Holiday rentals in Shirland

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Top-rated holiday rentals in Shirland

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Top guest favourite
A yurt is depicted, nestled among lush greenery. A wooden deck equipped with two chairs and an umbrella provides seating. The entrance features double doors framed by angled wooden roofing, with a wood-burning stove visible on the side. The surrounding forest offers a sense of seclusion.
Yurt in Cambridge
4.98 out of 5 average rating, 239 reviews

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

Top guest favourite
The historic limestone home features a welcoming red door and large windows, allowing ample natural light. A snow-covered path leads to the entrance, and a neatly stacked pile of firewood is visible beside the house. Surrounding trees are lightly dusted with snow.
Farm stay in Shirland
4.91 out of 5 average rating, 259 reviews

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

Top guest favourite
The exterior of the countryside cottage is displayed, featuring a charming facade with light gray siding and a welcoming sign. Lush green grass surrounds the home, complemented by landscaped garden beds filled with blooming bushes. A cozy porch is visible, with seating arrangements enhancing outdoor leisure.
Cottage in Rockton
4.97 out of 5 average rating, 266 reviews

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

Top guest favourite
A spacious outdoor area features a fire pit surrounded by seating. In the background, a large barn with a green and white exterior is visible, set against a serene landscape of lush grass and trees.
Farm stay in Cherry Valley
4.97 out of 5 average rating, 438 reviews

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.

Top guest favourite
An open-concept living space features warm wood paneling and large glass sliding doors offering views of the river. A seating area is arranged with plush cushions, and a wooden table with bar stools is positioned nearby, inviting relaxation while enjoying the serene waterfront scenery.
Cabin in Edgerton
5 out of 5 average rating, 164 reviews

Waterfront modern cabin w/ kayaks

VERY romantic getaway for 2! Enjoy your own private dock, welcome to tie off your own boat or rent locally. Complimentary use of 2 kayaks. Beautiful modern riverfront cabin near Lake Koshkonong's eateries and entertainment. Soak in the gorgeous Wisconsin summer with water activities at your fingertips. The rest of the year take in the pristine wonderland views in our enclosed balcony. Only 30 minutes from Madison's world class culinary experiences, performance arts, sports & festivals.

Top guest favourite
The exterior of a historic one-room schoolhouse is shown, featuring a red front door and a fenced yard. Surrounding trees provide a natural backdrop, and a shed is visible nearby. Soft sunlight enhances the inviting outdoor space, contributing to a peaceful setting.
Place to stay in Brodhead
4.98 out of 5 average rating, 210 reviews

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.

Top guest favourite
A hot tub is positioned on a deck overlooking a scenic river view. The water's surface reflects soft light, creating a serene ambiance. A lattice privacy screen is visible in the background, framing the peaceful outdoor setting.
Home in Rockford
5 out of 5 average rating, 139 reviews

Adults Only "Red Room" Home with Hot Tub

Unique adult themed home with a BDSM / "Red Room" experience. It's a great way for couples to turn their fantasies into reality and explore with each other. Includes St Andrews Cross, Swing, and Sybian! Relax on the patio or in the hot tub with a scenic view of the Rock River. Once you arrive you will not want to leave so we try to provide you with everything you may need for your stay! Frozen pizzas, Bottled Water, Coffee, Robes, Firewood and a special gift with each reservation.

Top guest favourite
Home in Rockton
4.97 out of 5 average rating, 104 reviews

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.

Top guest favourite
Home in Janesville
5 out of 5 average rating, 144 reviews

Fully Renovated 2BR 1BA Gorgeous Exec Home #8ma-R

Enjoy your stay in Janesville, WI in this fully renovated two-bedroom cozy executive home Professionally Managed by Kevin Bush! The location is central to dining, shopping, and popular Janesville spots like the Rotary Botanical Gardens. This home will truly feel like your home away from home. Located just minutes from I39 giving you easy access for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on St. George Lane for more dates. Kevin, Host

Top guest favourite
The tranquil scene captures a vibrant sunset over the lake, reflecting hues of orange and gold on the water's surface. Silhouetted against the colorful sky, two ducks glide peacefully by the shoreline, framed by a quiet lake house and rocky beach area.
Home in Milton
4.99 out of 5 average rating, 130 reviews

Buoys UP! Lake Life & Sunsets

Looking to unwind & enjoy Lake Life-where weekends begin any day of the week-any season you choose? Here at Buoys UP! you will be able to do just that. Enjoy private access to our newly remodeled 2 bedroom lake house at Lake Koshkonong, WI. Overlook the private road this little gem is located on and enjoy the wonderful lake views and the beautiful sunsets. Stroll down the road for apx. a 2 minute walk to take advantage of your personal lake access Buoys UP! offers just for you.

Top guest favourite
An aerial view of the Lil House On The Prairie showcases its modern structure surrounded by lush green landscapes. The well-maintained yard features trees and ample open space, while a gravel driveway leads to the side of the house. The expansive prairie extends into the distance, highlighting the natural beauty of the area.
Cottage in Franklin Grove
4.95 out of 5 average rating, 196 reviews

LHOTP (Lil House On The Prairie)

Lil House On The Prairie (LHOTP) is aptly named because it’s located on the edge of Nachusa Grassland’s 1,000 acre south Bison pasture. The 100+ herd of free ranging Bison can often be viewed right along the boundary fence to the west! This recently remodeled two bedroom cottage can sleep six with two queen size beds and with a pull out sofa bed. LHOTP offers a quiet, convenient, and comfortable place to base your adventures from. Behaved dogs & responsible owners welcome!

Guest favourite
A cozy cabin interior features warm wooden paneling and soft lighting. A brick fireplace adds comfort, while a spacious bed is dressed in a patterned quilt. A inviting sofa and round area rugs enhance the welcoming atmosphere of the living space.
Cabin in Brodhead
4.86 out of 5 average rating, 157 reviews

Cozy Cabin on Decatur Lake

Relax in this cozy cabin on the lake. Fish, hike or even swim (after a short canoe/kayak paddle); just like being Up-North without the drive! Use our canoe or kayaks or bring your own. Cook indoors or out. Near Sugar River Trailhead, Headgates Park and Three Waters Reserve. A few miles away from tubing on the Sugar River. An hour from Madison and 30 minutes from Beloit, Monroe or Janesville. Previously listed by Betty and under her same great management!

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