS HOME COMFORTABLY SLEEPS 8-10. EACH ROOM IS DESIGNED TO FLOW TOGETHER, YET HAS ITS OWN DIFFERENT STYLE. THE SILO TOWER HAS 3 LEVELS AND THE VIEW FROM THE TOP IS BREATHTAKING. ENJOY A GOOD BOOK, A GLASS OF WINE FROM ONE OF THE MANY NEARBY WINERIES, A CUP OF COFFEE OR JUST RELAX AND ENJOY THE VIEWS. THIS HOME IS DESIGNED TO ENJOY FAMILY TIME AND RELAXATION.

9–16 Sep