Guest house holiday rentals in Illinois

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.

Pool, Hot Tub and Dog Paradise

As of 10/13/25 the pool is closed. Located close to Scott Air Force Base and STL. Home is on 5 acres and has plenty of privacy. Beds are memory foam mattresses. Heated pool (Mid-May - Mid-September). Pet friendly (dog/cat) & have 1 Large kennel and 1 small pet carrier we can set up. Our home has a large circle drive that goes behind the barn. There is room for Handicap parking, the gate and sidewalk to the main patio are 48 inches wide. We have a handicap shower seat. We live on the property.

Riverfront Beauty

Take it easy at this unique and tranquil getaway. on the Illinois river, large waterfront yard with Geese, Great Blue Herons, Egrets, White Pelicans and Eagles showing up on a regular basis. Close walking distance to grocery store, liquor store and downtown restaurants and bars in peaceful Ottawa, Illinois near Starved Rock State Park. Upper level (has stairs) 2 bedroom overlooking the Illinois River, play in the large yard or build a campfire in the fire pit next to the river and just chill.

Cozy cabin on farm near Jerseyville and Grafton IL

No cleaning fees! Relax in this cozy cabin on a 30 acre farm w/beautiful views & peaceful surroundings. Near shopping, wineries, nightlife, hunting & fishing. Abundant wildlife & farm animals-horses, cows, chickens, goats, sheep, geese. Two bedrooms (one in a spacious loft) with a queen sofa sleeper in the living room. Full kitchen w/dish washer. Fireplace & cathedral ceilings in living room. Full bath w/shower. Covered front porch. Screen porch off living area w/outdoor seating. Fire pit.

HighviewCountry Escape-log home-family farm w/view

Whether you want a staycation or just a weekend away, we have the place for you! Quiet secluded setting, with spectacular view, on one of the highest hilltops in Illinois! Morning sunrises are exceptional. Evening sunsets are breathtaking. Starry nights are amazing. Something in every season! Not far from Galena and other small towns that offer charm, restaurants and shopping. Our rental is fully independent and has everything that you need for your getaway. Please see all photos.

Private Guest Lake House On 37 Acres In Country

Private guest lake house, located next to main house, on private lake in the country. 2 bedroom, 1 full bath, full kitchen, washer and dryer and large attached screen porch. Private 37 acres of woods and prairie. Fishing and walking trails. Great window views of lake, woods, prairies and river valley. Please note, this guest house is located 1 mile down a county maintained gravel road. 25 minutes from Galesburg, IL, 20 minutes from Monmouth, IL and 35 minutes from Macomb, IL.

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by a German mason. This upper unit Apartment is a spacious 1,100 square feet, lovingly restored with a vintage aesthetic in 2018. The private entrance to "The Apartment" will lead you to; 2 cozy bedrooms & 1 vintage inspired yet modern bath with walk in shower. A large living room, dining area and bright clean kitchen will make you feel right at home. 9 foot ceilings and tons of natural light through out.

Carbondale Pool House - Sauna, Hot Tub, Dogs OK

Rated in “Top 1%” by Airbnb, 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 and friends of the Pool House on the grounds, gardens or pool. Hosts are Jane, anthropologist and D. a retired photojournalist for the New York Times.

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

ThE HiDeAwAy

You’ll be surprised by what’s inside! We’ve designed this space to be more than just a place to stay — it’s an experience, because isn’t that what life’s all about? Perfectly located just two blocks from the town square and only steps from the iconic Million Dollar Courthouse, you’ll also be close to great restaurants and shops. Whether you’re visiting for family, business, or a well-deserved getaway, we hope your stay with us creates lasting memories.

River Beach Guest House

Welcome to River Beach Guest House! Where modern meets relaxation! Completely renovated and private 1 bedroom getaway with beach access where you can enjoy beautiful river sunrises and sunsets and eagle watching! Just a 6 minute drive to downtown Chillicothe, 60 minutes to Starved Rock State Park, 18 minutes to beautiful Grandview Drive in Peoria Heights, or just 23 minutes to downtown Peoria.

The Main St Carriage House - a charming cottage

This is a charming 1 bedroom 1.5 bath cottage located in the heart of Carmi. Enjoy the fully stocked kitchen, dining table for 4, high speed Wi-Fi, two smart TVs, 1 queen bed upstairs with a half bath, with a full Bath on the main floor, and a private parking spot. We also have a 25amp Level 2 charger available upon request for anyone needing to charge their EV while they stay!