Vacation rentals in Winnebago

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

Franklin's Urban Retreat in the heart of downtown

Live the urban city life in this centrally located loft designed with tons of local art and custom built furnishings. Our loft of is an open floor plan with tall exposed ceilings and brick. Have fun playing our full size retro Arcade and slot machine. And when ready to sleep, you are gonna LOVE the Saatva mattress. Located right in the middle of all the downtown action surrounded by the best restaurants and activities. Located above Abreo Restaurant, all guests receive 10% discount during stay

Cozy RiverView Home

Keep it simple at this peaceful and conveniently located place. Fully furnished, completely private home one bedroom with Queen bed, full bathroom (tub/shower) sink, toilet, your own washer and dryer. It has a full kitchen with dining area, livingroom with wifi Roku tv. My place is a riverfront property that has beautiful views of the Kishwaukee River, it's a very peaceful dead end Street in a safe quiet neighborhood. Conveniently located with ease of access to anwhere in the Rockford area.

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.

Adults Only "Red Room" Home with Hot Tub

Unique adult themed home with a BDSM / "Red Room" experience. It's a great way for couples to turn their fantasies into reality and explore with each other. Includes St Andrews Cross, Swing, and Sybian! Relax on the patio or in the hot tub with a scenic view of the Rock River. Once you arrive you will not want to leave so we try to provide you with everything you may need for your stay! Frozen pizzas, Bottled Water, Coffee, Robes, Firewood and a special gift with each reservation.

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.

Harvest Haven- Cozy Downtown Winnebago Retreat

🍂 Welcome to The Gilded Cottage, your Harvest Haven in Winnebago! This charming 3BR retreat offers cozy living spaces, a dedicated kids’ play zone, premium bedrooms, and a fully equipped kitchen. Relax on the porch, dine on the back patio, or explore nearby Rockford attractions, wedding venues, and scenic preserves. Family-friendly comfort and small-town charm make this the perfect fall getaway. 🍂

beautifully restored bungalow | 2 queen beds

Tucked in the heart of Rockford, our meticulously restored bungalow is a haven of historic charm and modern sophistication. Enjoy a cup of pour over coffee in the morning and curl up with a good book from our in house library. This gem features a: fully fenced yard, modern kitchen, curated library, tranquil bedrooms, coffee supplies, luxurious bathroom, cozy decor, & proximity to the hospital.

Modern 3BR Retreat

Welcome to your home away from home! This stylish 3-bedroom, 1-bathroom house blends modern design with cozy vibes — perfect for families, friends, or remote workers. You'll love the open-concept living space, sleek kitchen with stainless steel appliances, and comfy bedrooms designed for restful nights. The bathroom is fresh and functional, stocked with plush towels and essentials.