Family-friendly vacation rentals in Winnebago County

Charming 1930s "Kinsey Farms" Cottage

Your family will be close to everything when you stay at this centrally-located place. Easy highway access and less than 10 minutes from downtown - all the fun Rockford has to offer! Located on a quiet, dead end street. Walk to the playground at Ken-Rock park! Several stores/restaurants nearby. One hour drive to Chicago O'Hare airport, and only 3 miles from Rockford Intl Airport. Lots of recreation in the area including Rock Cut State Park, Anderson Japanese Gardens, and Klehm Arboretum. LGBTQ+!

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

* Travelers Sanctuary 2bed 2bath unit-sf home

Two bedroom, two bath entire first-floor of a single family home. 1350 sq ft. Self check-in. Central Air. Parking in driveway. Host lives in lower unit, separate entrance. 1-acre, wooded backyard. 4 mi to I90/39-Exit Rockton Rd. 11 mi N of Rockford 7-8 minute drive to forest preserves, grocery. Ideal for biz class guests, couples. Safety issues for children under 8 years. Share a bit about yourself, why in the area, who you are traveling with & that you read & agree to "House Rules".

Adults-only Red Room retreat with HotTub

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.

beautifully restored bungalow | 2 queen beds

Our meticulously restored bungalow blends historic charm with modern comfort. If you love the character of older urban neighborhoods, you'll feel right at home here. If you prefer a newer suburban setting, our home may not be the best fit. Enjoy a cup of pour-over coffee, then curl up with a good book from our curated library. This gem features: • Fenced yard • Modern kitchen • Tranquil bedrooms • Pour-over coffee supplies • Luxurious bathroom • Cozy, thoughtfully designed interiors

HD Jameson House at River’s Edge

Nestled on the Rock River, the HD Jameson House, a National Historic Register gem, blends historic charm with modern amenities. Enjoy river views and with quaint shops and restaurants exploring the Village of Rockton is a perfect family-friendly retreat. This haven is surrounded by nature but close to numerous attritions, ideal for a romantic getaway or peaceful escape. The HD Jameson House offers a heavenly retreat, blending past beauty with present allure for everyone in the family.

Mid-Term Ready | 4BR Home, Fast WiFi, Pet-Friendly

Looking for a far away vacation? Or how about a home right next to home? Welcome to our Rockford AirBnB! Even Chicago is within reach when you stay- busses route between Rockford and Chicago every few hours. Shop at Cherry Valley Mall, explore and dream with the koi at Anderson’s Japanese Gardens, get water thrills at Hurricane Harbor Rockford, or even take a nature expedition at Rock Cut State Park! All within 10 miles or less! “Book instantly now and guarantee your stay!!

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.

Your home away from home

Fully remodeled 1940's Cape Cod style house with entertainment, office and sun room. Conveniently located in the heart of Rockford this stylish home is close to shops, restaurants and downtown attractions. It has three bedrooms and two full bathrooms, with an desk in the bedroom of the first floor. The high speed wifi internet, roku ultra and xbox console can make your stay even more enjoyable. Be your own chef in the fully equipped kitchen with new appliances

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.

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.