Family-friendly holiday rentals in Homewood

Tryon Farm "Bees Place" 100 acres of nature/trails

Charming 2 bed 2 bath, unique modern barn house. Relaxing screened three-season porch. In warm weather hammock is up and ready for you! Private courtyard with Gas Grill/Swing. Chilly weather come warm up next to the wood stove. Large overhead windows offer natural light & night sky views. Great views throughout. Leashed pet welcome. Tryon Farm community offers over 100 acres of wooded walking trails, a fishing pond & tree swing. One mile to Shady Creek Winery, close to beaches, and brewery’s.

Charming Yellow Cottage Near the Beach

Relax and unwind in our cozy house, just a quick 0.2-mile stroll from the shores of Lake Michigan. Whether you’re planning a family getaway, a friends’ retreat, or a peaceful solo escape, this 2-bedroom home blends comfort and convenience, accommodating up to 6 guests. Tucked away in a serene neighborhood, it’s the perfect spot to recharge. With its inviting vibe and prime location near the beach, dining, and local attractions, this retreat is your ideal home base for a memorable coastal escape.

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 18 min walk for trains to city, 5 min drive to lake. Wifi

Best Deal In Michigan City 1.3 miles to Beach

Quiet for a well deserved nights rest. Plenty of space for 4-8 guests indoors and out. Short drive to the Washington Park beach & zoo Walking distance to south shore train for a quick ride into the heart of Chicago. Less than a mile from uptown arts center and district Short drive to The National Lakeshore, that has great beaches, hiking, and biking trails! Have a day in the sun, and come back to relax, in a quiet backyard patio area equipped with grill & night lighting... Must be 24 to book

Dunefarmhouse Modern Country Escape

Experience nature and design in an unforgettable way! This thoughtfully curated home is located within a unique green community surrounded by 200+ acres of woods, prairies and meadows - yet minutes to the beach, great restaurants, wineries and activities in harbor country. A unique and immerse art experience awaits every guest. Dunefarmhouse was featured in TimeOut magazine in 2019-2020, as a "Top 10 Airbnb rental in the Midwest" and part of "Perfect Midwest Getaways."

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

Quaint Batavia Coach House

The Coach House is located behind our house. It is a private and separate little house. It is located close to the river path and lots of restaurants. The upstairs is one big room that has 1 queen and 2 twin beds. The upstairs also has a full bath. The TV in main living area on first floor is not hooked up to cable, but you can log into all of your apps and have access to news via YouTube TV, Netflix, Prime etc.

Beautiful home with Beach views in Beachwalk

Enjoy the open concept family room/dining area, flat screen TV, fireplace, and a farmhouse table that seats 12. You can also enjoy the sunset from the top floor "birds nest" with views of the Chicago skyline. The lower level is perfect for kids to watch TV and play games and is equipped with bunks that sleep up to 7 people. A Staircase leads to a private walkway for access to Lake Michigan.

Clean, spacious, walk to Wrigley! Self check-in!

Park your car and forget it- or just leave it at home! Charming 3 BR first floor apartment in a Victorian building in the ultimate location, perfectly situated between Wrigleyville and Lincoln Park in the beautiful, vibrant Lakeview neighborhood. Guys seriously… this is the ideal neighborhood for a Chicago getaway or visit with family.