Holiday houses in Riverdale

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Romantic Escape ~ Adult Playhouse w Exotic Dungeon

🎉 New Year Romance Special — 10% Off New Year. New desire. Start 2026 by heating things up. 🔥 Today only. Limited availability. 🌹More than a stay — a private, immersive romantic experience crafted exclusively for adult couples who want something unforgettable, intimate, and truly one-of-a-kind. Every detail is intentionally designed for passion, connection, and high-end luxury you won’t find anywhere else. 💌 Want to elevate your night? Ask about our curated romance packages.

W2 15 min to Downtown Next to UniversityTrainPark

☞ 1 Smart TV ☞ Fully equipped + stocked kitchen ☞ Self check-in ✭“Great stay would definitely come back again ” ☞ Luggage storage available ☞ Onsite washer + dryer in basement ☞ Air conditioning 》35 mins to airport 》15 mins to Downtown Chicago 》Minutes drive to McCormick Place convention center, museum campus 》 Minutes walk to train station 》 Walking distance to University of Chicago 》 Across street from parks Minutes walk to train station 》2 bedroom, 1 bathroom 》Sleep 6

Homewood Oasis

Welcome to our Homewood Oasis, where relaxation meets family fun! As former residents of this charming town, we know the importance of a comfortable and enjoyable stay when coming back to visit. Our Airbnb is more than just a place to sleep; it's a carefully curated space designed for families like yours. As hosts who've experienced the need for a home away from home, we've put our heart into making this space welcoming and enjoyable for you. We look forward to hosting you!

Boulderstrewn: Historic Homewood home

Charming and historic Sears Catalog House on 2/3 acre wooded lot. Less than 10 minute walk to shops and restaurants in downtown Homewood to Metra rail (and Amtrak) station with express service to Hyde Park and University of Chicago (less than a half hour) and Chicago's 3 magnificent downtown waterfront stations (~40 minutes). Fire pit in yard can be used to enjoy summer nights. No cable, but several digital antenna channels available as well as Netflix, XBox and DVDs.

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Guest Suite w/Private Entrance Beverly Basement

Great location. recently upgraded. Space: This is a new guest suite in the basement of my home. The suite is equipped with a full kitchen featuring high-quality appliances. The suite includes a large bathroom, a bedroom with a new queen-size mattress, and a washer and dryer onsite. The suite offers a peaceful and comfortable place to stay. A 2 block walk will get you to the commuter train, Subway sandwiches, an Italian deli, CVS Pharmacy, and Starbucks.

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Modern 2BR/2BA Condo | Spa Bath + Free Parking

Enjoy the entire condo to yourself in this clean, modern 2-bedroom, 2-bath home, designed for comfort and convenience. Perfect for couples, families, or business travelers seeking a quiet, cozy stay. Enjoy a full kitchen, spa-style bath, and free street parking. Minutes from UChicago, McCormick Place, Soldier Field, Shedd Aquarium, and quick access to I-90, Lake Shore Drive, and downtown Chicago.

Cozy Guest Suite. Private Entry+ Turo Rental

3600 sqf single family home with a Guest Apartment and private entry on the ground level. Your family will be close to everything when you stay at this centrally-located place. Centrally located off of I294, I55, I57 and I80. Easy to and from travel. In Need of a rental we have 2018 Jeep Grand Cherokee High Altitude at the house and listed Turo.

Ultra Modern Beverly Suite

This stylish place to stay is perfect for any event. 420 friendly. Come and let us pamper you. Come and enjoy are tree lined community in the historical Beverly area. This Suite has all the latest amentities and beautifully furnished. The whole group will be comfortable in this spacious and unique space.