Family-friendly holiday rentals in Gary

Voted #1 Family Getaway In SW MI for 2019-2024

Welcome to our home away from home. Spacious, comfortable interior and large wooded lot. 8 blocks to the beach - 4 blocks to downtown shopping, restaurants, bars etc. We have thought of everything to make your stay enjoyable and carefree. Sleeps 10 -12 comfortably. Our large decks, brick patio and backyard, make our home a great place to come back to after spending the day at the beach, touring wineries & craft breweries, or taking in the beauty & fun activities southwest Michigan has to offer

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 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

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.

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. 

5 BR Cottage with Pier Street Beach Access

Wonderful classic cottage that has been updated with all the amenities that you would expect in a premium property. Centrally located to all that Harbor Country has to offer. Antiquing, wineries, art galleries, unique shopping and biking and hiking trails are minutes away.