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Holiday rentals in Machesney Park

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Top-rated holiday rentals in Machesney Park

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

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Top guest favourite
The exterior of the countryside cottage is displayed, featuring a charming facade with light gray siding and a welcoming sign. Lush green grass surrounds the home, complemented by landscaped garden beds filled with blooming bushes. A cozy porch is visible, with seating arrangements enhancing outdoor leisure.
Cottage in Rockton
4.97 out of 5 average rating, 265 reviews

Country Farm Cottage

Cozy farmhouse Country Cottage on a historic private farm setting. Safe, quiet, peaceful space to relax. Minutes to golfing, hiking, antiques, canoeing, camping, parks, or use as writers retreat. Rockton has great shopping & dining, 20 min to trendy eateries in Beloit WI. Close to local wedding venues Wineries 25 min away May- Nov: orchards cider & donuts Child friendly Visit our Goats Wifi & Roku TVs No Smoking inside No Pets Farm animals and pets on the farm Host lives on same farmstead

Guest favourite
A modern kitchen is featured, equipped with stainless steel appliances and a large granite island with seating for several. A dining area is visible, furnished with a wooden table and black chairs. Natural light filters in through a window adorned with light curtains.
Apartment in Loves Park
4.94 out of 5 average rating, 48 reviews

Awesome 3 Bedroom 2 bath condo!

Relax with the whole family at this peaceful place to stay! This brand new unit offers 3 bedrooms and 2 full baths with a walk-out basement and a deck off of the dining room! Rock Cut State Park is 3.7 mi away. Major shopping is 3.5 mi away. Enjoy a hike in Rock Cut State Park, a walk through Anderson Japanese Gardens, take the kids to Six Flags-Hurricane Harbor, try your luck at the Hard Rock Casino or just sit on the back deck and enjoy the view! Please note: we have other units available

Top guest favourite
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
4.99 out of 5 average rating, 319 reviews

* 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".

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.
Farm stay in Cherry Valley
4.97 out of 5 average rating, 425 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.

Top guest favourite
A striking bedroom features a four-poster bed adorned with red sheets and an illuminated sign that reads 'TRUST ME LOVE ME.' Mirrors are positioned on the wall, reflecting the ambient red lighting, creating an intimate atmosphere within the space.
Home in Rockford
5 out of 5 average rating, 131 reviews

Adults Only "Red Room" Home with Hot Tub

Unique adult themed home with a BDSM / "Red Room" experience. It's a great way for couples to turn their fantasies into reality and explore with each other. Includes St Andrews Cross, Swing, and Sybian! Relax on the patio or in the hot tub with a scenic view of the Rock River. Once you arrive you will not want to leave so we try to provide you with everything you may need for your stay! Frozen pizzas, Bottled Water, Coffee, Robes, Firewood and a special gift with each reservation.

Top guest favourite
Home in Rockton
4.97 out of 5 average rating, 102 reviews

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.

Superhost
The game room features a variety of entertainment options, including a ping pong table, a foosball table, and a Skee-Ball machine. Ambient lighting elements enhance the playful atmosphere. Comfortable seating is available in the form of a cozy chair, with an area rug adding a touch of warmth.
Home in Rockford
4.8 out of 5 average rating, 211 reviews

Spacious Cabin-style home w/ Gameroom + Gym!

Welcome to our spacious, yet cozy cabin-style retreat, perfect for both relaxation & entertainment! Enjoy the large yet inviting living room, savor homemade meals in our fully-equipped kitchen, complete with modern appliances. Unleash your inner gamer in our epic Game Room or let the kids explore a world of fun in the dedicated play area. Stay fit on-the-go in our well-equipped home gym, stocked with top-notch equipment. Need to work? Enjoy our dedicated workstation for seamless focus.

Top guest favourite
The cottage features a charming facade with a combination of blue siding and stonework. Two sets of double doors are framed by large windows, allowing natural light to fill the entrance. Flower beds line the pathway leading to the front door, enhancing the welcoming appearance.
Home in Elkhorn
4.97 out of 5 average rating, 146 reviews

Cozy Country Cottage near Lake Geneva, WI

Our Cozy Cottage features 3 comfortable bedrooms and nightly magnificent sunsets. Nestled on a country road, the house offers plenty of space to rest after visiting Lake Geneva, Lauderdale lakes, biking at Kettle Moraine or site seeing in the area. It’s close to Walworth County fair grounds where the flea market, Das Fest and Rib Fest are held. This is country living with plenty of opportunity to enjoy the beautiful outdoors or the peace and quiet of the countryside.

Top guest favourite
A spacious family room is illuminated by natural light from large windows. Comfortable seating includes a sectional couch and armchair, while a coffee table sits atop a decorative area rug. A large flat-screen TV is mounted on the wall, and access to the private deck is visible.
Flat in Rockford
4.99 out of 5 average rating, 84 reviews

Charming Ranch-Style Apartment. Modern Amenities

Welcome to your perfect home away from home, the Gem of Sandra Lane. Whether you're here for a family vacation or a business trip, this apartment has everything you need to feel at ease. Relax in the large family room or private deck and sleep tight on the king-sized bed in the master bedroom. This apartment also features a beautiful kitchen with brand new Kitchen-Aid appliances. It also offers easy access to all of Rockford's top attractions, dining, and shopping.

Top guest favourite
The exterior of a two-story brick building is depicted, adorned with climbing ivy and surrounded by lush greenery. The entrance features a central doorway framed by windows, with a welcoming pathway leading from the sidewalk to the door.
Flat in Edgewater
4.93 out of 5 average rating, 597 reviews

Upscale Urban Retreat 1 bedroom, ground Floor

Charming and beautiful ground floor; wood floors and original woodwork. Secure keypad entry. Owner on adjoining premises. Minutes to Indoor Sports Factory, downtown nightlife, restaurants, shops, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory and Sinnissippi Gardens.. 5 blocks to river and rec path. Centrally located quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. High speed internet.

Guest favourite
A floor plan of the home is displayed, showcasing two bedrooms, a living room with a sofa sleeper, and a modern kitchen. An outdoor living space is indicated on the right side. Distinct areas for dining and a small office space are also visible.
Cottage in Machesney Park
4.95 out of 5 average rating, 75 reviews

Charming Cottage!

Freshly & fully modern retreat offers far more comfort and style than any hotel. It’s the perfect home base, a cozy haven for short-term “between homes” stays, and an ideal launchpad with easy I-90 access. You’ll be close to shopping, dining, medical facilities, and just minutes everything fun!. Inside, you’ll find 2 welcoming bedrooms—a queen bed & a full-sized bed. Outside, a stunning new living space awaits, offering unmatched ambiance for relaxation.

Guest favourite
A cozy cabin interior features warm wooden paneling and soft lighting. A brick fireplace adds comfort, while a spacious bed is dressed in a patterned quilt. A inviting sofa and round area rugs enhance the welcoming atmosphere of the living space.
Cabin in Brodhead
4.86 out of 5 average rating, 153 reviews

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!

Popular amenities for Machesney Park holiday rentals