Vacation rentals in Shirland

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Top-rated vacation rentals in Shirland

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Guest favorite

Farm stay in Shirland

4.89 out of 5 average rating, 218 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

Mar 25 – Apr 1

G$46,759 GYD per night

Guest favorite

Cottage in Rockton

4.95 out of 5 average rating, 188 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

Mar 23 – 30

G$36,190 GYD per night

Guest favorite

Barn in Rockford

4.98 out of 5 average rating, 173 reviews

Charming converted barn north of Rockford, Ill

We'll be delighted to welcome you to our converted barn. Most describe it as "charming." We are grateful for those comments, and we have tried to provide our guests with a safe, restful, and inviting environment. There are two bedrooms upstairs, and a TV room with 2 twin beds/daybeds downstairs. The galley kitchen has brand new appliances. The beds are outfitted with the most healthful, hygienic mattress pads and bedding we could find. The water is certified free of lead, nitrates, or bacteria.

Jul 8 – 15

G$28,727 GYD per night

Guest favorite

Farm stay in Caledonia

4.89 out of 5 average rating, 104 reviews

Country Guesthouse at Wind Ridge Herb Farm

Welcome to Wind Ridge Herb Farm. Enjoy the peace and tranquility of this beautiful historic, Victorian farm. Just minutes from Rockford, Machesney Park and Beloit, the guesthouse is ideal for couples, friends, families or professionals seeking safe, private and quiet accommodations. Conveniently located near I90, Pierce Lake and Rock Cut State Park, great golf courses and biking, restaurants and shopping, Anderson Japanese Gardens, Nicholas Conservatory and Hard Rock Casino are all nearby.

Sep 27 – Oct 4

G$29,218 GYD per night

Guest favorite

Loft in Monroe

4.99 out of 5 average rating, 121 reviews

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

Jul 19 – 26

G$28,380 GYD per night

Guest favorite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 273 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.

Aug 19 – 26

G$20,529 GYD per night

Guest favorite

Home in Roscoe

4.99 out of 5 average rating, 272 reviews

* Travelers Sanctuary 2/2, deck, native garden.

Two bedroom, two bath home, residential street. 1400 sq ft. Self check-in. Central Air. Parking in driveway. 1-acre, wooded backyard. 4 mi to I90/39-Exit Rockton Rd. 11 mi N of Rockford 5 min to forest preserves, grocery. Ideal for biz class guests, couples, families with children over 8 yr . Share a bit about yourself, why in the area, who you are traveling with & that you read & agree to "House Rules". NOTE: The host lives in lower unit, uses separate, private entrance

Mar 28 – Apr 4

G$30,675 GYD per night

Guest favorite

Cottage in Lena

4.95 out of 5 average rating, 157 reviews

Escape to The Countryside @ Kerlin Schoolhouse!

Welcome to Kerlin Schoolhouse! This Stone Cottage was built in 1870 and was originally a one-room schoolhouse! Kerlin Schoolhouse is located in a quiet, private, peaceful setting in the beautiful countryside. Featuring beautiful views with amazing sunrises, sunsets, windmills, and starry nights! Surrounded by corn fields on all 4 sides. The home features an open concept with loft bedroom & loft-style staircase. Featuring a fireplace, firepit & grill (seasonal), and more.

Jun 19 – 26

G$26,871 GYD per night

Guest favorite

Apartment in Rockford

4.94 out of 5 average rating, 451 reviews

Upscale Urban Retreat 1 bedroom, ground Floor

Charming and beautiful ground floor; wood floors and original woodwork. Secure keypad entry. Owner on adjoining premises. Minutes to Indoor Sports Factory, downtown nightlife, restaurants, shops, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory and Sinnissippi Gardens.. 5 blocks to river and rec path. Centrally located quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. High speed internet.

Aug 25 – Sep 1

G$21,240 GYD per night

Guest favorite

Guesthouse in Stoughton

4.94 out of 5 average rating, 330 reviews

Country cabin, birders paradise.

Country cabin with small kitchen, SMALL BATHROOM, large porch, gardens and birds galore. Located in the country just south of Madison WI. Enjoy the country life, quiet yet close enough to the city to enjoy Madison's activities or Stoughton's Opera House. Sauna, Fire pit, hiking, ask about pets. WiFi is available but not reliable, this is a country setting with slow connections. Please communicate with me regarding pets before booking.

Mar 23 – 30

G$19,260 GYD per night

Guest favorite

Barn in Freeport

4.97 out of 5 average rating, 509 reviews

Cute Little Country Guest House

An old barn/machine shed transformed into a great little rustic retreat (which we affectionately call "Westhaven")! A great secluded place to get away from the day-to-day grind. Hiking trails on the premises and possible kayaks. About 5 miles from civilization (town). Come unwind! FRIENDLY DOGS WELCOME (we speak fluent WOOF! :-) ) (Please NO cats!) This is not just a place to stay, but an experience to remember.

Jan 12 – 19

G$22,408 GYD per night

Guest favorite

Apartment in Albany

4.93 out of 5 average rating, 158 reviews

Sugar River Hideaway

Newly renovated, 3-bedroom vacation home located on the Sugar River in downtown Albany. Albany is a quaint little town with a lot to offer. Enjoy tubing/canoeing down the river, a diner, pizza place, Italian restaurant, 3 taverns, and a bowling alley all within the downtown block. With being only 30 miles away from Madison and 17 miles from New Glarus, Albany is a prime location for your stay!

Jan 20 – 27

G$22,900 GYD per night