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Family-friendly holiday 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
The historic limestone home features a welcoming red door and large windows, allowing ample natural light. A snow-covered path leads to the entrance, and a neatly stacked pile of firewood is visible beside the house. Surrounding trees are lightly dusted with snow.
Farm stay in Shirland

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

FamilyIndoor spacesAir conditioning

4.91 out of 5 average rating, 267 reviews
Guest favourite
A stately three-story brick home is displayed, showcasing a spacious patio area with a mixture of shaded and sunny spots. Lush green grass surrounds the property, with well-maintained landscaping complementing the structure. Large windows provide ample natural light, highlighting the inviting outdoor space.
Home in Rockford

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.

Indoor spacesFamilyOutdoor spaces

4.96 out of 5 average rating, 115 reviews
Guest favourite
A golf simulator room is equipped with a large screen displaying a scenic golf course. A golf bag and clubs are positioned nearby on a green carpet, with practice balls scattered in front of the tee area. Dark curtains frame the windows, and walls feature decorative artwork.
Home in Rockford

Golf Simulator • Hot Tub • Arcade • Massage Room

Welcome to the Golfer's Retreat & Arcade, where relaxation & excitement await! Indulge in a few rounds on our golf simulator, perfect for honing your skills or simply enjoying a friendly competition. Then, treat yourself to some well-deserved rest & rejuvenation in our massage chairs, melting away the stress of the day. Immerse yourself in the free-play arcade, where endless entertainment awaits. Get ready for an unforgettable experience for the whole family. Pet fee $50/night per dog-max 2 dogs

KitchenFamilyCheckout

4.98 out of 5 average rating, 104 reviews
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

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

FamilyIndoor spacesLocation

4.97 out of 5 average rating, 287 reviews
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.
Apartment in Cherry Valley

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.

FamilyKitchenHiking

4.97 out of 5 average rating, 476 reviews
Top Guest favourite
Home in Rockton

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.

FamilyKitchenAir conditioning

4.97 out of 5 average rating, 116 reviews
Top Guest favourite
A charming brick building, enveloped by lush greenery, features a welcoming entrance with a secure door. Large windows framed by ivy provide warmth to the facade. Flower beds with colorful plants offer a touch of vibrancy along the pathway leading to the front door.
Apartment in Rockford

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.

FamilyIndoor spacesDecor

4.95 out of 5 average rating, 225 reviews
Guest favourite
Home in Cherry Valley

Riverside LogCabin:Hot Tub|Sauna&King Beds Retreat

Welcome to your perfect getaway! Our house is ideal for couples, families, or small groups looking to escape the hustle and bustle of daily life and reconnect with nature. ★ Relax in Hot Tub ★ Rest in Sauna ★ Sleep - 3 Bedrooms, 5 beds ★ Gather around fire pit with family and friends ★ Rest peacefully in a 3 king-size beds ★ Watch your favorite shows on 4 Roku TV’s around house ★ Stay connected with fast Wi-Fi. ★ Play foosball tournaments ★ Hiking, fishing, kayaking.

KitchenIndoor spacesOutdoor spaces

4.83 out of 5 average rating, 108 reviews
Top Guest favourite
A bright living room features a light-colored sofa and a matching loveseat facing a dark wooden coffee table. A patterned red area rug covers the hardwood floor, while natural light filters through a window with white blinds. Artwork adorns the walls, adding a touch of color.
Home in Rockford

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

KitchenFamilyQuiet

4.95 out of 5 average rating, 114 reviews
Top Guest favourite
The exterior of the bungalow features a welcoming, brick facade with a sloped roof and a prominent front porch. Large windows allow natural light inside, while colorful flowers in the front garden add charm to the entrance.
Bungalow in Rockford

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.

FamilyKitchenWalkability

4.96 out of 5 average rating, 479 reviews
Top Guest favourite
The Spanish-style villa is framed by lush greenery and a landscaped garden featuring stone pathways. Distinctive red windows and subtle lighting enhance the exterior's charm. The upper level is visible, showcasing a unique architectural design that complements the overall aesthetic.
Home in Rockford

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.

FamilyKitchenSleep quality

4.99 out of 5 average rating, 343 reviews
Guest favourite
An inviting living area features a deep blue sofa and two gray armchairs arranged on a patterned rug. A low coffee table sits in front, while a large TV is mounted on the exposed brick wall. Natural light flows through the skylight above.
Loft in Rockford

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.

