Holiday rentals in Rock City

Doe Meadow, a tiny house farm stay

Doe Meadow is my newest custom designed tiny house nestled along the drive to my family farm. Sharing my little slice of heaven with guests is something I have found great joy in. Rural tourism is my passion, & all the farm animals are anxiously awaiting your visit- treats in tow- of course! I wanted to create something unique, a place to make memories, & somewhere you'll want to come back to. Settle in the hammock, listen to the peaceful wind chimes, watch the goats & mini cows graze, unwind.

Secluded Log Cabin w/ Private Lake & Hiking Trails

Escape to a secluded 50-acre nature retreat featuring a private 3-acre lake, a winding creek, and miles of peaceful forest, prairie, and wetland trails. This cozy log cabin offers comfort, privacy, and space for up to six guests—perfect for families, couples, and nature-lovers alike. Each stay includes full access to our HappyGuest digital guide, featuring aerial maps, trail routes, local highlights, and everything you need to make the most of the house, property, and surrounding community.

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Adults-only Red Room retreat with hot tub

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.

Rustic Barn Loft at Oak Springs Farm

Unplug in our gorgeous barn loft above our working barn. Sleep to the sound of crickets and frogs in the pond, then wake up and pet the sheep, goats, rabbits, cats, ducks & chickens. Open floor plan, cathedral ceiling, farm decor, fire pole, sliding barn doors. Full kitchen, jetted tub, rain shower, laundry. Stone patio, fire pit. 2 bedrooms, sleeper sofa, air mattresses. Juice, coffee, and fresh eggs provided when the hens are laying. NO A/C. ABSOLUTELY NO PETS Facebook oakspringsfarmwi

Sunset Cove LakeHouse-Paddle Boat-HotTub-Billiards

Enjoy the spacious lakefront retreat in Rockford designed for unforgettable family vacations, group getaways, and relaxing weekends on the water. Nestled on a stocked 10-acre lake, this home offers the perfect mix of comfort, entertainment, and outdoor fun-all just minutes from I-90 Whether you're fishing off the dock at sunset, soaking in the hot tub, grilling on the deck, or putzing in the paddle boat, Sunset Cove is the perfect place to relax, reconnect, and enjoy lake life together!

Walk everywhere in downtown Freeport.

Downtown Freeport, walking distance to movies, bars, restaurants. Some of the summer activities include concert on the square once a month, market every Saturday. The largest car show with 1000 old cars, the air show. If you like to walk or ride a bike there’s Jane Adam’s trail. Krape park is beautiful with many trails on the river where you can rent kayaks. The kitchen is apartment sized but boasts a counter top induction cook top, oven, microwave, Keurig,and refrigerator.

KC HOUSE Beautiful ranch in the country!

Relax with the whole family or friends at our peaceful ranch in the country. We have so much to offer. Whether you just need time with friends or a family vacation, we have you covered. You can seclude yourself to the unique ranch themed house or head in any direction and find yourself at a country bar or restaurant. We have stables for you to even bring your horse if you wished! In the winter, the snowmobile trail goes right through by our land. Come check us out!

Cozy Cabin on Decatur Lake

Relax in this cozy cabin on the lake. Fish, hike or even swim (after a short canoe/kayak paddle); just like being Up-North without the drive! Use our canoe or kayaks or bring your own. Cook indoors or out. Near Sugar River Trailhead, Headgates Park and Three Waters Reserve. A few miles away from tubing on the Sugar River. An hour from Madison and 30 minutes from Beloit, Monroe or Janesville. Previously listed by Betty and under her same great management!

3BR Home Brand New Kitchen and Bath

There’s something special about finding a place that instantly feels like home. The Gilded Cottage is a beautifully updated three-bedroom mid-century retreat in Winnebago, Illinois. It is bright, peaceful, and designed for easy stays. Enjoy quality linens, inviting gathering spaces, and a dedicated kids’ play area. Close to Rockford attractions, wedding venues, and nature preserves, it’s a calm, comfortable home base for any visit.

Historic Square Loft | Walk to Restaurants & Shops

Stay on Monroe’s Historic Square—park once and walk everywhere. This bright, quiet downtown loft is steps from coffee, restaurants, shops, brewery tours, and local events. Ideal for couples, professionals, and weekend getaways, with easy self-check-in, reliable Wi-Fi, a dedicated workspace, and a full kitchen. Perfect for Cheese Days, courthouse visits, and downtown weekends. Quiet hours ensure a peaceful night’s sleep.