Holiday rentals in Homewood

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

Suburban Haven: Cozy Escape with a Touch of Luxury

This newly updated home is the perfect place to enjoy some peace and quiet. You’ll find ample seating for your whole group, and sleeping accommodations for up to 16. Using this as a homebase, you can enjoy everything Chicagoland has to offer. This home is perfect for reunions, family getaways and vacations. You’ll find a light and airy home that is beautifully decorated and tastefully furnished, with everything you need in ready supply. Enjoy a restful stay in this beautiful suburban getaway!

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more

GLAMPING FUN April - Nov Winter Glamping sleeps 8 RV, Gazebo & Safari Yurt closed. Includes heated event yurt, Game room, and Hot Tub in Winter. No additional fee for event yurt in winter for 8 guest. RV w/bathroom - 2 beds 20' Safari Yurt - 4 beds Game Room w/bathroom queen & sofa sleeper Gazebo 2 twin beds Wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs (seasonal) mini golf 3-n-1 Court; Event Yurt add on $180 up to 15 additional non/overnight guest

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.

Romantic Escape ~ Adult Playhouse w Exotic Dungeon

🎉 New Year Romance Special — 10% Off New Year. New desire. Start 2026 by heating things up. 🔥 This weekend 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.

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.

Charming Homewood Away from Home

Keep it simple at this cozy, charming brick ranch tucked away on a quiet, friendly street. Just minutes from the Metra line for an easy ride into downtown Chicago, and close to all the great local shopping and dining in downtown Homewood. House Guidelines: • No smoking, no parties, no large gatherings • Be mindful of neighbors • Narrow driveway, limit 2 cars • No extra guests without notice • Pets are welcome, but must be added to your reservation • We have a moderate cancellation policy

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.

Peaceful- Home in Tinley Park

Our exquisitely furnished three-bedroom, one-bathroom home in Tinley Park, IL, is ideal for up to six people and features contemporary décor, a fully functional kitchen, and roomy living rooms. Unwind in the expansive garden or visit the area's best dining options, retail establishments, and tourist sites. Take advantage of the ease of being close to airports and downtown Chicago, with Wi-Fi and on-site laundry available for your

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.

Updated, bright, and modern, 3 bedroom home.

You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi