Holiday houses in Winnebago County

20ac Farm Close to Town

This Roscoe farmhouse has 4 inviting bedrooms, including 1 king bed, 2 queen beds and 2 twins. The serene surroundings make it the perfect retreat to unwind and relax. Your stay will be comfortable and convenient. Close to downtown Roscoe and only 5 minutes to Interstate 90 interchange this home offers old world feel, with some fresh updates. Come experience the brilliant charm of this sprawling farmhouse where its decorated like CHRISTMAS YEAR ROUND!! celebrate CHRISTMAS at Valley View Farm!!

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

Modern Midtown - Duplex

Stay in this stylish midtown 2BR, designed for families, couples, business travelers, extended stays, and insurance relocations. Fully furnished with a dedicated workspace for an easy stay. • Near parks, hospitals, downtown, dining, casino, and attractions • Sleeps 6 with 1 king bed, 2 twin beds, and a sofa bed • Full kitchen and coffee bar for easy meals and slow mornings • Fast WiFi, smart lock entry, smart TV, and in-unit laundry Book the adjacent duplex too for up to 12 guests total.

Adults-only Red Room retreat with hot tub

Adults-only private getaway on the Rock River with a hot tub, patio, and one-of-a-kind Red Room experience. Perfect for couples wanting privacy, comfort, and something more adventurous than a typical stay. Relax with a scenic river view, enjoy the hot tub, then explore a playful adult-themed space with a St. Andrews Cross, swing, Sybian, and more. Designed for birthdays, anniversaries, date nights, or a private weekend that feels secluded, romantic, unforgettable, and anything but ordinary.

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.

Upscale Urban Retreat 1 Bedroom Apt. 2nd floor

Charm Art Style. Hardwood floors, original woodwork. Secure keypad entry. Spacious cozy apartment with full kitchen and dining room. Owner on adjoining premises. Street parking. Minutes to Sports Factory, downtown nightlife, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory & Sinnissippi Gardens. 5 blocks to river and rec path. Quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. Not suitable for children under 6.

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.

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.

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.

Luxury Wine Barrel Stay at Hidden Creek Estates

The Wine Barrel Home is a design-forward King Suite for two set on the 77-acre grounds of Hidden Creek Estates. Enjoy heated bathroom floors, a tiled walk-in shower, private patio seating, and access to a shared sauna. Walk to our on-site restaurant and wine bar in three minutes, explore 3.5 miles of scenic trails, or simply unplug and settle into the quiet rhythm of the estate.

Phoenix House | Firepit & Big Backyard TV Room

Phoenix House – Modern, spacious, and cozy space to create unforgettable memories. Hi! I'm your host, and I'm so happy to welcome you to Phoenix House, a home thoughtfully designed so you feel comfortable, relaxed, and have everything you need. Here, you'll be able to unwind, spend time with your loved ones, and enjoy a stay you'll always remember.