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.

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!

Great place to stay and the local area was absolutely gorgeous! We definitely appreciated how the host provided a binder full of local restaurants, instruction manuals, and places to visit! Not to mention, heated bathroom flooring was life changing! Thank you again ♥️

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!

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 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!

We all agreed that Deb’s Place was one of the best places we’ve stayed. The location was perfect…very walkable to all the shops and restaurants of New Buffalo, but also so easy to hop in the car and drive to Art Attack in Three Oaks or Greenbush in Sawyer. We loved that we had our own bedrooms plus two baths to share among 5 of us. The yard was awesome and the only bummer was it was too cold for us to enjoy the fire pit or the hot tub (32 degrees on April 26th? Crazy!). Deb was easy to communicate with and the place was perfectly decorated and had all of the little amenities that made it feel like home. Overall, a great place to stay any time of year!!

Cary communicated very well as to when the house would be ready. Check in was easy and the house was clean and comfy, perfect place for pets!

Very clean and well-maintained. Plenty of towels, pillows, supplies, etc. were provided. It was so nice to have a washer, dryer, and dishwasher. There was a book on the desk which the Host put together sharing nearby attractions, breakfast & dining options, wineries, etc., which was so helpful. We enjoyed the screened-in back porch, deck and great backyard. The kitchen and bathroom cabinets provided all the amenities we needed without having to run to the store for things. We loved the close proximity to the beach, restaurants, grocery store and unique local shopping. Great communication from the Host who was very helpful and welcoming. We would love to come back again and next time make use of the backyard grill and firepit!

Great place - beautiful space, conveniently located to pretty much everything. We had a great quiet long weekend in March before everything gets busy. Great hosts!

We love Sue’s place! Our home away from home! We have been many times and always enjoy our stay!

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.

Denna's place was very comfortable and provided plenty of space for our girlfriend reunion. It is conveniently located close to Valparaiso University where we enjoyed reminiscing and catching up on new developments there. We also spent a day walking around downtown. Great reunion!

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.

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.

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.