Holiday rentals in Cherry Valley

Find and book unique accommodation on Airbnb

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

Cottage in Rockton

4.95 out of 5 average rating, 188 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

26 Dec – 2 Jan

$236 SGD per night

Guest favourite

Barn in Rockford

4.98 out of 5 average rating, 173 reviews

Charming converted barn north of Rockford, Ill

We'll be delighted to welcome you to our converted barn. Most describe it as "charming." We are grateful for those comments, and we have tried to provide our guests with a safe, restful, and inviting environment. There are two bedrooms upstairs, and a TV room with 2 twin beds/daybeds downstairs. The galley kitchen has brand new appliances. The beds are outfitted with the most healthful, hygienic mattress pads and bedding we could find. The water is certified free of lead, nitrates, or bacteria.

20–27 Oct

$192 SGD per night

Guest favourite

Farm stay in Caledonia

4.89 out of 5 average rating, 104 reviews

Country Guesthouse at Wind Ridge Herb Farm

Welcome to Wind Ridge Herb Farm. Enjoy the peace and tranquility of this beautiful historic, Victorian farm. Just minutes from Rockford, Machesney Park and Beloit, the guesthouse is ideal for couples, friends, families or professionals seeking safe, private and quiet accommodations. Conveniently located near I90, Pierce Lake and Rock Cut State Park, great golf courses and biking, restaurants and shopping, Anderson Japanese Gardens, Nicholas Conservatory and Hard Rock Casino are all nearby.

28 Sep – 5 Oct

$191 SGD per night

Guest favourite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 274 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.

25 Aug – 1 Sep

$134 SGD per night

Guest favourite

Home in Rockford

4.98 out of 5 average rating, 256 reviews

Hidden Gem Spanish Style Villa

Ask about our special, Mon-Thurs, book 2 nights, get a 3rd free! 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.

29 Dec – 5 Jan

$401 SGD per night

Guest favourite

Flat in Rockford

4.94 out of 5 average rating, 452 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.

26 Aug – 2 Sep

$139 SGD per night

Guest favourite

Bungalow in Rockford

4.95 out of 5 average rating, 379 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.

28 Jul – 4 Aug

$147 SGD per night

Guest favourite

Home in Rockford

4.97 out of 5 average rating, 150 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, & 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.

29 Sep – 6 Oct

$142 SGD per night

Guest favourite

Home in Cherry Valley

4.92 out of 5 average rating, 119 reviews

Charm in the heart of the Valley

Charming 4 bedroom 2 bath home in the heart of Cherry Valley. Walking distance to local restaurants, bars, gaming facilities, and peaceful park. Large shopping mall and water park within minutes. Home has Ring security cameras at each entrance. Two smart televisions with Netflix. Available wifi at 1 gigabyte per second. Touch pad lock for easy check in/out. Sleeps 8 with 2 queen beds, 2 twin beds, and 1 queen pullout bed.

24 Jun – 1 Jul

$193 SGD per night

Guest favourite

Home in Rockford

4.86 out of 5 average rating, 153 reviews

Cozy Ranch with family game room

Welcome!! Come and enjoy staying in this recently renovated Cozy Ranch!! Situated in a perfect location, very centralized, close to everything! Grocery stores, restaurant, Hospitals, golf course, university, museums all are within 10 minutes away. Magic water, great America and other attractions are around 8 minutes away.

10–17 Jul

$203 SGD per night

Guest favourite

Loft in Rockford

4.93 out of 5 average rating, 404 reviews

Jackson’s Urban Retreat + Patio

Cool, modern downtown city loft located walking distance from 20+ restaurants, shops and entertainment venues. Private outdoor patio and private parking spots. If you are looking to enjoy sports, dining, arts and theater without getting in a car, this is the space for you. Located above Abreo Restaurant, all guests receive 10% discount during stay

31 Aug – 7 Sep

$164 SGD per night

Guest favourite

Home in Rockford

4.98 out of 5 average rating, 170 reviews

Holste Cantina, a place to enjoy quiet nature.

Bunted next to Aldeen golf course. A short walk to club house if you like to play. No street traffic. Only a mile or two from any shopping needs. Deer and turkeys are common. No parties aloud. It’s a wonderful place to relax and enjoy with family.

18–25 Oct

$567 SGD per night