Family-friendly vacation rentals in Winnebago County

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Top-rated family-friendly rentals in Winnebago County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favourite
A well-lit dining area displays a long white table surrounded by wooden chairs with green cushions. A large abstract art piece is centered on the wall, complemented by light streaming through the windows. Hardwood floors are accented by a soft area rug beneath the table.
Apartment in Rockford
4.94 out of 5 average rating, 139 reviews

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

Guest favourite
Two decorative stone lion statues are positioned at the entrance of the brick home. The lion on the left is seated, facing forward, while the one on the right is slightly turned. The front porch features a textured concrete step and a surrounding garden with greenery.
Home in Rockford
4.89 out of 5 average rating, 251 reviews

Charming Boulevard Home Near Downtown & Hospitals

Three Bedroom Brick home with fireplace and outdoor space located in neighborhood along a favorite route for runners/cyclists. 3-6 minutes from Anderson Gardens, UW Sports Factory, Coronado Theater and downtown events. Close to all hospitals and a quick and easy drive to both Sportscores. Second floor bedrooms with dressers and closets. Two have view of river. Kitchen is well stocked for easy meal preparation. Cozy backyard is fenced with brick patio, grill and table. Discounts for Week/Month.

Top guest favourite
The exterior of the countryside cottage is displayed, featuring a charming facade with light gray siding and a welcoming sign. Lush green grass surrounds the home, complemented by landscaped garden beds filled with blooming bushes. A cozy porch is visible, with seating arrangements enhancing outdoor leisure.
Cottage in Rockton
4.97 out of 5 average rating, 259 reviews

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

Guest favourite
A cozy living room is depicted with a gray sofa and a wooden coffee table resting on a patterned area rug. Natural light fills the space through large windows, highlighting the warm wood trim and the adjacent dining area featuring a wooden table and chairs.
Home in South Beloit
4.97 out of 5 average rating, 118 reviews

Beautiful Craftsman Style Home w/ Fenced Yard

Enjoy your stay in this beautifully remodeled Craftsman Style Home. Rich with the character of an abundance of wood trim and paneled ceilings, this home is the perfect place for a relaxed, stress free, memorable stay. Complimentary coffee, tea, and bottled water are included. Other amenities include a bike path, private parking, a fenced yard, use of a grill and laundry. Less than a mile away from the revitalized city of Beloit WI, you will have many options for places to eat and things to do!

Guest favourite
A comfortable living room features a pair of brown leather sofas and a wooden coffee table, arranged over a light rug. A wall-mounted TV displays a scenic image. Natural light filters through the nearby windows, illuminating the space with a warm glow.
Home in Rockford
4.91 out of 5 average rating, 104 reviews

Downtown Fun, 2 Doors from River

Historic home with modern amenities by the river & downtown Rockford. 3 bedrooms, 2.5 bathrooms, pool table gameroom, computer workspace, full kitchen. Ride our beach cruiser along the breathtaking Rock River Bike Path to top attractions including Anderson Japanese Garden, Discovery Center Museum, Burpee Museum, Sinnissippi Riverfront Park—all within 5 minutes. At day end, unwind and entertain your family in the playroom with pool table and big screen TV. Book now to lock in your next getaway!

Top guest favourite
A small outdoor deck features a round red table accompanied by two matching chairs. Lush greenery and hanging plants adorn the area, providing a serene view of the wooded backyard. The soft illumination adds a cozy touch, inviting relaxation.
Home in Roscoe
4.99 out of 5 average rating, 314 reviews

* 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".

Guest favourite
A dining area features a wooden table surrounded by six light-toned chairs. Natural light enters through sliding glass doors, which lead to a patio. A small side table holds a decorative item, and a painting hangs on the wall, adding visual interest.
Apartment in Rockford
4.84 out of 5 average rating, 126 reviews

Splash of Swedish in an Exposed Basement Apartment

Nestled in a family friendly neighborhood, this lower unit with private entrance, offers a quiet stay with friendly neighbors. Fast Wi-Fi and Television with a Peacock subscription are provided. Located near highway 20 offers easy access to the airport and highways 39 and 90. The home is 4 min away from Atwood Park, providing miles of scenic hiking and a rescued bird aviary. A 13 min drive gets you to downtown Rockford with numerous shops, museums, restaurants and views of the Rock River.

Top guest favourite
A spacious outdoor area features a fire pit surrounded by seating. In the background, a large barn with a green and white exterior is visible, set against a serene landscape of lush grass and trees.
Farm stay in Cherry Valley
4.98 out of 5 average rating, 408 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.

Top guest favourite
A striking bedroom features a four-poster bed adorned with red sheets and an illuminated sign that reads 'TRUST ME LOVE ME.' Mirrors are positioned on the wall, reflecting the ambient red lighting, creating an intimate atmosphere within the space.
Home in Rockford
5 out of 5 average rating, 115 reviews

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.

Guest favourite
The game room features a variety of entertainment options, including a ping pong table, a foosball table, and a Skee-Ball machine. Ambient lighting elements enhance the playful atmosphere. Comfortable seating is available in the form of a cozy chair, with an area rug adding a touch of warmth.
Home in Rockford
4.82 out of 5 average rating, 198 reviews

Spacious Cabin-style home w/ Gameroom + Gym!

Welcome to our spacious, yet cozy cabin-style retreat, perfect for both relaxation & entertainment! Enjoy the large yet inviting living room, savor homemade meals in our fully-equipped kitchen, complete with modern appliances. Unleash your inner gamer in our epic Game Room or let the kids explore a world of fun in the dedicated play area. Stay fit on-the-go in our well-equipped home gym, stocked with top-notch equipment. Need to work? Enjoy our dedicated workstation for seamless focus.

Guest favourite
A welcoming living area features a green sofa and a striped armchair, accompanied by a modern white chair. A coffee table stands on a patterned area rug with swirling designs. Natural light enters through a window, while wall art and a framed movie poster enhance the decor.
Apartment in Rockford
4.89 out of 5 average rating, 128 reviews

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

Top guest favourite
A cozy living area features two armchairs and a sofa, complemented by a rustic coffee table. Simple artwork adorns the walls, while light filters through the blinds. A small dining table sits nearby, and a plant adds a touch of greenery to the space.
Apartment in Rockford
4.97 out of 5 average rating, 161 reviews

Stylish 1854 Artist’s Qtrs: Walk to Sports Factory

Creativity - - that elusive, mysterious talent we all admire. Years ago, the Artist’s Quarters was the creative think tank of just such a genius. For decades the rooms were filled with the artist’s works, thoughts and borderline crazy energy. Now, the New Artist’s Quarters has become a re-imagining of the creative genius’s studio. It’s an environment designed for you, filled with art and objects that will inspire your creative soul. Recharge yourself in our Artist’s Quarters.

Popular amenities for Winnebago County family-friendly rentals