Vacation rentals in Cherry Valley

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Top-rated vacation rentals in Cherry Valley

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

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Guest favorite
A golf simulator room is equipped with a large screen displaying a scenic golf course. A golf bag and clubs are positioned nearby on a green carpet, with practice balls scattered in front of the tee area. Dark curtains frame the windows, and walls feature decorative artwork.
Home in Rockford
4.98 out of 5 average rating, 104 reviews

Golf Simulator • Hot Tub • Arcade • Massage Room

Welcome to the Golfer's Retreat & Arcade, where relaxation & excitement await! Indulge in a few rounds on our golf simulator, perfect for honing your skills or simply enjoying a friendly competition. Then, treat yourself to some well-deserved rest & rejuvenation in our massage chairs, melting away the stress of the day. Immerse yourself in the free-play arcade, where endless entertainment awaits. Get ready for an unforgettable experience for the whole family. Pet fee $50/night per dog-max 2 dogs

Guest favorite
The exterior of a charming Barndominium is showcased, featuring a neutral color palette with a metal roof. The building displays large windows and a large garage door. Flower planters line the entrance, and well-maintained grass surrounds the structure, enhancing the rural ambiance.
Barn in Clare
4.93 out of 5 average rating, 116 reviews

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.

Top guest favorite
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
4.93 out of 5 average rating, 107 reviews

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

Guest favorite
An A-frame structure is nestled among lush green trees, showcasing large glass windows that allow for ample natural light. The contrasting wood siding complements the surrounding foliage, creating a harmonious blend with nature. A raised deck leads to the entrance, enhancing accessibility to the home.
Cabin in Fontana-on-Geneva Lake
4.93 out of 5 average rating, 188 reviews

Exquisite Modern A-frame all WithInnReach

An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

Top guest favorite
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.
Apartment in Cherry Valley
4.97 out of 5 average rating, 475 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.

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.
Home in Rockford
4.91 out of 5 average rating, 122 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

Top guest favorite
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.
Apartment in Rockford
4.95 out of 5 average rating, 224 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.

Guest favorite
An outdoor patio area is shown, featuring a large red umbrella providing shade over a dining table with matching red chairs. A grill is positioned nearby, with a view of lush greenery and a water feature in the background, offering a peaceful setting for outdoor gatherings.
Home in Cherry Valley
4.83 out of 5 average rating, 108 reviews

CherryValley Cabin|Hot Tub+Sauna+Scenic Riverfront

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.

Top guest favorite
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.
Apartment in Rockford
4.99 out of 5 average rating, 103 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 favorite
The front of a cape cod style home is shown, featuring a welcoming porch with white railings and hanging flower baskets. The house is surrounded by well-maintained green grass and lush shrubs, with two gabled dormers on the roof adding character.
Home in Rockford
4.98 out of 5 average rating, 241 reviews

Business access in residential comfort

Clean, convenient, cozy cape cod style home in quiet neighborhood with fenced back yard. Just minutes drive to highways 20, 39, I90, downtown Rockford, & SportsCore. I'm willing to adjust check-in/out times if I can, just ask. Message me if you have any questions, or would like to request a long term stay. It is a really pleasant home! Per Airbnb rules, please do not book for someone else. Garage space is available for a fee, please inquire at booking.

Top guest favorite
The Spanish-style villa is framed by lush greenery and a landscaped garden featuring stone pathways. Distinctive red windows and subtle lighting enhance the exterior's charm. The upper level is visible, showcasing a unique architectural design that complements the overall aesthetic.
Home in Rockford
4.99 out of 5 average rating, 341 reviews

Hidden Gem Spanish Style Villa

Unique to Northern Illinois, this Spanish style Villa sleeps 10+ , boasts five patios, a Cantina, 7 ARCADES, HOT TUB, and many surprises you will find as you look at every turn to something unexpected. This property is filled with beautiful furnishings, featuring a balcony off of the upper level that boasts a 12 foot ceiling. Everything from two walk in showers, a jet tub and a hot tub for any level of self-care desired.

Top guest favorite
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, 253 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!

Popular amenities for Cherry Valley vacation rentals