Holiday rentals in Leaf River

GOOSE ISLAND CABIN -Secluded Riverside Eco-Retreat

Nestled along the banks of the Rock River under tall oaks, ye ol cabin was built by early settlers in 1907. Legit rustic charm. Secluded yet only 10 mins from town. 100 acres of private property, bordering Lowden-Miller State Forest. Includes canoes/kayaks, large riverfront yard, grills, hammocks, porch and firewood. $33/night per person or pet after the first 2 ppl, incl. visitors. 3 night minimum w/ Fri or Sat. 2 night min. for Sun-Thurs. Msg Tim for larger groups & events. Closed for winter.

Location · Value · Accuracy

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.

Value · Location · Indoor spaces

Gorgeous Sprawling Acreage w/ Stunning Views

Soak up the sprawling valley views from the wrap around front porch in this beautiful farmhouse. From the moment you arrive, the calm, peaceful location will melt away stress. Sit by the fire pit, enjoy private walking trails on the property, or just sit on the porch and take it all in. Just a few miles from everything including grocery stores, restaurants, shopping, golf, bowling, wedding venues, bison, entertainment and more. Ample parking for trailers. Hunting on property is not allowed.

Family · Location · Kitchen

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.

Value · Location · Comfort

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.

Value · Location · Condition

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.

Family · Location · Walkability

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.

Family · Value · Quiet

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

Location · Value · Biking

Historic Cottage Walk to Downtown & Trails

Step into a restored 1875 Victorian cottage just a short walk from downtown Oregon, IL. Thoughtfully decorated to create a warm, inviting escape with vintage charm. Relax on the porch, explore nearby nature, or enjoy local restaurants, a brewery, shops, and scenic views. Ideal for couples, solo travelers, small groups, and those visiting for work or longer stays near Woods, Etnyre, the Byron plant, and KSB Hospital. Also used as a filming location for multiple productions.

Location · Value · Indoor spaces

Ann's Place

Enjoy a cozy and clean relaxing visit at, "Ann's Place!" Fully refreshed this year with new amenities, linens, bedding inside and outside. The outside has great off street parking along with a sitting area. Enjoy the quiet neighborhood or a stroll down to the river. The Rock River is located two blocks from Ann's Place along with a playground for littles to run. Hairy Cow Brewing is located along the Rock River and just a 5 minute walk from Ann's Place. No pets allowed.

Location · Value · Comfort

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!

Family · Value · Indoor spaces

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 · Value · Laundry