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Holiday rentals in Winnebago County

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Top-rated holiday rentals in Winnebago County

Guests agree: these stays are highly rated for location, cleanliness and more.

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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
4.9 out of 5 average rating, 269 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 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
4.91 out of 5 average rating, 259 reviews

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

Top guest favourite
Home in Rockford
4.95 out of 5 average rating, 108 reviews

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.

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, 322 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.
Flat in Rockford
4.83 out of 5 average rating, 137 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
4.97 out of 5 average rating, 442 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 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
5 out of 5 average rating, 140 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.

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.
Flat in Rockford
4.96 out of 5 average rating, 192 reviews

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.

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
4.96 out of 5 average rating, 455 reviews

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.

Guest favourite
A bright living space features a light-colored sectional sofa and a round coffee table with decorative items. Large sliding doors open to a private outdoor area, allowing natural light to illuminate the room. Soft neutral tones and decorative accents create a serene atmosphere.
Home in Rockford
4.94 out of 5 average rating, 54 reviews

Luxury Condo | King Bed | 2BR 2BA | Great Location

Welcome to your luxury two-bedroom condo in Rockford, Illinois. This stunning residence boasts a contemporary design, with sleek finishes and state-of-the-art amenities, perfect for your time in Rockford. The unit if fully stocked with the following: → High Speed Wi-Fi → Two King Beds → 70" Living Room Smart TV → 55" Two Bedroom Smart TV → Dedicated Workspace → Fully stocked kitchen → Washer & Dryer → Private Parking

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
4.99 out of 5 average rating, 335 reviews

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.

Top guest favourite
A warm living area is showcased with a large bookshelf filled with a variety of books. Comfortable seating, including two armchairs and a sofa, surrounds a decorative area rug. A cozy fireplace is centered beneath a wall-mounted television, while a Christmas tree adds a festive touch near the window.
Home in Rockford
5 out of 5 average rating, 144 reviews

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.

Popular amenities for Winnebago County holiday rentals