Vacation rentals in Winnebago

4.95 out of 5 average rating, 118 reviews

Apartment in Rockford

Hip-N-Colorful Prospect Smoke Free

Excited to offer this space to travelers! We have fun with some color. Queen bed in the first bedroom, XL twin beds in the back bedroom. Great location! Close to stylish, revitalized downtown Rockford with terrific restaurants, night life, shops, and galleries. Upper unit in vintage 4 family with long term tenants below and I live in the other upper. Absolutely no parties. Only registered guests. No smoking inside or outside on the property. Violation results in $500 cleaning fee/poor review

4.96 out of 5 average rating, 240 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

Farm stay in Cherry Valley

4.97 out of 5 average rating, 365 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

4.97 out of 5 average rating, 159 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, 294 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.

4.9 out of 5 average rating, 119 reviews

Apartment in Rockford

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

4.97 out of 5 average rating, 33 reviews

Cottage in Winnebago

Relax. Recharge. Reconnect.

Need a family-friendly spot that feels like home but with a little extra fun? This midcentury gem in downtown Winnebago is cozy, stylish and ready for your next getaway. Close to all the best local spots, it’s perfect for chilling out, playing games and making memories together. What will your family’s favorite corner be? "It was warm, cozy, clean, and so quiet!" "The house has been updated, but also has some of its old charm" “Garage and EV charger were much appreciated!”

4.93 out of 5 average rating, 546 reviews

Apartment in Edgewater

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, 104 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!

4.96 out of 5 average rating, 181 reviews

Cabin in Oregon

GOOSE ISLAND CABIN -Secluded Riverside Eco-Retreat

Nestled along the banks of the Rock River under tall oaks, ye ol cabin was built by early settlers in 1907. Legit rustic charm. Secluded yet only 10 mins from the fun town of Oregon. 100 acres of private property, bordering Lowden-Miller State Forest. Includes use of canoes/kayaks, large riverfront yard, grills, hammocks, deck, porch and firewood. $35/night/person/pet after first 2 people. Message Tim about accomodating big groups and events.

4.95 out of 5 average rating, 437 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.

4.96 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!

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Popular amenities for Winnebago vacation rentals

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Other great vacation rentals in Winnebago

4.63 out of 5 average rating, 159 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 stars8 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.

5 out of 5 average rating, 86 reviews

Adults Only "Red Room" Home with Hot Tub

SamanthaRating, 5 stars1 week ago

Very clean place and it was exactly as described, we will definitely be back soon!

4.94 out of 5 average rating, 64 reviews

Cottage in Oregon

Spacious Hillside Home Overlooking Private Woods

IrinaRating, 5 stars3 weeks ago

This was our second time staying at the Fuller House. We had a magical trip with highlights including getting cozy by the fireplace and listening to records, setting up our tent in the backyard and roasting marshmallows over the fire, reading and napping in the hammock, and spending hours running around the property with our toddler and finding wild flowers, walnut shells, bugs, and swinging on the tree swing. We love this home and Krista and Jeff are very thoughtful and responsive hosts. We had a minor plumbing issue and Jeff came over the fixed it right away. Love this place and will definitely come back!

5 out of 5 average rating, 5 reviews

Guesthouse in Rockford

Cozy RiverView Home

LindsayRating, 5 stars3 weeks ago

Small but well appointed, will definitely rebook if we are back in the area

Superhost

4.5 out of 5 average rating, 12 reviews

Fully furnished 2br updated condo upstairs

MoniqueRating, 5 stars4 weeks ago

From the time I reached out to see if an extended stay was an option Jennifer was really helpful. I needed 3 beds. The majority of the Airbnbs I found in Rockford had 2 beds and a let out couch, I have teen boys. Them sleeping in the same bed for 6 weeks would not have worked for any of us. The bedrooms are spacious, the home smelled good, and was clean. She provides basic cooking and eating utensils and cleaning supplies. The dryer went out and Jennifer promptly responded and replaced it within two days. It’s quiet. There’s a balcony. The neighbors are pretty quiet but nice. They also have roosters lol. Jennifer came by to update the door lock (she messaged beforehand) ….she’s very personable. I came there after being displace due to a fire. This place provided the comfort my children needed and a quick return to normalcy. If u want to feel at home, this is it!