
Holiday rentals in Shirland
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Top-rated holiday rentals in Shirland
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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
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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!
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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
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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.
LocationFamilyHospitality

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.
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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.
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Farmhouse in Rockton Sleeps 12-14
Our quiet 10 acre farm is 1 mile from the small town of Rockton with hay and wheat fields on 3 sides . Our neighbors and family enjoy the country life and welcome guests. 1.5 hrs from Chicago. Close to popular wedding venues. Eat in our newly renovated home with large gourmet kitchen. Our farm is perfect for a family with plenty of room for the kids to explore! 2019 Events: 9/7 Urban Farmgirl Main Street Market 9/20 Midway Village WW II Days 8/6-8/11 Boone County Fair
LocationFamilyHiking

Guest House
Take a step away from the everyday hustle and bustle and surround yourself with the sights, sounds, and smells of the country. Our guest house sits amid our family dairy goat farm and will offer you the opportunity to visit animals from goats and horses to chickens, dogs, and cats. We milk around 100 goats with baby goats born February through June. In the summer months you'll find homegrown, fresh produce on our roadside stand.
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Cozy Durand Retreat | Walk to Shops & Dining
Enjoy this charming main-level apartment just steps from downtown Durand. Perfect for a relaxing small-town stay, the space sleeps up to 4 with a queen bedroom and pullout sofa. Features include wifi, a spacious living room, stocked kitchen with dining table, Keurig with K-cups, and laundry. Walk to local shops and dining while enjoying a cozy, comfortable home base for your visit. 1 dog up to 35 lbs allowed with pet fee.
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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.
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Spacious 2BR Apt (Sleeps 6): 2 KING Beds & Balcony
🌟 SPACIOUS APARTMENT FOR 6 (2 KING BEDS) Travel in superior comfort in this spacious upper-level apartment, designed with modern families and groups in mind. ✅ HIGHLIGHTS: 2 King Size Bedrooms, Private Balcony & Assigned Parking. ✅ LOCATION: 5 min to Rock River & 10 min to Rockford Casino. ✅ CAPACITY: Ideal for 2 couples with children (King beds allow for comfortable co-sleeping).
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Clean private safe retreat getaway!
Easy scheduling. No contact check in. High end finishes, quartz countertops/tile shower. Private backyard with deck plus more! finished garage with 600 square feet plus a sliding glass door looking to the backyard. Kitchen has SS appliances. Washer and dryer. There is wifi and extender. No shared spaces. A/C
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Popular amenities for Shirland holiday rentals
Other great holiday rentals in Shirland

Susie's Cottage in Rockton
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Large Home On The Rock River *Pool Table*
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1912 Historic Charm meets Modern Comfort
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Spacious Delightful 2 Bedroom Home
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Mulford Complex Private Estate • Spa & Pool
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The River House in Historic Rockton Illinois
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3BR Home Brand New Kitchen and Bath
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The Ravines • Riverfront A-Frame + Cedar Tub/Sauna
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Destinations to explore
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- Alpine Valley Resort
- Wisconsin State Capitol
- Lake Kegonsa State Park
- University of Wisconsin
- Henry Vilas Zoo
- Lake Geneva Public Library
- Camp Randall Stadium
- Lake Geneva Cruise Line
- Chazen Museum of Art
- Overture Center For The Arts
- Dane County Farmers' Market
- Monona Terrace Community And Convention Center
- Madison Childrens Museum
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Alpine Valley Music Theatre
- Rock Cut State Park
- Big Foot Beach State Park
- Discovery Center Museum
- Nicholas Conservatory And Gardens
- Lake Geneva Ziplines & Adventures





