Family-friendly vacation rentals in Gary

Was an absolutely relaxing stay. It was exactly what my husband and I were looking for. An extended weekend away with a bunch of things around us to do. It had a little bit of everything around us, including privacy. It was fantastic.

Had a wonderful stay at the Townehouse in New Buffalo. Beautiful home. Loved all the outdoor patios and enclosed seating area. Spacious rooms and fully stocked bedding and linens. Perfect location right downtown. Walking distance to beach and shops and restaurants. Couldn’t ask for a better spot. Mark was very friendly and accommodating. Can’t wait to go back.

Our host was extremely tentative and helpful. We really enjoyed our stay at the home. It was big enough to accommodate our family plus a few other visitors, plenty of beds, plenty of living space so people didn’t have to be on top of each other. Very close to downtown and the blue line which made going to the airport and downtown much more accessible. we didn’t even have to rent a car.

Our stay in Three Oaks at Ivan & Carly's place was great! they knew we were checking in at night, and when we got to the house, there were lights on, which I thought was a very nice (and helpful!) touch. The instructions to get in the house were clear, and the house was lovely. They knew we were bringing out kids, and had snacks out for them and even a bottle of wine for us! I wish we had been able to stay longer, because the house was very cozy and the location was great! We went to Oaks Eatery for breakfast, and it was the best breakfast we have had in a long time. We would definitely stay at this house again! Ivan & Carly were very communicative, and had we needed anything, I know they would have been responsive. Great stay!

Jen was so sweet, messaged back right away and gave us a list of things to do while we were there on a mini vacation visiting family. Hot tub and deck so clean, amazing and private Thank you and Happy holidays.

My fiancé and I visited Donna’s place over a summer weekend, and we had the most amazing time. Donna’s house is so beautiful and welcoming - we felt at home. Her place was clean and is filled with the most thoughtful decor. It has everything anyone needs for a peaceful, relaxing stay. She was responsive right from the day of booking to our final day and even stopped by to meet us in person. We look forward to staying at her house again soon!

Birthday brownies upon arrival! Great quiet location but very convenient for local shops and restaurants. Can walk to the beach! Can’t wait for the opportunity to visit again

My daughters and I celebrated Easter at Kim’s cottage It’s clean, beautifully furnished and she is extremely responsive (I mentioned I forgot OJ on the phone and she was in the area and she left two OJs at the door) The cottage is cozy and fun We grilled, dyed eggs, watched movies, played a board game and loved the hot tub It’s clean clean !!! Just book it It’s a jewel box

We enjoyed our short stay- the home was comfy and had everything we needed. We especially enjoyed the short walk into town where - plenty of restaurants and gift shops. We will definitely return.

Kyle's apartment was a visual feast, with fun and eclectic decor, furniture, and artwork! The listing states some quirks, which was accurate, but nothing that diminished the quality of our stay (for our family of 3). We didn't have a long enough stay to enjoy the full kitchen and dining table much, but would be a well-supplied kitchen for preparing full meals. The shower had some quirks but luckily Kyle even prepared a Youtube video to show and describe exactly how to turn on the shower. Part of the quirks of an older apartment building is radiator heating, which gives some 'clanking' and other annoying noises at times, so if you're noise-sensitive that's something to keep in mind. Kyle's local guidebook was helpful (unfortunately too long of waits at the places we had hoped to try) but found other options in the area for dinner. Our family of 3 had plenty of space for sleeping and lounging. This is a really cute space in a great location and a good close to downtown spot.

We had a fantastic stay! The space was clean, spacious, and well-equipped with thoughtful extras that made traveling even easier. The host was incredibly friendly and communicative, ensuring we had everything we needed. One of the highlights was the fenced-in yard, which was perfect for our dog. We truly appreciated all the little details that made this stay comfortable and enjoyable. Highly recommend!

Alexandra’s place was a great place to stay for our group. We had two families, including 7 children, and it was great to find a place with so many queen beds to accommodate all our different sleeping needs, that also had easy access to public transit and neighborhood attractions and still had a great space where we could gather and have all of us play games/eat together comfortably after a day in the city. This was a very good experience.

Jamie’s place was a perfect spot to stay in Chicago. There is access to the L within a few miles (with parking structure), and there are many walkable places locally. We highly recommend Caesar Pierogis on West Irving (offers gluten free pierogis). The neighborhood is charming and safe for walking. After long days of exploring, we came back to Jamie’s place and enjoyed watching Netflix and relaxing in the living room. The kitchen is stocked with utensils, and there is a grocery store within walking distance. Jamie is a very thoughtful host, and her home is quite accommodating. We had a lovely get away. Thank you, Jamie!

We 3 loved our stay at Joseph and William's place! The apartment was clean, bright, and filled with art. The kitchen was lovely, the beds were all comfortable and the shower was very hot. We loved the back deck, and I imagine it gets used so much in warmer weather. The location is perfect. We walked to restaurants and shops in Andersonville. It was just minutes from Loyola Univ. which is why we were in town.

My friends and I greatly enjoyed our stay over the weekend while visiting for a friend’s wedding. Steve’s home was comfortable, clean, and accommodating to our needs. We would definitely stay again!

Enjoyed our stay at Sue’s place. Beautiful inside and it felt like home. She has it stocked with everything you need and she left snacks and muffins that were delicious. Definitely will be back .

Beautiful little cottage. Great location, walkable to the beach and an easy 10min drive to restaurants and shops. Perfect for families any time of the year. The only things to keep in mind is it a shared pool/hot tub and Cottage A is right next to the pool.

Awesome stay! Booked here for a nice relaxing weekend get away where we wouldn’t need to travel to have fun. That is exactly what this place offered. Great pool & hot tub, and house has plenty of room making it feel relaxing and gives everyone plenty of space. Easy walk down to the beach - you get to leverage the private side of the beach which is very very nice. Overall great stay and will look to book again!

Such a cute home. Right across the road from the Warren dunes. Easy to get back and forth with a bicycle. The cutest little ice cream shop right next door. Bed was comfortable and the bunk beds are roomy. Would definitely stay here again.

Fantastic location, felt incredibly safe, and was exactly as described. Great space and made for the perfect spot for our family during our stay in Chicago. Would absolutely return.

House was beautiful and well kept. It had everything we needed for a girls weekend. We also loved that the house had lots of personal little touches that made it feel very welcoming!

Beautiful home! Easy walk to the beach or stay back and enjoy the pool and hot tub! Spacious backyard and plenty to do for everyone! Everything was clean, very clear directions on how everything worked and even provided some recommendations for things to do nearby. Thanks for the hospitality!

Katherine was absolutely amazing! Very quick to redoing to questions. She gave great instructions, along with a lists of recommendations. Her unit was spotless and cozy. So comfortable that we decided to stay in instead of go out.

Tom and Charyl were amazing hosts ! We had open communication throughout our stay and even got a tour upon our arrival. The airbnb was everything as described and more ! The pool was incredible and the airbnb was only a 5 minute drive to the nearest beach. They even had a binder of recommendations available to us of local attractions/things to do. Our expectations were exceeded for this trip, and we can’t wait to come back !