Vacation rentals in Winnebago

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

Historical Riverfront Mansion: Serenity+Location

This house was built in 1916 and has recently been beautifully renovated. This property was once considered one of Rockford's Mansions because of its large accommodating 3 story size. Come enter the tranquility that this property provides from its riverside views to its endless entertainment possibilities. The moment you drive through the gates and down the tree lined driveway; you know that you have been transferred to a private retreat where you can relax from the city. Inquire for 10+ guests.

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.

Steps from RockRiver•Massage Chair•Arcade•Firepit

Stunning river views set the relaxing tone as you walk in 🏡 💆🏻Rejuvenate w/ a heated massage chair 🕹️Nostalgic fun w/ classic arcade games 🛏️ King bed in each bedroom for ultimate comfort 🍳 Fully equipped kitchen for home cooked meals 🛜 Fast wifi for remote work 🌸6mins-Anderson Japanese Gardens 🍎28mins-Edwards Apple Orchard 🍻7mins-downtown Rockford 🚴‍♀️ 15mins-Rock Cut State Park ✈️12 mins-RFD Int'l Airport This escape offers the perfect blend of relaxation & adventure🏖️

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.

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!

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.

3BR Home Brand New Kitchen and Bath

There’s something special about finding a place that instantly feels like home. The Gilded Cottage is a beautifully updated three-bedroom mid-century retreat in Winnebago, Illinois. It is bright, peaceful, and designed for easy stays. Enjoy quality linens, inviting gathering spaces, and a dedicated kids’ play area. Close to Rockford attractions, wedding venues, and nature preserves, it’s a calm, comfortable home base for any visit.

Hidden Gem Spanish Style Villa

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.

Las Lomas Luxury Home.

Kick back relax and experience the best of two worlds, the luxury and comfort of a 5 star hotel and the warmth and peace of feeling right at home. This stylish space offers a variety of books to read and a wonderful jet tub to enjoy after a long trip or day at work; along with clean and cozy beds. Take advantage of our welcome coffee bar with a nice selection of teas and snacks exclusive for our guest.

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.