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Guesthouse vacation rentals in Illinois

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Top-rated guesthouse rentals in Illinois

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

Guest favorite
Guesthouse in Carbondale
Homestead Cottage
Enjoy tiny farmhouse life in this adorable 375 sq. foot cottage. Loaded with everything you need this little cottage is nestled privately behind some trees on our 11 acre farm. You will soon forget how close you are to town with the beautiful view from your windows and the pasture fence just steps out the back door. Whether you’re here for the wineries, amazing hiking, an SIU event (3 miles) or to visit with family, the Homestead Cottage will provide a comfortable retreat from any adventure.
$89 per night
Guest favorite
Guesthouse in Carbondale
Carbondale Pool House - Sauna, Hot Tub, Dogs OK
The Pool House is a separate cottage surrounded by gardens and swimming pool, with retro "Danish Modern" furniture, a gourmet kitchen and plush beds. We have recently added a Finnish Sauna and Japanese Ofuro Soaking Tub. We accept well behaved dogs for a fee of $35 a night. We allow only guests of the Pool House on the grounds, gardens or pool. Covid protocols are followed. Hosts are Jane, anthropologist and D. a retired photojournalist for the New York Times. City License # 24-04
$229 per night
Guest favorite
Guesthouse in Chicago
Private Coach house near Lincoln Square!
Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, Ravenswood, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or just crack open a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 2 miles north of Wrigley. Pets Allowed!
$84 per night

Popular amenities for Illinois guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Chicago
Cozy Coach House
$60 per night
Guest favorite
Guesthouse in Urbana
Private Studio Loft for People, Pets, and Yoga
$63 per night
Guest favorite
Guesthouse in Harrisburg
Spring is coming soon: Shawnee Forest Time!
$135 per night
Guest favorite
Guesthouse in Berwick
Private Guest Lake House On 37 Acres In Country
$155 per night
Guest favorite
Guesthouse in Wheaton
Cozy private coach house in Wheaton
$111 per night
Guest favorite
Guesthouse in Batavia
Quaint Batavia Coach House
$75 per night
Superhost
Guesthouse in Chicago
Coach house Wicker Park- Bucktown
$135 per night
Guest favorite
Guesthouse in Chicago
The Rectory
$192 per night
Guest favorite
Guesthouse in Oak Park
Coachhouse in central OP 4 blk to L
$150 per night
Guest favorite
Guesthouse in Evanston
Coach House Art Studio, By Downtown & Northwestern
$150 per night
Guest favorite
Guesthouse in Golconda
Shawnee Pines Lodging Cute Studio - Cabin #2
$109 per night
Guesthouse in Kampsville
The Watkin's Place at McCully
$100 per night

Guest house rentals with a patio

Guest favorite
Guesthouse in Eureka
Artist Loft
$75 per night
Guest favorite
Guesthouse in Wilmington
Catfish cabin
$95 per night
Guest favorite
Guesthouse in Jerseyville
Cozy cabin on farm near Jerseyville and Grafton IL
$140 per night
Superhost
Guesthouse in Chicago
Private Coach House / Easy Commute
$109 per night
Guest favorite
Guesthouse in Ottawa
Riverfront Beauty
$110 per night
Guest favorite
Guesthouse in Urbana
Private Guest House Near Campus
$90 per night
Guest favorite
Guesthouse in Carmi
The Main St Carriage House - a charming cottage
$115 per night
Guest favorite
Guesthouse in Quincy
Morgan Creek Carriage House
$109 per night
Guest favorite
Guesthouse in Geneva
Eclectic Downtown Geneva Gem
$100 per night
Guest favorite
Guesthouse in Elgin
Carriage House
$150 per night
Guest favorite
Guesthouse in Villa Park
Tranquil Pondview +New Kitchen
$120 per night
Guest favorite
Guesthouse in Grafton
Pineapple Cottage
$199 per night

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Evanston
Cottage in a Garden
$98 per night
Guest favorite
Guesthouse in Chicago
Polk Street Coach House Apartment, Little Italy/Medical Dist
$114 per night
Guest favorite
Guesthouse in South Elgin
Private studio apartment on the Fox River
$82 per night
Guest favorite
Guesthouse in Countryside
Cozy Cottage Minutes from Downtown Chicago
$95 per night
Guest favorite
Guesthouse in Mascoutah
The Carriage House
$74 per night
Superhost
Guesthouse in Chicago
Private Studio in Bridgeport, Chicago
$55 per night
Guest favorite
Guesthouse in Lake Forest
Large Luxury Guest Apartment in the North Shore
$200 per night
Guest favorite
Guesthouse in Monee
Tranquil Coachhouse Studio Apartment
$110 per night
Guest favorite
Guesthouse in Oak Park
Stylish Coachhouse in lovely Oak Park!
$113 per night
Guest favorite
Guesthouse in Marion
Hip-Young-Fun LAKE HOUSE Guest Suite
$112 per night
Guest favorite
Guesthouse in Belleville
Everwood Cottage ☀ TDY Mil / 🐶 welcome!
$123 per night
Guest favorite
Guesthouse in Chicago
Quiet, Cozy 1-Bedroom Carriage House in Chicago
$92 per night

Destinations to explore