Holiday rentals in Hillcrest

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.

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.

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.

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!

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.

Look at the reviews! Julie's House on Main

Super Clean, Quiet and Cozy! Pet friendly... 🐾 🐕 ❤ 🐶 (Applicant + Fee required) 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!

510 East Loft Studios

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.

Urban Elegance, Small Town Charm Suite #1

Lovely, quaint, and full of urban elegance yet all set in a charming small town setting. Amenities of a luxury boutique hotel, yet the low price of a standard room. Complete with WiFi, The kitchen does not have a stove but does host a small fridge, microwave, toaster oven, coffee maker, dishes. Separate living room with Record Player & Vintage Albums. Luxury Bed in a relaxing space. Workspace so you can conduct your business.

Hidden Gem - Rock River

The Eagle’s Nest: A Cozy Family Escape! Unplug and unwind at The Eagle’s Nest, 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, this peaceful retreat offers adventure and tranquility. Book now and escape the city hustle!