Vacation rentals in Winnebago County

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Top-rated vacation rentals in Winnebago County

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

Guest favorite
A bright entryway showcases a wooden staircase with a polished handrail, leading to the second floor. Light is provided by a stylish chandelier. The warm-toned walls complement the hardwood flooring, while a small area rug is positioned near the doorway.

Home in Rockford

4.89 out of 5 average rating, 220 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.

Guest favorite
An inviting inground pool is surrounded by a wooden deck adorned with lounge chairs. Soft string lights illuminate the area, creating a tranquil evening ambiance. Lush trees frame the backdrop, enhancing the outdoor space's serenity at twilight.

Home in Rockford

5 out of 5 average rating, 7 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.

Guest favorite
A unique kitchen area features modern appliances and striking red cabinetry. Industrial-style lighting fixtures hang above the kitchen island with seating. Large windows allow natural light to brighten the space, while the textured walls add character to the artistic ambiance.

Home in Rockford

4.91 out of 5 average rating, 151 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!

Guest favorite
A calm river is depicted, bordered by lush greenery. Smooth stones line the water's edge, and a bridge is visible in the background, adding to the scenic view. The clear sky reflects on the gentle surface of the water, enhancing the tranquil setting.

Home in Cherry Valley

4.95 out of 5 average rating, 58 reviews

Victorian*4 poster King*Walk to village*A+ Kitchen

✔︎ Family friendly ✔︎ Fenced yard ✔︎ Generously equipped kitchen ★ "Everything you need and then some is within easy walking distance." ★ "The beds were comfy and there were thoughtful amenities throughout.” ➢ 1 min walk to restaurants, parks, bars, coffee, ice cream, mini grocery store & more ➢ Quiet neighborhood ➢ Onsite washer & dryer ➢ Piano & acoustic guitar ➢ DVDs & games ➢ Grill & outdoor dining ➢ Family owned and managed by longtime village residents ➢ Attentive and friendly hosts

Guest favorite
A spacious living room features a large sectional sofa in a deep blue color, complemented by a small teal chair. A world map adorns the wall above a coffee table, while natural light enters through large windows framed by light gray curtains. Wood flooring adds warmth to the space.

Home in Rockford

4.93 out of 5 average rating, 41 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.

Guest favorite
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

4.98 out of 5 average rating, 284 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.

Guest favorite
An open-concept living area features high wooden ceilings and natural wood beams. A leather sofa and matching lounge chair are positioned around a wooden coffee table, which holds a chess set. The dining area is visible in the background with a large table surrounded by chairs.

Home in Cherry Valley

4.9 out of 5 average rating, 31 reviews

Log Cabin Escape|King B|Hot Tub|Sauna|River Views

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.

Guest favorite

Cottage in Roscoe

4.99 out of 5 average rating, 71 reviews

Cottage with Pond at Hidden Creek Estates

Our Cozy Cottage on 60 forested acres offers 3 miles of manicured trails and fishing in a .5 acre pond. Stocked with brand new kitchen appliances, perfect for cooking meals. With 3 bedrooms and 3 full baths, 10 people can stay comfortably. It's the perfect escape for business or pleasure. Nearby, our cozy wine bar is open Wed-Fri (3 pm - 9 pm) and Sun (11 am - 5 pm) to the public. Inquire for one-room stays or check our other two Airbnbs options on the Estate.

Guest favorite
The exterior of a charming two-story building is depicted, adorned with lush green vines that climb the brick facade. A distinctive front door with glass panels leads to the entryway. Surrounding greenery adds a natural touch to the welcoming entrance.

Apartment in Rockford

4.94 out of 5 average rating, 522 reviews

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.

Guest favorite
A light-filled living room features a comfortable gray couch adorned with decorative cushions, alongside a matching armchair and ottoman. A stylish coffee table rests on a soft area rug. Light curtains frame the windows, and a modern mirror reflects the space.

Home in Rockford

4.95 out of 5 average rating, 63 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.

Guest favorite
A spacious wooden deck is presented with four comfortable lounge chairs positioned toward a serene river view. The scene is framed by lush trees and features an array of autumn colors on the opposite riverbank. The cloudy sky reflects soft light over the water.

Home in Rockford

4.93 out of 5 average rating, 14 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.

Guest favorite
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

4.97 out of 5 average rating, 181 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.

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