
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.

Hip-N-Colorful Prospect Smoke Free
Excited to offer this space to travelers! We have fun with some color. Queen bed in the first bedroom, XL twin beds in the back bedroom. Great location! Close to stylish, revitalized downtown Rockford with terrific restaurants, night life, shops, and galleries. Upper unit in vintage 4 family with long term tenants below and I live in the other upper. Absolutely no parties. Only registered guests. No smoking inside or outside on the property. Violation results in $500 cleaning fee/poor review

Charming Boulevard Home Near Downtown & Hospitals
Three Bedroom Brick home with fireplace and outdoor space located in neighborhood along a favorite route for runners/cyclists. 3-6 minutes from Anderson Gardens, UW Sports Factory, Coronado Theater and downtown events. Close to all hospitals and a quick and easy drive to both Sportscores. Second floor bedrooms with dressers and closets. Two have view of river. Kitchen is well stocked for easy meal preparation. Cozy backyard is fenced with brick patio, grill and table. Discounts for Week/Month.

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

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.

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.

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.

Historic Randall Schoolhouse
You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Look at the reviews! Julie's House on Main
Super Clean, Quiet and Cozy! Pet friendly... 🐾 🐕 ❤ 🐶 (Applicant + Fee required) 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!

Fun Retro Apartment in Downtown Rockford
Close to all the action, you are steps away from top restaurants, night life, theaters, sports and the river. Freshly updated space with an extra touch of all things we love 80's, you will find an Atari 5200 with favorites like Pac Man along with your favorite VHS tapes like Breakfast Club and Sixteen Candles. We have a dedicated work area in second bedroom. Great for a quick trip or long work stay. Located steps from Abreo Restaurant, all guests receive 10% discount during stay

Stylish 1854 Artist’s Qtrs: Walk to Sports Factory
Creativity - - that elusive, mysterious talent we all admire. Years ago, the Artist’s Quarters was the creative think tank of just such a genius. For decades the rooms were filled with the artist’s works, thoughts and borderline crazy energy. Now, the New Artist’s Quarters has become a re-imagining of the creative genius’s studio. It’s an environment designed for you, filled with art and objects that will inspire your creative soul. Recharge yourself in our Artist’s Quarters.

Cherry Valley Catch & Cozy
Take it easy at this unique and tranquil getaway. Enjoy cooking on a 1900’s six-burner stove. 5 minutes away from The Hard Rock Casino, The Cherry Valley Mall, and Six Flags Hurricane Harbor. Enjoy the Anderson Japanese Gardens or take a hike at the Rock Cut State Park or enjoy a 3 minute walk to Bowman Park. Enjoy taking a stroll through the Espenscheid Forest Preserves. If you don’t feel like going out, stay in and fish all day, grill on the patio. Welcome to Cherry Valley!

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.
Popular amenities for Cherry Valley holiday rentals
Other great holiday rentals in Cherry Valley

Cozy townhome secluded in City

The Gilded Cottage- 3BDM, Newly Renovated

Updated house-great south Rockford neighborhood!

Charming Cottage!

Ranch Style w/ firepit & big backyard TV Room

Lakeside Tiny House Farm Retreat

Biz Class Apt w Conf Room

Victor Victorian
Destinations to explore
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- Alpine Valley Resort
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- Rock Cut State Park
- White Pines Forest State Park
- Richard Bong State Recreation Area
- Medinah Country Club
- Villa Olivia
- Hurricane Harbor Rockford
- Moraine Hills State Park
- Black Sheep Golf Club
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Otter Cove Aquatic Park
- The Water Works Indoor Water Park
- Lynfred Winery
- Fox Valley Winery Inc
- Staller Estate Winery
- Valentino Vineyards & Winery
- DC Estate Winery




