Vacation rentals in Winnebago

4.96 out of 5 average rating, 242 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

4.99 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, 371 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, 161 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.

4.98 out of 5 average rating, 295 reviews

Hidden Gem Spanish Style Villa

Ask about our special, Mon-Thurs, book 2 nights, get a 3rd free! Unique to Northern Illinois, this Spanish style Villa sleeps 10+ , boasts five patios, a Cantina, 7 ARCADES, HOT TUB, and many surprises you will find as you look at every turn to something unexpected. This property is filled with beautiful furnishings, featuring a balcony off of the upper level that boasts a 12 foot ceiling. Everything from two walk in showers, a jet tub and a hot tub for any level of self-care desired.

Superhost

4.83 out of 5 average rating, 168 reviews

Spacious Cabin-style home w/ Gameroom + Gym!

Welcome to our spacious, yet cozy cabin-style retreat, perfect for both relaxation & entertainment! Enjoy the large yet inviting living room, savor homemade meals in our fully-equipped kitchen, complete with modern appliances. Unleash your inner gamer in our epic Game Room or let the kids explore a world of fun in the dedicated play area. Stay fit on-the-go in our well-equipped home gym, stocked with top-notch equipment. Need to work? Enjoy our dedicated workstation for seamless focus.

4.9 out of 5 average rating, 175 reviews

Perfect Comforts of Home away from Home.

Perfect for traveling professionals or guests who are in town for sport events or other family/social events. . The apartment is newly remodeled and upgraded with the charm and comfort of home on a quiet neighborhood street. The apartment has all the amenities of home. Conveniently located near Swedish American Hospital, University of Illinois School of Medicine, and UW Sports Factory. 15 minutes from MercyHealth Sports Core 2. 10 minutes Chicago/Rockford International Airport.

4.93 out of 5 average rating, 549 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.

4.99 out of 5 average rating, 140 reviews

Historic 1854 Maid’s Qtrs.- A peaceful retreat

If you love old houses like we do, come stay here and feel the history, the wisdom, the unique character oozing out of every 170 year-old brick or creaking floorboard. We have painstakingly renovated these quarters for your comfort, without losing the sense of ages past. So come and enjoy all the creature comforts as well as the twisting stairway and cozy rooms that will promise to transport you to another century! You won’t soon forget the Peck House!

4.95 out of 5 average rating, 439 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.

4.94 out of 5 average rating, 373 reviews

Loft in Rockford

510 Studios Loft East

Beautiful, newly updated one bedroom loft apartment in busy downtown area. Just steps to restaurants, shopping and entertainment. Gorgeous decor, new furnishings with couch, love seat, dining table and extra comfy king size bed. Bathroom is completely remodeled. Very fun and artsy style, full size kitchen, large outdoor deck, cable TV, Neflix and more! Great place to stay for business and for pleasure in the heart of Rockford.

4.96 out of 5 average rating, 214 reviews

Cabin in Oregon

Hidden Gem - Rock River

The Eagle’s Nest: A Cozy Family Escape! Unplug and unwind at The Eagle’s Nest, a renovated cabin on stilts nestled on 5 private wooded acres with stunning views of the Rock River and Kyte Creek—just 5 minutes from Oregon, IL! Hike, fish, kayak, or relax by the firepit under the stars. Perfect for families and outdoor lovers, this peaceful retreat offers adventure and tranquility. Book now and escape the city hustle!

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Winnebago vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Winnebago

4.9 out of 5 average rating, 39 reviews

Cabin in Pearl City

Getaway cabin w/loft & firepit @The Rustic Retreat

SheriRating, 5 stars1 week ago

Enjoyed watching the sunset, listening to summer sounds, and stargazing. Thanks!

5 out of 5 average rating, 20 reviews

Apartment in Freeport

Walk everywhere in downtown Freeport.

RebeccaRating, 5 stars2 weeks ago

Always a great stay! Cozy and close distance to about anything… clean and efficient! Judy is great to work with and always quick to respond. See you, next trip!

Superhost

4.76 out of 5 average rating, 17 reviews

Small private home. Comfy. Unassuming. Classy.

AshleyRating, 5 stars3 months ago

Michael was a wonderful host. He always responded right away and worked with us. The house was just right for my coworkers and myself. if we are ever in the area again we will definitely stay there.

4.62 out of 5 average rating, 161 reviews

Experience Our Relaxing Riverhouse

JessicaRating, 5 stars1 month ago

If we come back to Rockford, we would definitely stay at this location agian! So beautiful, relaxing, affordable wmin a great private location.

4.89 out of 5 average rating, 206 reviews

Guest suite in Rockford

Historic Downtown Riverfront Suite

PeterRating, 5 stars9 months ago

Very nice place, as advertised. Was in town for wedding and Embassy Suites was full, but was able to stay here which was walking distance to hotel at half the price for a quieter and more complete room. Easy walk through downtown Rockford with everything you need for a a stay. Would highly recommend for anybody who needs to stay in this area.

4.82 out of 5 average rating, 39 reviews

Upscale apartment in Rockford!

BobbyRating, 5 stars3 days ago

Bonnie’s place was clean, well-stocked, and in a great location! Bonnie was also very responsive and flexible- would absolutely recommend and stay again!

5 out of 5 average rating, 5 reviews

Charming 2 bedroom Apartment

HuuquocRating, 5 stars3 weeks ago

the building look old but the room is nice and clean, the kitchen and bathroom are new and We ve got everything for a nice and comfortable stay. Thanks Jhonathan,

Superhost