
House holiday rentals in Cherry Valley
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Top-rated house rentals in Cherry Valley
Guests agree: these houses are highly rated for location, cleanliness and more.

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
4.98 out of 5 average rating, 105 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.
4.95 out of 5 average rating, 116 reviews
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!
4.97 out of 5 average rating, 141 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
4.94 out of 5 average rating, 109 reviews
Pets-Sleeps 7- Event Room Rochelle
Super Clean, Quiet & Cozy! 🐕Pet friendly 🙂Event Room Available -Ask!! (Additional fee ) 90 mi to Chicago! 2 hrs to the Dells! 5 min west of Hwy 39/51 15 min to NIU 45 min to Rockford Walking and bike trail nearby! Beautiful home! Super clean! Monday-Sat check: 3 PM Sunday Check-In: 5 PM Our eight-jet power shower will relax those tired muscles after a full day of activity. A soak in our modern,free-standing tub will sooth and your worries away. A well stocked kitchen awaits you!
4.96 out of 5 average rating, 156 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.
5.0 out of 5 average rating, 155 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
4.91 out of 5 average rating, 127 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.
4.97 out of 5 average rating, 117 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!!
4.96 out of 5 average rating, 114 reviews
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.
4.83 out of 5 average rating, 109 reviews
Your home away from home
Fully remodeled 1940's Cape Cod style house with entertainment, office and sun room. Conveniently located in the heart of Rockford this stylish home is close to shops, restaurants and downtown attractions. It has three bedrooms and two full bathrooms, with an desk in the bedroom of the first floor. The high speed wifi internet, roku ultra and xbox console can make your stay even more enjoyable. Be your own chef in the fully equipped kitchen with new appliances
4.95 out of 5 average rating, 115 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.
4.98 out of 5 average rating, 245 reviewsPopular amenities for house rentals in Cherry Valley
House rentals with a pool

Grand 1800s Victorian Gem: Updated/by Downtown
4.9 out of 5 average rating, 101 reviews
Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD
4.95 out of 5 average rating, 122 reviews
Home away from Home
4.93 out of 5 average rating, 174 reviews
Cozy cabin getaway near Lake Como and Lake Geneva
4.98 out of 5 average rating, 49 reviews
Skip & Reed's River Retreat
5.0 out of 5 average rating, 53 reviews
Treetop Lakehouse at Abbey Springs
5.0 out of 5 average rating, 16 reviews
Lake Geneva Home w/ Pool near the Lake!
5.0 out of 5 average rating, 26 reviews
Geneva Grove | Pool, Dog Friendly, Sleeps 8
4.91 out of 5 average rating, 23 reviewsWeekly house rentals

Sanctuary Woodland Guest House!
4.95 out of 5 average rating, 219 reviews
Charming 1930s "Kinsey Farms" Cottage
4.92 out of 5 average rating, 112 reviews
Country charmer 1885 vintage farmhouse near NIU
4.91 out of 5 average rating, 274 reviews
The Main Event Game House on the Huntley Square!
4.96 out of 5 average rating, 184 reviews
Cozy Cottage Oasis in Charming Grand Detour
4.74 out of 5 average rating, 176 reviews
Luxury & Comfort in a Large Home
4.8 out of 5 average rating, 15 reviews
Phoenix House | Firepit & Big Backyard TV Room
4.84 out of 5 average rating, 68 reviews
Beautiful 3 Bedroom 2 bath home in Loves Park
4.95 out of 5 average rating, 38 reviewsPrivate house rentals

Spacious 3BR w/ Game Room, yard, central Rockford
4.93 out of 5 average rating, 27 reviews
Spacious family home, Hot tub
5.0 out of 5 average rating, 19 reviews
Storybook Stay by the River and Gardens
4.96 out of 5 average rating, 24 reviews
Steps from RockRiver•Massage Chair•Arcade•Firepit
4.99 out of 5 average rating, 69 reviews
Game Room with a 4 Bedroom House
4.67 out of 5 average rating, 227 reviews
Designer Home - King Suite, Game Room, Hot Tub
5.0 out of 5 average rating, 23 reviews
Spacious & charming home. Centrally located.
5.0 out of 5 average rating, 55 reviews
Charming Pet-Friendly Rockford Escape
5.0 out of 5 average rating, 68 reviewsDestinations to explore
- Chicago Holiday rentals
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- Alpine Valley Resort
- Wilmot Mountain Ski Resort
- Lake Geneva Public Library
- Lake Geneva Cruise Line
- Chicago Premium Outlets
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Alpine Valley Music Theatre
- Cantighy Park
- Rock Cut State Park
- Big Foot Beach State Park
- Discovery Center Museum
- Nicholas Conservatory And Gardens
- Lake Geneva Ziplines & Adventures





