Family-friendly holiday rentals in Crown Point

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

Perfect spot: 3 FULL baths, 4 bedrooms

All photos are 2025. 4 large bedrooms, 3 FULL bathrooms all separate from bedrooms. Easy walk to academy, Lake Max, ALL restaurants & stores within 2 blocks. Big yard/large deck w/ grill. Washer/dryer, DISH, WiFi. 1 bedroom, 1 full bath downstairs, no stairs for either for older or special needs. 1-night weekday rental ONLY allowed in winter. Central Air + additional room units if someone wants even cooler for sleeping. Annual leader in return rentals in Culver for a reason. Affordable.

Cozy, Private & Inviting Tulip Tree Beach Cottage

Beautiful renovated beach cottage on a quiet tree-lined street. Private comfortable home perfect for a winter weekend away! Enjoy the best of Pure Michigan, 2 mi from Sawyer & 0.5 mi to Warren Dunes State Park. Plenty of outdoor space to play, skylights to soak up the natural light and central to wineries, restaurants and the Dunes. Grab local farm fresh produce, s’mores for the firepit and a local natural wine to sip as you watch the sun set from the huge back deck and large backyard.

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.

Charming Cabin-Private Beach & Golf

Why the rave reviews? This cabin is a unique and charming 2 bedroom retreat that sits atop a hill and is surrounded by elegantly sculpted terrain of Harbor Shores golf course and walking trails. The private beach on Lake Michigan is steps away. It is located in a quiet neighborhood and is close to family fun activities in St. Joe/Benton Harbor, fantastic restaurants, wine tasting, art galleries and quaint shops.

SoulShine Inn • Pets Welcome•Fully fenced backyard

Near Warren Dunes, the Galien River, breweries, and wineries. Relax here with a fully fenced yard, fire pit and patio for grilling and privacy. Darling, pet and child friendly Tiny House . Two bedrooms on one level with a queen bed in each. An extra loft for an additional sleeping space for two. The ladder to the loft is steep(pictured)This tiny house sleeps 6. Nema 14-50 outlet for EV. Bring your cord/plug

Private, Sun-filled Union Pier Cottage

Sunny, private cottage set on a half-acre facing woodlands. Quick drive to everything - beaches, hiking, restaurants, wineries, breweries, etc. High-speed internet available and desk with two monitors. Please be advised: reservation requests from first-time AIRBNB renters will be declined. You must have rented through AIRBNB in the past and received a high rating.

The Bright Yellow Retreat

The Bright Yellow Retreat is a pleasant, short walk to Lake Michigan beach. Our sunny, vibrant home sleeps up to six guests. Our open floor plan with plenty of windows offer bright and airy surroundings. Relax in our sunroom. The large back yard is well equipped with grill, lawn furniture and picnic furniture. And, pets are welcome.

Airy and bright, Cottage Blue Welcomes You!

Nestled in the walkable Sheridan Beach area of Northern Indiana’s gorgeous and expansive lakeshore along Lake Michigan. Comfortably sleeps 12 - 14 with the perfect amount of space to get together and getaway to your own private spaces. Please note that parties are not allowed and you must be 25 years or older to rent our home.