Holiday rentals in Shirland

Historic limestone farmhouse, nature preserve.

Historic 1840's limestone home ,once owned by Sidney Smith, first nationally syndicated cartoonist of The Gumps. Located on 19 acres adjacent to 500 acre wetland conservation area with miles of hiking/skiing trails along the pristine sandy Sugar River for canoeing, birdwatching, or fishing. Ideal for star-gazing, with minimal lighting from neighbors. Enjoy the outdoors from stone patio, including tables, BBQ, and seating for 15, with fireplaces indoors and outside. Sand pile and toys nearby

Country Farm Cottage

Cozy farmhouse Country Cottage on a historic private farm setting. Safe, quiet, peaceful space to relax. Minutes to golfing, hiking, antiques, canoeing, camping, parks, or use as writers retreat. Rockton has great shopping & dining, 20 min to trendy eateries in Beloit WI. Close to local wedding venues Wineries 25 min away May- Nov: orchards cider & donuts Child friendly Visit our Goats Wifi & Roku TVs No Smoking inside No Pets Farm animals and pets on the farm Host lives on same farmstead

Beautiful Craftsman Style Home w/ Fenced Yard

Enjoy your stay in this beautifully remodeled Craftsman Style Home. Rich with the character of an abundance of wood trim and paneled ceilings, this home is the perfect place for a relaxed, stress free, memorable stay. Complimentary coffee, tea, and bottled water are included. Other amenities include a bike path, private parking, a fenced yard, use of a grill and laundry. Less than a mile away from the revitalized city of Beloit WI, you will have many options for places to eat and things to do!

Spacious Executive 2BR Home Near Shopping & Dining

Professionally Managed by Kevin Bush, this rental is nestled in a safe and quiet neighborhood in a desired location that is convenient to Woodman’s Center, Janesville shopping and dining destinations. Enjoy the city’s hundreds of acres of tranquil parkland, miles of peaceful trails, and beautiful downtown riverwalk. Bonus: This location is an easy drive for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on Margate Drive for more dates. Kevin, Host

Adults-only Red Room retreat with HotTub

Adults-only private getaway on the Rock River with a hot tub, patio, and one-of-a-kind Red Room experience. Perfect for couples wanting privacy, comfort, and something more adventurous than a typical stay. Relax with a scenic river view, enjoy the hot tub, then explore a playful adult-themed space with a St. Andrews Cross, swing, Sybian, and more. Designed for birthdays, anniversaries, date nights, or a private weekend that feels secluded, romantic, unforgettable, and anything but ordinary.

Whispering Woods Estate-relax, recharge, connect

Peaceful country home set of 12 wooded acres close to local wedding venues. The atmosphere is beautiful in this spacious country home. The floor plan is open so you can enjoy wonderful conversation and camaraderie with your family and friends. Enjoy grilling and eating on the deck surrounded by beautiful scenic woods. The house will sleep 10 people. It has a King and two queen bedrooms. In addition, there are two pull out couches with queen beds. Well-behaved pets are welcome.

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

HD Jameson House at River’s Edge

Nestled on the Rock River, the HD Jameson House, a National Historic Register gem, blends historic charm with modern amenities. Enjoy river views and with quaint shops and restaurants exploring the Village of Rockton is a perfect family-friendly retreat. This haven is surrounded by nature but close to numerous attritions, ideal for a romantic getaway or peaceful escape. The HD Jameson House offers a heavenly retreat, blending past beauty with present allure for everyone in the family.

Charming Cottage!

Freshly & fully modern retreat offers far more comfort and style than any hotel. It’s the perfect home base, a cozy haven for short-term “between homes” stays, and an ideal launchpad with easy I-90 access. You’ll be close to shopping, dining, medical facilities, and just minutes everything fun!. Inside, you’ll find 2 welcoming bedrooms—a queen bed & a full-sized bed. Outside, a stunning new living space awaits, offering unmatched ambiance for relaxation.

Las Lomas Luxury Home.

Kick back relax and experience the best of two worlds, the luxury and comfort of a 5 star hotel and the warmth and peace of feeling right at home. This stylish space offers a variety of books to read and a wonderful jet tub to enjoy after a long trip or day at work; along with clean and cozy beds. Take advantage of our welcome coffee bar with a nice selection of teas and snacks exclusive for our guest.

Luxury Wine Barrel Stay at Hidden Creek Estates

The Wine Barrel Home is a design-forward King Suite for two set on the 77-acre grounds of Hidden Creek Estates. Enjoy heated bathroom floors, a tiled walk-in shower, private patio seating, and access to a shared sauna. Walk to our on-site restaurant and wine bar in three minutes, explore 3.5 miles of scenic trails, or simply unplug and settle into the quiet rhythm of the estate.