Vacation rentals in Cross Plains

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.

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Walk to Camp Randall • Entire Home Near UW

Steps to Camp Randall & an easy walk to UW–Madison! Spacious home for up to 10 guests with a comfortable layout, multiple bedrooms, full kitchen, and inviting gathering spaces. Enjoy the back patio—perfect for unwinding after a day on campus or exploring the city. Ideal for Badgers game weekends, family visits, and group stays. Please note: during football weekends, the host may use the garage and part of the driveway for tailgating; parking may be shared. Cleaning fee $150. No pets or smoking.

Black sheep cabin with barrel sauna. New build!

Discover peace and style in this brand-new cabin tucked away in the woods—just minutes from the Dells. Modern aesthetic and thoughtful details, this secluded retreat blends natural beauty with upscale comfort. Wake up to birdsong, sip coffee on the private patio, and unwind in a space that feels serene & sophisticated. Whether you're seeking a romantic getaway, a quiet workcation, or a base for Dells adventures, this peaceful woodland hideaway offers the perfect balance of privacy and proximity

Private guest suite on beautiful Lake Mendota

Cozy guest suite/basement apartment with separate entrance for nature lovers. Lake and capitol views from breakfast nook with microwave and mini fridge and coffeemaker. Full kitchen coming fall 2025. Quiet, woodsy, neighborhood adjacent to Governor Nelson State Park. Completely painted and updated 7/25/24. Tiki level, pier, and kayaks for guest use. People love the views, the hot tub and woods. It is a 1929 cabin so many stairs, some indoor insects and limited space. Well behaved pets welcome!

Cottage Suite + Jacuzzi Bathtub & Sauna

This Suite is perfect for 1-5 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond/Bodywash

Sauna | Hot Tub | EV+ | Luxury | Cozy | Private

Nestled in the country, this luxurious home offers a serene escape from the hustle of city life. Enjoy two spacious bedrooms and two meticulously designed bathrooms featuring indulgent amenities, such as a deep soaking tub. A cozy living area with a stone fireplace invites relaxation, while a gourmet kitchen beckons culinary adventures. Outside, soak in the hot tub, grill up some dinner, share stories around the fire, or watch the sunset from the sauna, all amidst nature's embrace.

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

Charming Milkhouse Cottage, minutes from Madison!

Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!

Campo di Bella Winery & Family Farm LLC

Welcome to Campo di Bella Farmstay. We have created a private retreat above our winehouse on our farm. You will enjoy the sights and sounds of country living. Weekend Farm to Table dinners available on-site and we typically reserve seating for our farmstay guests. From December to end of March, we are only offering dinners on Friday nights. Max room rate $175.00. Please note that during winter months, we are on a private road and snowplowing may be completed by early afternoon.

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!

Real Christmas Tree Farm! Skiing nearby

Get lost in nature and stay where the magic grows on a real Christmas tree farm! Situated on rolling hills below the Baraboo bluffs, this 125 acre farm and nature preserve has several miles of hike/bike/ski trails, a private lake and two creeks. Modern home in a quiet rural neighborhood. Easy drive on beautiful country roads to the many attractions in the area--less than 10 minutes to Devil's Lake State Park, Lake Wisconsin as well as Devil's Head & Cascade ski areas.