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.

Wonderful home with lots of charm. Hosts really thought of everything to make your stay comfortable and enjoyable.

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!

Home was fantastic for a family trip! Lots of room for everyone and incredibly clean and cozy! Eileen was a wonderful and accommodating host! We hope to be back!

Kim was very friendly and so easy to work with. She was quick to respond to any questions that we had. The lake house cottage was very clean and exactly as pictured. We will definitely rent with Kim again!

We loved staying in this adorable lake house in New Buffalo! It's a perfect location and is within walking distance of many restaurants, coffee shops, and the beach! This house was ideal for a large group and housed 10 adults and 3 children comfortably. I would definitely recommend staying here if you're planning on coming to New Buffalo!

Super clean, great space. We will keep this one on the short list for another visit!

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.

This listing was all that the hosts described it to be. Lots of natural light, comfortable Chicago living, and close to transport for quick access to downtown. The hosts were responsive and answered a few messages I had promptly throughout my stay. I’d recommend this place to anyone looking to visit the Chicago area and wanting to distance themselves from the middle of downtown, as well as those looking to be close to downtown but wanting to avoid the prices that come with rentals closer to the city (my situation).

Very nice Victorian home. Great location

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!

Our stay at Jaime's place was perfect. We worked a convention at Donald E. Stephen's convention center and it was about 15 minutes from there, which was perfect. we felt right at home and Jaime showed us around the place, eventhough we got there late. The bed in the master bedroom is so comfortable, I didn't want to get up from it 🤣🤣 I loved the window in the shower. She gave us a lovely recommendation for breakfast that we loved. I would definitely stay here again.

This home in Chicago was exactly as advertised. Perfect for a girl's weekend in Chicago. Plenty of space for sleeping, large bathrooms with plenty of mirrors to get ready. The house was well stocked with everything we needed for a perfect weekend. The location was great too. was able to walk to bars and restaurants or take short Uber anywhere we needed to go. Having off street parking made it even better for out of towners who drove to the destination. I would definitely book again when traveling with a large group.

Had a great stay at Steve's place with my friend and our 2 dogs. Nice quiet neighborhood.

This place was stocked with anything you may have forgotten. She left us some home made muffins. The place was clean and perfect for us. It was between downtown Plymouth and Culver so lot’s to do and restaurants. Brought our dogs. It worked out well. I will definitely stay again

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.

Booked the A unit with friends for a wedding hosted at Lakeside Inn .02 miles away.. The kitchen was great, furniture comfy. Steep stairs so may be hard for older folks, but there are two bedrooms on 1st floor. We did not use the hot tub or pool, so no comments. Loved the front room and screened in porch. Lots of options to sit, visit, play games. Nice to be able to seat 10 at the dining room table. We had the property to ourselves, there is a B side, so no issues with neighbors. Shared some feedback with Frank and he appreciated it. If you have a big group—you would love being side-by-side. The unit was great with two nice bathrooms to get ready for wedding! Thanks Frank!

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.

Geoff is an amazing host and the house was beautiful. Our group was so happy with our stay. I highly recommend this property.

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!

Joel and Kathi's place is beautiful and very spacious. Kitchen is well-stocked. Lots of sleeping options. Be cautious if you have mobility differences as the only way to the second floor is the spiral staircase. However, all amenities (bedroom, bathroom, kitchen) are available on the first floor. Would love to come back!

Beautiful condo in a fantastic location. Great sunsets from the balcony. Would absolutely stay here again.