House holiday rentals in Machesney Park

A stately three-story brick home is displayed, showcasing a spacious patio area with a mixture of shaded and sunny spots. Lush green grass surrounds the property, with well-maintained landscaping complementing the structure. Large windows provide ample natural light, highlighting the inviting outdoor space.

4.95 out of 5 average rating, 116 reviews

Historical Riverfront Mansion: Serenity+Location

This house was built in 1916 and has recently been beautifully renovated. This property was once considered one of Rockford's Mansions because of its large accommodating 3 story size. Come enter the tranquility that this property provides from its riverside views to its endless entertainment possibilities. The moment you drive through the gates and down the tree lined driveway; you know that you have been transferred to a private retreat where you can relax from the city. Inquire for 10+ guests.

4.97 out of 5 average rating, 142 reviews

A cozy living room is depicted with a gray sofa and a wooden coffee table resting on a patterned area rug. Natural light fills the space through large windows, highlighting the warm wood trim and the adjacent dining area featuring a wooden table and chairs.

Home in South Beloit

Beautiful Craftsman Style Home w/ Fenced Yard

Enjoy your stay in this beautifully remodeled Craftsman Style Home. Rich with the character of an abundance of wood trim and paneled ceilings, this home is the perfect place for a relaxed, stress free, memorable stay. Complimentary coffee, tea, and bottled water are included. Other amenities include a bike path, private parking, a fenced yard, use of a grill and laundry. Less than a mile away from the revitalized city of Beloit WI, you will have many options for places to eat and things to do!

4.94 out of 5 average rating, 109 reviews

The exterior of a charming two-story house is presented, featuring blue siding and a welcoming front porch. Lush green grass surrounds the home, with flower beds adding a touch of color. The neighboring trees and vintage street lamp create a peaceful, suburban atmosphere.

Home in Cherry Valley

BoutiqueVictorian*FamilyFriendly*VillageEats&Parks

✔︎ Family friendly ✔︎ Fenced yard ✔︎ Generously equipped kitchen ★ "Everything you need and then some is within easy walking distance." ★ "The beds were comfy and there were thoughtful amenities throughout.” ➢ 1 min walk to restaurants, parks, bars, coffee, ice cream, mini grocery store & more ➢ Quiet neighborhood ➢ Onsite washer & dryer ➢ Piano & acoustic guitar ➢ DVDs & games ➢ Grill & outdoor dining ➢ Family owned and managed by longtime village residents ➢ Attentive and friendly hosts

A comfortable living room features a pair of brown leather sofas and a wooden coffee table, arranged over a light rug. A wall-mounted TV displays a scenic image. Natural light filters through the nearby windows, illuminating the space with a warm glow.

4.93 out of 5 average rating, 136 reviews

Downtown Fun, 2 Doors from River

Historic home with modern amenities by the river & downtown Rockford. 3 bedrooms, 2.5 bathrooms, pool table gameroom, computer workspace, full kitchen. Ride our beach cruiser along the breathtaking Rock River Bike Path to top attractions including Anderson Japanese Garden, Discovery Center Museum, Burpee Museum, Sinnissippi Riverfront Park—all within 5 minutes. At day end, unwind and entertain your family in the playroom with pool table and big screen TV. Book now to lock in your next getaway!

4.99 out of 5 average rating, 326 reviews

A small outdoor deck features a round red table accompanied by two matching chairs. Lush greenery and hanging plants adorn the area, providing a serene view of the wooded backyard. The soft illumination adds a cozy touch, inviting relaxation.

Home in Roscoe

* Travelers Sanctuary 2bed 2bath unit-sf home

Two bedroom, two bath entire first-floor of a single family home. 1350 sq ft. Self check-in. Central Air. Parking in driveway. Host lives in lower unit, separate entrance. 1-acre, wooded backyard. 4 mi to I90/39-Exit Rockton Rd. 11 mi N of Rockford 7-8 minute drive to forest preserves, grocery. Ideal for biz class guests, couples. Safety issues for children under 8 years. Share a bit about yourself, why in the area, who you are traveling with & that you read & agree to "House Rules".

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.

5.0 out of 5 average rating, 155 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.

Superhost

A warm living area showcases rich wooden accents, featuring a cozy leather sofa and a classic armchair. A coffee table sits at the center with a decorative item. A fireplace is highlighted with a framed art piece above, surrounded by natural light from multiple windows.

4.91 out of 5 average rating, 127 reviews

beautifully restored bungalow | 2 queen beds

Our meticulously restored bungalow blends historic charm with modern comfort. If you love the character of older urban neighborhoods, you'll feel right at home here. If you prefer a newer suburban setting, our home may not be the best fit. Enjoy a cup of pour-over coffee, then curl up with a good book from our curated library. This gem features: • Fenced yard • Modern kitchen • Tranquil bedrooms • Pour-over coffee supplies • Luxurious bathroom • Cozy, thoughtfully designed interiors

4.97 out of 5 average rating, 117 reviews

Home in Rockton

HD Jameson House at River’s Edge

Nestled on the Rock River, the HD Jameson House, a National Historic Register gem, blends historic charm with modern amenities. Enjoy river views and with quaint shops and restaurants exploring the Village of Rockton is a perfect family-friendly retreat. This haven is surrounded by nature but close to numerous attritions, ideal for a romantic getaway or peaceful escape. The HD Jameson House offers a heavenly retreat, blending past beauty with present allure for everyone in the family.

4.96 out of 5 average rating, 114 reviews

Mid-Term Ready | 4BR Home, Fast WiFi, Pet-Friendly

Looking for a far away vacation? Or how about a home right next to home? Welcome to our Rockford AirBnB! Even Chicago is within reach when you stay- busses route between Rockford and Chicago every few hours. Shop at Cherry Valley Mall, explore and dream with the koi at Anderson’s Japanese Gardens, get water thrills at Hurricane Harbor Rockford, or even take a nature expedition at Rock Cut State Park! All within 10 miles or less! “Book instantly now and guarantee your stay!!

An outdoor pool area is surrounded by a well-maintained patio and wooden fencing. The clear blue water of the pool contrasts with the beige pavers, while a shaded gazebo provides seating nearby for relaxation. Lush greenery enhances the tranquil atmosphere.

4.95 out of 5 average rating, 106 reviews

Pool, Arcade, Hot Tub and more @16th and Aldeen

Do you want to be the Hero? Hero spouse, hero golf buddy, even Guitar hero?! You can be that and more at our hole-in-one nestled at the end of a quiet street right by a top 50 rated public golf course. Get in a round then head back to the hot tub to soothe that putting shoulder while the kids play in the pool. Then head inside to the arcade to play guitar hero till you win that Grammy you always wanted. Top it off with a family movie night! Pet fee $50/night per dog max 2 dogs

4.83 out of 5 average rating, 109 reviews

Home in Cherry Valley

Log Cabin Retreat With Hot Tub & Sauna

Welcome to your perfect getaway! Our house is ideal for couples, families, or small groups looking to escape the hustle and bustle of daily life and reconnect with nature. ★ Relax in Hot Tub ★ Rest in Sauna ★ Sleep - 3 Bedrooms, 5 beds ★ Gather around fire pit with family and friends ★ Rest peacefully in a 3 king-size beds ★ Watch your favorite shows on 4 Roku TV’s around house ★ Stay connected with fast Wi-Fi. ★ Play foosball tournaments ★ Hiking, fishing, kayaking.

A bright living room features a light-colored sofa and a matching loveseat facing a dark wooden coffee table. A patterned red area rug covers the hardwood floor, while natural light filters through a window with white blinds. Artwork adorns the walls, adding a touch of color.