Holiday rentals in Winnebago County

4.89 out of 5 average rating, 225 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.

5 out of 5 average rating, 8 reviews

5 Acres of Solitude and Fun!

Escape to our countryside oasis, where luxury meets fun for the whole family! Set on 5 acres, our 6-bedroom, 4-bath, with a fully functional kitchen, is a retreat that feels like home. Outside, an inground heated pool (open middle of May through middle/end of September), offering hours of splashing and soaking under the sun. Nearby, a tranquil koi pond provides a peaceful retreat for quiet moments amidst nature's beauty. If you are seeking relaxation and good times, this destination is perfect.

4.91 out of 5 average rating, 156 reviews

Location+History+Art+Arcade = FUN

ARTISTIC GEM IN THE HEART OF DOWNTOWN RIVER DISTRICT! This unique home is former 1930s gas station designed for entertaining and imagining. It is not just a rental; it’s an experience. Dream kitchen w/concrete countertops & steel island. Exceptional walkability: 1 block to main St; riverfront, farmers market, restaurants, brewery, paths & more! Loads of charm w/skylit ceiling, exposed brick/ductwork, custom mosaic shower, fenced patios. 412 game arcade, painting easel & NEW fireman's pole/loft!

4.93 out of 5 average rating, 45 reviews

Beautifully home with 5 bedrooms

Experience the ultimate vacation in this newly renovated 5-bedroom and 2-bath rental, perfect for families or groups of friends. Enjoy 4 king & 2 twin beds, a LUX eat-in kitchen, private yard, and a screened porch. This rental also offers on-site laundry and a 2-car garage attached to the property. Plus, pets are allowed so you don't have to leave your furry friends behind! Book your stay today and experience the ultimate getaway at this luxurious and well-appointed short term rental.

4.98 out of 5 average rating, 291 reviews

Hidden Gem Spanish Style Villa

Ask about our special, Mon-Thurs, book 2 nights, get a 3rd free! 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.

4.91 out of 5 average rating, 43 reviews

Home in Cherry Valley

Riverside Log Cabin: King B+Hot Tub+Sauna

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.

4.93 out of 5 average rating, 535 reviews

Flat in Rockford

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.

4.95 out of 5 average rating, 66 reviews

Bright at Home

You will be close to everything when you stay at this centrally-located home. Walking distance to shopping plaza that features restaurants, fitness center, Dunkin donuts, and shops. Less than a mile to grocery store and gas station. Main bedroom with Queen Bed and 2 dressers. Second Bedroom with Queen and Twin beds. Livingroom features couch, chairs, and twin futon. BBQ available summer months only. Ranch home with Stairs for entry and stairs to laundry.

4.93 out of 5 average rating, 15 reviews

3 Bedroom's River house with great views

This unique property offers three bedrooms, two and half bath is located on the Rock River with stunning views. All the amenities are upper end and you will feel right at home. Unwind in the whirlpool in the master suite, enjoy an open kitchen and relax on the large deck overlooking the river, sunsets and much more. Take walks around the neighborhood on national avenue and bring the whole family to this great place with lots of room for fun.

4.97 out of 5 average rating, 187 reviews

Business access in residential comfort

Clean, convenient, cozy cape cod style home in quiet neighborhood with fenced back yard. Just minutes drive to highways 20, 39, I90, & SportsCore. I'm willing to adjust check-in/out times if I can, just ask. Message me if you have any questions, or would like to request a long term stay. It is a really pleasant home! Per Airbnb rules, please do not book for someone else. Garage space is available for a fee, please inquire at booking.

4.93 out of 5 average rating, 360 reviews

Loft in Rockford

510 Studios Loft East

Beautiful, newly updated one bedroom loft apartment in busy downtown area. Just steps to restaurants, shopping and entertainment. Gorgeous decor, new furnishings with couch, love seat, dining table and extra comfy king size bed. Bathroom is completely remodeled. Very fun and artsy style, full size kitchen, large outdoor deck, cable TV, Neflix and more! Great place to stay for business and for pleasure in the heart of Rockford.