Family-friendly vacation rentals in Chesterton

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.

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!

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!

Our group of 8 friends enjoyed our stay very much. The house was nicely furnished and the kitchen well-equipped. Given that the weather wasn’t great for beach days, the hot tub was a very welcome feature. Our only quibble was that closets were lacking or locked, leaving guests without a place to hang clothes. Prospective guests might also want to know that the three upstairs bedrooms share one full bath, with the second bath en-suite in the first floor bedroom. All in all, the house served us well for a long weekend getaway.

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

Great place to stay. About an 8 minute drive to Notre Dame University.

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.

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!

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 .

Cute, quaint and private cottage with a nice, large and completely fenced in backyard which is great if you bring the family dog. Good communication from host. No issues.

First time staying at this rental . Was super cute & charming. Very well taken care of. Will definitely book again.

Rhonda was a wonderful host. The place was beautiful and the lake peaceful. We loved the firepit!

What a beautiful location! Loved all the trees, beautiful yard to play games, super big fire pit, deck and grill was spotless! The inside was nice and spacious for the size. Great kitchen and bathrooms. The basement was large! We had an incredible time. Would come back for a longer vacation!

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.

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.

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 !

Barry's place was perfect for a fun trip with some work friends. It was extremely warm the 2 days we stayed so the pool was a welcome amenity. We had a lot of fun at Barry's between the pool and hot tub and the various activities to do on the property alone. There was more than enough room for all of us as well. It was a peaceful location while also being nearby to stores, resturants and fast food places. Barry was responsive to any questions we had and everything in the home was just as listed. The rules and check out instructions were clear and I would definitely recommend Barry's place to anyone looking for a fun and relaxing time, especially in the warmer months in order to ultize the huge pool.

The house is great! Being so close to the park was perfect for our kids. The golf cart is a must when you are in this part of the resort. There were beach chairs and a few beach toys there. The house was spacious. We have stayed many times in the Beachwalk resort and have loved it every time. So much to do and our kids have a blast.