Family-friendly holiday rentals in Hazel Crest

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.

“Treetops” Charming Country Coach House

Second-floor comfortably furnished coach house. Stylish and airy space with full kitchen. Great views. Private in-ground 20' x 40' swimming pool reserved exclusively for you and your guests. Basketball half-court. Softball diamond. Bocce court. Great for bicyclists. 20 acres of woods. Hiking trails on property and pond with wildlife. Centrally located between New Buffalo, MI, and Michigan City, IN. Close to the Indiana Dunes, and Lake Michigan. 70 minutes to Chicago, 45 minutes to South Bend.

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."

Eagle's Beach Nest: Pet-Friendly*Fenced*Walk2Beach

Nestled in New Buffalo's heart, this cozy retreat is a stone's throw from key attractions. The beach, Marina, and esteemed Bentwood Tavern lie within a mile. Venture a tad further to Stray Dog or the town center. Four Winds Casino is a quick 10-min drive, with Blue Chip Casino just 15 mins away. Ideally positioned amidst Harbor Country, nearby renowned wineries beckon. Perfect for girls' getaways, family trips, or group gatherings, and pet-friendly to boot!

Charming apartment in Arts District

Walk to outlet mall, art galleries, parks, restaurants, and Lake Michigan beach. Walk or drive to casino. This is a 2nd-story apartment in Michigan City's historic homes. A full 1,400 sq ft of space! Fully appointed, clean and beautifully decorated. Newly renovated kitchen and bath. WIFI. Access to beautiful back yard patio and deck. Great proximity to attractions. Great for couples, solo adventurers, and families with children.

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.