
Holiday rentals in Steward
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Top-rated holiday rentals in Steward
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Haven Estates_: Cozy Barn, Hot Spa & heated Pool
Enjoy a peaceful countryside retreat at this charming Barndominium set on 6.5 private acres, accommodating up to 8 guests This spacious getaway features an 18' x 36' private pool with a hot spa and a solar-heated pool room for year-round relaxation. The Great Room offers open-concept living with comfortable seating, recreation space, and four sleeper sofas. The cozy bedroom includes a king-size bed, while the fully equipped chef’s kitchen boasts an oversized island & a stove with an air fryer.
4.93 out of 5 average rating, 121 reviews
Skip & Reed's River Retreat
Wonderful riverfront home located just south of Castle Rock on the Rock River in Oregon, IL. Enjoy beautiful views of the river while enjoying the heated pool (open May 15th through Oct 10th). Enjoy fishing off the lower yard. Must love cats as there are friendly outdoor cats! The Oregon area has plenty to do including exploring the nearby state parks, climbing Castle Rock, visiting John Deere's home, antiquing, tubing and boating down the river & enjoying the quaint area shops & restaurants.
5.0 out of 5 average rating, 54 reviews
The Gurler House
Welcome to Downtown DeKalb’s most charming and highly-rated historic stay! This beautifully restored home offers both modern comfort and vintage charm. The Gurler House, built in 1857, is on the National Register of Historic Places. This lovingly updated home sits back in a gorgeous park-like setting surrounded by nature. While nestled in a peaceful neighborhood, it is only 2 blocks from the Egyptian Theatre and all the downtown shops and restaurants and only a couple minutes away from NIU.
4.98 out of 5 average rating, 57 reviews
Luxury Meets Cozy
Experience the perfect blend of luxury and comfort at our premier ranch house, designed with sophistication and relaxation in mind. Recently renovated with an eye for detail, this exquisite property is ideal for both festive gatherings and intimate romantic escapes. Nestled amidst lush greenery, the house boasts a sprawling backyard that serves as the ultimate entertainment haven. Every element has been thoughtfully considered to ensure your stay is not only memorable but truly unparalleled.
4.98 out of 5 average rating, 61 reviews
Pets-Sleeps 7- Event Room Rochelle
Super Clean, Quiet & Cozy! 🐕Pet friendly 🙂Event Room Available -Ask!! (Additional fee ) 90 mi to Chicago! 2 hrs to the Dells! 5 min west of Hwy 39/51 15 min to NIU 45 min to Rockford Walking and bike trail nearby! Beautiful home! Super clean! Monday-Sat check: 3 PM Sunday Check-In: 5 PM Our eight-jet power shower will relax those tired muscles after a full day of activity. A soak in our modern,free-standing tub will sooth and your worries away. A well stocked kitchen awaits you!
4.96 out of 5 average rating, 156 reviews
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.
5.0 out of 5 average rating, 155 reviews
Family-Friendly Home in Rochelle
Welcome to this spacious, renovated 3-bed, 2.5-bath home in the heart of Rochelle! With an open single-level floor plan, large kitchen, and two fireplaces, it’s perfect for families or professionals. Enjoy the outdoor deck, yard, and grill. Walk to downtown, restaurants, parks, and the hospital. Only 1 mile from Rochelle Railroad Park and under 2 miles from Chicagoland Skydiving. Fast 500mb WiFi, smart TVs, and kid-friendly amenities. Quiet, safe neighborhood—your ideal home away from home!
4.97 out of 5 average rating, 38 reviews
Cozy Cottage Oasis in Charming Grand Detour
This rustic 3 bedroom country house hosts a relaxing getaway & friendly gatherings. Settled on 2 acres in a quaint, historic village, there are no street lights and unfiltered views of the stars. Get away from the crowds, relax & enjoy ample outdoor space, including a fire-pit and charcoal grill. Hike, canoe, and explore the nearby rolling hills, forests & river valleys. Close to John Deere, Lowden and Castle Rock State Park, and Nachusa Grasslands. 10 min drive to Dixon and Oregon IL.
4.74 out of 5 average rating, 176 reviews
Creek Cabin Retreat•3BR Getaway
This modern cabin style home is a spacious 3 story, 3 bdrm, 3 bath & 3 beds in loft. Perfect family & friends getaway. IDNR 700 ac Franklin Creek State Natural Area surrounds the property. Out the backdoor •hiking • trail running • birding • hunting •fishing •XC skiing •photography •equestrian activities •Historic Franklin Creek Grist Mill •TNC's 3,000 acre Nachusa Grasslands is a restored natural Illinois prairie with 70+ American Bison just 2 miles away. •Fine dining nearby
4.93 out of 5 average rating, 126 reviews
Rock River Retreat - The Overlook
Welcome to our remarkable riverfront retreat perched above the Rock River, featuring one of the most scenic views in Northern Illinois. Relax at the custom bar top, enjoy fishing and canoeing, or take in unforgettable sunsets from two observation decks and the Riverview Suite’s panoramic views. Whether you're planning a relaxing escape, outdoor adventure, or memorable gathering with family and friends, this scenic retreat offers the perfect backdrop to unwind in total comfort.
4.93 out of 5 average rating, 14 reviews
Hidden Gem - Rock River
The Eagle’s Nest: A Cozy Family Escape! A renovated cabin on stilts nestled on 5 private wooded acres with stunning views of the Rock River and Kyte Creek—just 5 minutes from Oregon, IL! Hike, fish, kayak, or relax by the firepit under the stars. Perfect for families and outdoor lovers. Book now and escape the city hustle! For price transparency, the nightly rate includes a 15.5% Airbnb service fee and a flat $80 cleaning charge to cover the cleaning service bill.
4.96 out of 5 average rating, 256 reviews
Modern Country Escape | Minutes from NIU
Modern retreat in Malta, IL just 5–10 minutes from NIU & Huskie Stadium! Perfect for parents, alumni, and fans visiting campus, as well as healthcare professionals on local assignments. Enjoy a bright open living area with smart TV, a fully equipped kitchen & coffee bar, cozy bedrooms with fresh linens, fast WiFi, and a quiet neighborhood. Close to downtown DeKalb dining, shopping, and hospitals for both short and long stays.
4.69 out of 5 average rating, 26 reviewsPopular amenities for Steward holiday rentals
Other great holiday rentals in Steward

Little Rock Woods Retreat
5.0 out of 5 average rating, 39 reviews
Warm & Peaceful 2BR Home, Heart of Sycamore
4.97 out of 5 average rating, 68 reviews
Bed and Breakfast with Horse Hotel at VRR
4.97 out of 5 average rating, 487 reviews
Charming 1940s Brick Bungalow
5.0 out of 5 average rating, 45 reviews
The River House
5.0 out of 5 average rating, 24 reviews
The 1870 A Historic Downtown Sycamore Home
4.99 out of 5 average rating, 69 reviews
Cozy Farmhouse on Campus
4.76 out of 5 average rating, 33 reviews
Spacious 4BR Getaway • 3 Acres Near Sycamore
5.0 out of 5 average rating, 22 reviewsDestinations to explore
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