Vacation rentals in Winnebago County

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.

Whispering Woods Estate-relax, recharge, connect

Peaceful country home set of 12 wooded acres close to local wedding venues. The atmosphere is beautiful in this spacious country home. The floor plan is open so you can enjoy wonderful conversation and camaraderie with your family and friends. Enjoy grilling and eating on the deck surrounded by beautiful scenic woods. The house will sleep 10 people. It has a King and two queen bedrooms. In addition, there are two pull out couches with queen beds. Well-behaved pets are welcome.

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, ground Floor

Charming and beautiful ground floor; wood floors and original woodwork. Secure keypad entry. Owner on adjoining premises. Minutes to Indoor Sports Factory, downtown nightlife, restaurants, shops, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory and Sinnissippi Gardens.. 5 blocks to river and rec path. Centrally located quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. High speed internet.

1 Cozy and peaceful place

Kick back and relax in this calm, stylish space. Perfect place to relax after work. This is a guest small duplex house semi-attached to the main home. We are located near the Lowes Distribution Center, the Chicago-Rockford International Airport, about 20-minute drive to the Byron Plant, and about 6-to-8-minute drive to downtown Rockford, Discovery Center, Coronado Theatre, BMO Center, and about 12 minutes away from Swedish American Hospital.

Shelby’s garden cottage.

Shelby’s cottage has been part of Bluffs on the bend farm for over 65 years. It has undergone a complete overhaul and update with all the modern conveniences while retaining a country cottage charm. It is the perfect getaway for a couple. The location is next to the historic ( originated in 1924 ) Kilbuck Bluffs Forest Preserve. While being nestled in the country it is centrally located to restaurants , bars and shopping.

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.

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.