Holiday rentals in Shirland

4.9 out of 5 average rating, 244 reviews

Farm stay 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

4.96 out of 5 average rating, 241 reviews

Cottage in Rockton

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

4.95 out of 5 average rating, 44 reviews

Home in Beloit

1912 Historic Charm meets Modern Comfort

ENTIRE HOME RENTAL-USE OF TWO ROOMS-Not Shared Space. This cinder block home boasts original hardwoods that bring instant comfort and warmth. While on a main drag, traffic is no drag. Sounds beyond struggle to penetrate this fortress. Rest deeply and awake to a home flooded in natural light through large original windows. On chilly mornings enjoy a cup of gourmet coffee in front of the beautiful electric fireplace. The home's authentic beauty remains central. Enjoy snacks, comfy bed, 65" TVs.

4.99 out of 5 average rating, 175 reviews

Loft in Monroe

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.

Farm stay in Cherry Valley

4.97 out of 5 average rating, 368 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.

Place to stay in Brodhead

4.98 out of 5 average rating, 160 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.

4.9 out of 5 average rating, 119 reviews

Fun Retro Apartment in Downtown Rockford

Close to all the action, you are steps away from top restaurants, night life, theaters, sports and the river. Freshly updated space with an extra touch of all things we love 80's, you will find an Atari 5200 with favorites like Pac Man along with your favorite VHS tapes like Breakfast Club and Sixteen Candles. We have a dedicated work area in second bedroom. Great for a quick trip or long work stay. Located steps from Abreo Restaurant, all guests receive 10% discount during stay

4.93 out of 5 average rating, 548 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.

4.88 out of 5 average rating, 105 reviews

Cabin in Brodhead

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!

4.95 out of 5 average rating, 438 reviews

Bungalow in Rockford

Arts and Crafts Bungalow with Outdoor Space

We welcome you to a centrally located two-bedroom Arts & Crafts Bungalow. Ideally situated near sports venues, shopping, museums, and restaurants, the house is a perfect place for families, professionals, and couples. We have free on street parking in front of the home, We are 10 minutes away from the UW Sports Factory, Anderson Japanese Gardens, and Nicholas Conservatory. We are 20 minutes away from Anna Page Park and Rock Cut State Park.

4.7 out of 5 average rating, 10 reviews

Guest house in Rockford

1 Cozy and peaceful place

Kick back and relax in this calm, stylish space. Perfect place to relax after work. This is a guest small duplex house semi-attached to the main home. We are located near the Lowes Distribution Center, the Chicago-Rockford International Airport, about 20-minute drive to the Byron Plant, and about 6-to-8-minute drive to downtown Rockford, Discovery Center, Coronado Theatre, BMO Center, and about 12 minutes away from Swedish American Hospital.

4.83 out of 5 average rating, 54 reviews

Breeze in the City

Beautiful 1 bedroom apartment. 3 minutes from Rockford's Midtown District, 8 Minutes from BMO Center and Coronado Theater. The location is known for some of Rockford's most authentic restaurants, boutique shops, pubs, bars, and bakeries. We offer everything you need for a comfortable stay. We require 2 hours notice for same day booking.

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Popular amenities for Shirland holiday rentals

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Other great holiday rentals in Shirland

4.75 out of 5 average rating, 12 reviews

Home in Machesney Park

Great cozy little house (pets welcome)

GlendaRating, 5 stars3 weeks ago

Great location next to everything you may need. Tin was very helpful and even brought over a flower basket to put on the front steps during our stay.

5 out of 5 average rating, 9 reviews

Cabin in Brodhead

Avail Labor Day-Private Reserve, King Bed, Fishing

RitaRating, 5 stars3 weeks ago

The location and home were great. The view from every corner was scenic. We were able to watch wildlife and take quiet walks around the lake and on the nature trail. There were lots of games to play inside but we enjoyed the beautiful weather and spent our time outside on the lake in the paddle boat and kayaks. The kitchen was plenty big and we were also able to spread out in the other rooms for alone time. We will definitely be back.

5 out of 5 average rating, 19 reviews

Flat in Freeport

Walk everywhere in downtown Freeport.

LukeRating, 5 stars1 week ago

A fantastic price for a convenient location! The inside is spacious with all the amenities you could need. The outside can look a bit uninviting, but the room itself, as well as Judy, were fantastic!

4.81 out of 5 average rating, 43 reviews

Home in Janesville

Entire House Janesville Wi

MelanieRating, 5 stars1 month ago

Was in town for a comedy festival. This spot was a great location and was in a quiet peaceful area while still being close to everything we wanted to do. Instructions for check in/check out were super easy to follow. Very comfortable stay!

5 out of 5 average rating, 4 reviews

Home in Machesney Park

Home On The Rock River *Outdoor Space*

DavidRating, 5 stars7 months ago

I’m Glad I found their house. It was well furnished, peaceful, and I love the glass walls. Perfect place for a family of 6.

5 out of 5 average rating, 10 reviews

Guest house in Rockford

Shelby’s garden cottage.

RyanRating, 5 stars1 month ago

Shelby’s Garden Cottage is the perfect spot for a couples getaway! A chance to get out of the city, this cozy cabin sits on top of a quiet hill next to its owners house, Buddy. Buddy was an incredible host- responsive, attentive, welcoming, yet gave my partner and I privacy to be undisturbed. As a baker, Buddy provided 2 sets of delicious sugar cookies and honey straight from the beehive of the farm this spot is located on. I could go on and on about how amazing our stay was, but I invite you to experience it yourself. Cheers to Buddy and I know for a fact we’ll be back again soon!!!

Home in Janesville

5 out of 5 average rating, 5 reviews

The Mayfield House

RichardRating, 5 stars3 days ago

What an absolute charming home ! If you’re looking in the Janesville area, you will not be disappointed, BethAnd Eric were great hosts and went above and beyond to exceed our expectations. For the first time we brought one of our dogs with us to an air bnb and even he had the amenities and treats waiting for him ! Absolute awesome experience, thank you .