Holiday rentals in Leaf River

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Top-rated holiday rentals in Leaf River

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

A cozy living room features a light grey sofa and a wooden table. A television is positioned on a stand, and a patterned area rug complements the space. The open layout allows for a view into the adjacent kitchen area, with natural light illuminating the room.

Home in Rockford

4.92 out of 5 average rating, 107 reviews

Charming 1930s "Kinsey Farms" Cottage

Your family will be close to everything when you stay at this centrally-located place. Easy highway access and less than 10 minutes from downtown - all the fun Rockford has to offer! Located on a quiet, dead end street. Walk to the playground at Ken-Rock park! Several stores/restaurants nearby. One hour drive to Chicago O'Hare airport, and only 3 miles from Rockford Intl Airport. Lots of recreation in the area including Rock Cut State Park, Anderson Japanese Gardens, and Klehm Arboretum. LGBTQ+!

LocationFamilyHiking

Top guest favourite

The cabin's spacious deck is surrounded by tall trees, with warm light strung above creating a welcoming ambiance. A peaceful view of the Rock River is visible through the trees, inviting relaxation in a serene outdoor setting.

Cabin in Oregon

4.96 out of 5 average rating, 204 reviews

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.

ValueLocationNearby

Top guest favourite

A fire pit is surrounded by two red Adirondack chairs, positioned on a grassy area. A stack of logs serves as a rustic bench. In the background, a red barn with solar panels is visible, complemented by trees and fields beyond.

Home in Oregon

4.97 out of 5 average rating, 33 reviews

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.

LocationFamilyOutdoor spaces

Top guest favourite

Cabin in Elizabeth

4.98 out of 5 average rating, 132 reviews

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.

FamilyLocationSleep quality

Top guest favourite

A hot tub is positioned on a deck overlooking a scenic river view. The water's surface reflects soft light, creating a serene ambiance. A lattice privacy screen is visible in the background, framing the peaceful outdoor setting.

Home in Rockford

5 out of 5 average rating, 149 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.

LocationValueView

Top guest favourite

A spacious outdoor area features a fire pit surrounded by seating. In the background, a large barn with a green and white exterior is visible, set against a serene landscape of lush grass and trees.

Flat in Cherry Valley

4.97 out of 5 average rating, 469 reviews

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.

ValueLocationBack garden

Top guest favourite

Home in Oregon

5 out of 5 average rating, 67 reviews

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.

ValueFamilyParking

Guest favourite

A cozy living area is furnished with a spacious bed and a sleek desk next to a decorative chair. A modern light fixture hangs from the ceiling, illuminating the space. A small kitchenette with a refrigerator and microwave is visible, along with a doorway leading to a bathroom.

Guest house in Rockford

4.79 out of 5 average rating, 29 reviews

1 Cozy and peaceful place

Kick back and relax in this calm, stylish space. Perfect place to relax after work. This is a guest small duplex house semi-attached to the main home. We are located near the Lowes Distribution Center, the Chicago-Rockford International Airport, about 20-minute drive to the Byron Plant, and about 6-to-8-minute drive to downtown Rockford, Discovery Center, Coronado Theatre, BMO Center, and about 12 minutes away from Swedish American Hospital.

ValueLocationQuiet

Top guest favourite

The welcoming front porch features a cozy table and two chairs set on a wooden deck. A hanging flower basket adds a touch of color. The surrounding area is landscaped with green plants and flowers, creating a pleasant entryway to the home.

Cottage in Winnebago

4.95 out of 5 average rating, 78 reviews

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.

ValueFamilyAmenities

Top guest favourite

The entrance to Shelby's cottage features a warm wooden door framed by decorative wreaths. A sign reading 'Shelby’s Garden' is mounted on the wall, accompanied by greenery and a light fixture. Holiday lights add a festive touch to the exterior.

Guest house in Rockford

4.96 out of 5 average rating, 47 reviews

Shelby’s garden cottage.

Shelby’s cottage has been part of Bluffs on the bend farm for over 65 years. It has undergone a complete overhaul and update with all the modern conveniences while retaining a country cottage charm. It is the perfect getaway for a couple. The location is next to the historic ( originated in 1924 ) Kilbuck Bluffs Forest Preserve. While being nestled in the country it is centrally located to restaurants , bars and shopping.

FamilyLocationOutdoor spaces

Guest favourite

A sunlit room features large windows that offer views of the surrounding landscape, including the river. A sectional couch and an ottoman provide comfortable seating, while a television is positioned nearby. The space is adorned with wooden walls and a ceiling that adds warmth to the atmosphere.

Cabin in Oregon

4.96 out of 5 average rating, 251 reviews

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!

ValueLocationRiver

Top guest favourite

A warm living area is showcased with a large bookshelf filled with a variety of books. Comfortable seating, including two armchairs and a sofa, surrounds a decorative area rug. A cozy fireplace is centered beneath a wall-mounted television, while a Christmas tree adds a festive touch near the window.

Home in Rockford

5 out of 5 average rating, 174 reviews

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.

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