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Holiday rentals in Cherry Valley

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Top-rated holiday rentals in Cherry Valley

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
4.91 out of 5 average rating, 94 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+!

Guest favourite
An inviting living area features a deep blue sofa and two gray armchairs arranged on a patterned rug. A low coffee table sits in front, while a large TV is mounted on the exposed brick wall. Natural light flows through the skylight above.
Loft in Rockford
4.94 out of 5 average rating, 156 reviews

Franklin's Urban Retreat in the heart of downtown

Live the urban city life in this centrally located loft designed with tons of local art and custom built furnishings. Our loft of is an open floor plan with tall exposed ceilings and brick. Have fun playing our full size retro Arcade and slot machine. And when ready to sleep, you are gonna LOVE the Saatva mattress. Located right in the middle of all the downtown action surrounded by the best restaurants and activities. Located above Abreo Restaurant, all guests receive 10% discount during stay

Guest favourite
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
4.94 out of 5 average rating, 96 reviews

Victorian*4 poster King*Walk to village*A+ Kitchen

✔︎ 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

Guest favourite
A dining area features a wooden table surrounded by six light-toned chairs. Natural light enters through sliding glass doors, which lead to a patio. A small side table holds a decorative item, and a painting hangs on the wall, adding visual interest.
Flat in Rockford
4.84 out of 5 average rating, 136 reviews

Splash of Swedish in an Exposed Basement Apartment

Nestled in a family friendly neighborhood, this lower unit with private entrance, offers a quiet stay with friendly neighbors. Fast Wi-Fi and Television with a Peacock subscription are provided. Located near highway 20 offers easy access to the airport and highways 39 and 90. The home is 4 min away from Atwood Park, providing miles of scenic hiking and a rescued bird aviary. A 13 min drive gets you to downtown Rockford with numerous shops, museums, restaurants and views of the Rock River.

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, 439 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 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, 139 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
A comfortable seating area features two black reclining sofas positioned around a glass coffee table. A lamp beside the sofa provides soft lighting, while a world map artwork adds a touch of decor to the neutral-toned walls.
Flat in Byron
4.98 out of 5 average rating, 101 reviews

Location-dining, golf, brewery, parks. We have it

The Loft is an upstairs apartment just a few blocks from downtown Byron, IL and near many local attractions and recreational places/activities. Completely renovated and updated. Clean, bright, and well appointed. This unit has two bedrooms - 1 with a king bed and 1 with a queen bed. There is 1 bathroom with a shower only. There is a washer and dryer in the unit. Please note this unit is on the second floor - with an inside and outside staircase. This property has central heat and air.

Top guest favourite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Flat in Aurora
4.98 out of 5 average rating, 245 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Top guest favourite
A charming brick building, enveloped by lush greenery, features a welcoming entrance with a secure door. Large windows framed by ivy provide warmth to the facade. Flower beds with colorful plants offer a touch of vibrancy along the pathway leading to the front door.
Flat in Edgewater
4.96 out of 5 average rating, 189 reviews

Upscale Urban Retreat 1 Bedroom Apt. 2nd floor

Charm Art Style. Hardwood floors, original woodwork. Secure keypad entry. Spacious cozy apartment with full kitchen and dining room. Owner on adjoining premises. Street parking. Minutes to Sports Factory, downtown nightlife, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory & Sinnissippi Gardens. 5 blocks to river and rec path. Quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. Not suitable for children under 6.

Top guest favourite
The exterior of the bungalow features a welcoming, brick facade with a sloped roof and a prominent front porch. Large windows allow natural light inside, while colorful flowers in the front garden add charm to the entrance.
Bungalow in Rockford
4.96 out of 5 average rating, 454 reviews

Arts and Crafts Bungalow with Outdoor Space

We welcome you to a centrally located two-bedroom Arts & Crafts Bungalow. Ideally situated near sports venues, shopping, museums, and restaurants, the house is a perfect place for families, professionals, and couples. We have free on street parking in front of the home, We are 10 minutes away from the UW Sports Factory, Anderson Japanese Gardens, and Nicholas Conservatory. We are 20 minutes away from Anna Page Park and Rock Cut State Park.

Top 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
4.95 out of 5 average rating, 242 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!

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, 140 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.

Popular amenities for Cherry Valley holiday rentals