KitchenFamilyAir conditioning

4.94 out of 5 average rating, 171 reviews

Popular amenities for Winnebago County family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
A hot tub is positioned on a deck overlooking a scenic river view. The water's surface reflects soft light, creating a serene ambiance. A lattice privacy screen is visible in the background, framing the peaceful outdoor setting.
Home in Rockford

Adults-only Red Room retreat with HotTub

KitchenIndoor spacesValue

5.0 out of 5 average rating, 153 reviews
Top Guest favourite
The exterior of a modern farmhouse is showcased, featuring a bright facade with large windows. A white railing and stairs lead to the entrance, while a mature oak tree provides shade, enhancing the property's charm.
Home in Roscoe

Oak View Game Room & Hiking Trails at Hidden Creek

FamilyIndoor spacesLayout

4.92 out of 5 average rating, 113 reviews
Guest favourite
Home in Rockford

Phoenix House | Firepit & Big Backyard TV Room

Indoor spacesKitchenComfort

4.83 out of 5 average rating, 66 reviews
Top Guest favourite
A hot tub is seen filled with bubbling water, situated on a wooden deck. A gas grill is positioned nearby, with a spacious yard enclosed by a white fence. Trees and a clear sky are visible in the background, adding to the outdoor ambiance.
Home in Rockford

Charming Pet-Friendly Rockford Escape

Indoor spacesKitchenParking

5.0 out of 5 average rating, 66 reviews
Top Guest favourite
Home in Rockford

YourKidsMayNeverWantToLeave! GameTable+NEX+HotTub

KitchenFamilyPets

5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Rockford

1920s 6bd Cottage | Hot Tub | Game Room | Fire Pit

KitchenFamilyQuiet

4.91 out of 5 average rating, 43 reviews
Top Guest favourite
Home in Rockford

Spacious family home, Hot tub

Indoor spacesFamilyCondition

5.0 out of 5 average rating, 18 reviews
Superhost
Home in Rockford

Spacious 4BR • 5 Bds •2Bts Ranch for Mid Term Stay

Comfort

Family- and pet-friendly home rentals

Superhost
A warm living area showcases rich wooden accents, featuring a cozy leather sofa and a classic armchair. A coffee table sits at the center with a decorative item. A fireplace is highlighted with a framed art piece above, surrounded by natural light from multiple windows.
Home in Rockford

beautifully restored bungalow | 2 queen beds

KitchenIndoor spacesCheck-in

4.91 out of 5 average rating, 123 reviews
Guest favourite
A cozy living room features a light grey sofa and a wooden table. A television is positioned on a stand, and a patterned area rug complements the space. The open layout allows for a view into the adjacent kitchen area, with natural light illuminating the room.
Home in Rockford

Charming 1930s "Kinsey Farms" Cottage

FamilyKitchenLaundry

4.92 out of 5 average rating, 109 reviews
Top 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

Beautiful Craftsman Style Home w/ Fenced Yard

KitchenIndoor spacesWi-Fi

4.97 out of 5 average rating, 140 reviews
Top Guest favourite
The front of a cape cod style home is shown, featuring a welcoming porch with white railings and hanging flower baskets. The house is surrounded by well-maintained green grass and lush shrubs, with two gabled dormers on the roof adding character.
Home in Rockford

Business access in residential comfort

KitchenFamilyHeating

4.98 out of 5 average rating, 242 reviews
Top Guest favourite
Home in Rockford

Storybook Stay by the River and Gardens

KitchenFamilyAccuracy

4.95 out of 5 average rating, 22 reviews
Top Guest favourite
Home in Rockton

Whispering Woods Estate-relax, recharge, connect

KitchenFamilyAmenities

5.0 out of 5 average rating, 16 reviews
Guest favourite
A single-story house is showcased with a well-maintained lawn and clear blue sky above. The exterior features white siding, large front windows, and black shutters. A driveway leads to a garage on the right, and a fenced area is visible in the background.
Home in Loves Park

Hamkins Corner

Indoor spacesNearbySleep quality

4.88 out of 5 average rating, 16 reviews
Top Guest favourite
The two-story home features a welcoming red front door and a wraparound porch with steps leading to the yard. Surrounded by trees, the property includes a grassy area and a gravel pathway. A garage is visible in the background, adding to the tranquil farmette setting.
Home in Rockton

S & H Farm & Charm

KitchenFamilyBackyard

4.98 out of 5 average rating, 83 reviews

Family-friendly home rentals with a pool

Home in Rockford

Riverfront Nook - with Pool

KitchenFamilyHospitality

4.83 out of 5 average rating, 12 reviewsAn above-ground pool with clear blue water is surrounded by a wooden deck. A hot tub with a cover sits nearby, accompanied by a potted flower arrangement on the deck. Lush green trees provide a backdrop, enhancing the outdoor setting.
Guesthouse in Pecatonica

The Outhouse

KitchenIndoor spacesBathroom

4.8 out of 5 average rating, 71 reviews
Home in Loves Park

7mls HardRock Casino, 2mls RockCut State Prk, pool

Guest favourite
An outdoor pool area is surrounded by a well-maintained patio and wooden fencing. The clear blue water of the pool contrasts with the beige pavers, while a shaded gazebo provides seating nearby for relaxation. Lush greenery enhances the tranquil atmosphere.
Home in Rockford

Pool, Arcade, Hot Tub and more @16th and Aldeen

KitchenIndoor spacesComfort

4.95 out of 5 average rating, 103 reviews
Guest favourite
Home in Rockford

Arcade • Hot Tub • Movie Room Themed House

KitchenFamilyAccuracy

4.98 out of 5 average rating, 41 reviews
Superhost
Home in Rockford

Andy's House *hot tub* *arcade* *theatre*

KitchenFamilyCleanliness

4.97 out of 5 average rating, 29 reviews