Holiday houses in Rock City

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.

Family · Value · Hot tub

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.

Location · Value · Hospitality

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

Value · Family · Hot tub

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Value · Family · TV

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

Family · Value · Check-in

Pool Table + Ping Pong | Fireplaces | Hot Tub

Escape to this spacious 4-bedroom, 5-bath luxury retreat in the Apple Canyon Lake community—perfect for relaxing, reconnecting, and enjoying time together with beautiful lake views and incredible gathering spaces throughout the home. ✨ HIGHLIGHTS • Stunning wraparound stone fireplace 🔥 • Basement game room with pool table, ping pong, foosball + darts 🎯 • Huge wall of windows + soaring ceilings • Large Smart TVs + fast WiFi • Minutes to golf + dining ⛳ • 12pm check-in & check-out

Family · Checkout · Comfort

Charming Pet-Friendly Rockford Escape

Spacious family-friendly home with a fenced yard—perfect for pets! Enjoy a fully equipped kitchen, gas fireplace, washer/dryer, and BBQ grill. Minutes from the ice rink, restaurants, Aldeen Golf Club, and shopping. Close to: Walking distance to Starlight Theater, Hard Rock Casino (4.7 mi), Sportscore 2 (3.1 mi), Sportscore 1 (6.5 mi), UW Health Sports Factory (7.4 mi), IRONMAN 70.3 Rockford (5.5 mi), and Byron Nuclear Station (27 mi). Ideal for relaxation or adventure!

Family · Value · Getting around

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!

Location · Family · Bathroom

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!

Family · Location · Checkout

The Dairy at the Wegmueller Farm

Welcome! You are about to experience life on an active 4th-generation farm nestled in the rolling hills of Green County. Meet the cows, feed the pigs, befriend a horse, or just enjoy the relaxing and peaceful serenity of rural Wisconsin farm life. Located less than five miles from Monroe, this home away from home is close enough to all that Monroe & the surrounding community has to offer, but still has room to stretch your legs.

Value · Family · Biking

The Car Wash Inn A Unique Stay

Enjoy a unique stay inside a beautifully revitalized single bay 1950s car wash. Only minutes away from historic downtown Shullsburg. This space has been thoughtfully designed to retain it's industrial charm with a nostalgic ambiance, while offering modern amenities for a comfortable stay. ~20 miles to Galena, IL ~25 miles to Mineral Point, WI ~25 miles to Dubuque, IA ~ATV Trail Access with large parking area

Location · Value · Layout

Las Lomas Luxury Home.

Kick back relax and experience the best of two worlds, the luxury and comfort of a 5 star hotel and the warmth and peace of feeling right at home. This stylish space offers a variety of books to read and a wonderful jet tub to enjoy after a long trip or day at work; along with clean and cozy beds. Take advantage of our welcome coffee bar with a nice selection of teas and snacks exclusive for our guest.

Family · Location · Amenities