House holiday rentals in Chesterton

My girlfriends and I had a great stay! Ann’s place was peaceful and beautiful. We enjoyed relaxing outside, watching the animals and soaking in the hot tub. We will definitely be back!

This house was so beautiful and was a perfect place to spend a girl’s weekend! Would recommend over and over again and would definitely stay here again! Mike was also very quick at responding (even on the weekend) and when something wasn’t right he was very quick it fix it.

Well-maintained house, spotless upon arrival, great view of the area from the kitchen. Ice machine was a great touch especially with a bunch of people in the house! Would definitely come back!

We all walked in and said WOW! It was beautiful and had so much charm. We have stayed in many rentals and this was by far the cleanest and most organized. We traveled with 3 couples and there was plenty of room to gather and socialize and room to just chill by yourself. The boardwalk made for a wonderful morning walk. Brittany was a terrific host answering any questions I had and providing a list of thing to do in the area. Certainly worth the money! We would definitely stay again. Rita

I recently stayed with a few of my girlfriends for the weekend here. My friends and I absolutely loved this place. It was in a picturesque setting, and we loved how cozy it was. We especially enjoyed having the hot tub, the access to the public pool with clubhouse, and being able to walk to the beach to see the sunsets. We were able to enjoy a fire every night within the fire pit and loved being near the woods and the pond. Kristen was extremely responsive and a great host. My girlfriends and I would definitely stay again. We absolutely loved it here! Location is perfect for visiting lots of restaurants, wineries, and enjoying the best of Southwest Michigan.

We had an amazing stay to celebrate a milestone birthday with my extended family! The house comfortably fit 4 families and a labradoodle and was excellent for the 5 kiddos. The heated pool and hot tub were fantastic for cooler than expected temperatures Memorial Day weekend and kept the kids entertained. We opted to cook and grill at the house and had everything we needed. The house is also super close to the beautiful New Buffalo beach. We will be back!

We really enjoyed our stay at Jennifer’s house! It was clean, great location & cozy! We especially loved the automatic pool cover so we could actually relax on vacation with our little ones running around. I also loved the three separate areas outside (pool, fire pit, grassy area). The separate areas offered a nice change of scenery to break up the day without leaving the house. I also loved that it’s a spacious ranch style house, so was easy to keep eyes on the kids. Jennifer was a wonderful & accommodating host & can’t wait to get back to her house soon! Thanks for having us!

Todd was easy to communicate with and the house was clean. Thank you! Pool was refreshing and everything was in working order.

Quaint, peaceful, perfect for a couple, overlooking a gorgeous lake. 10 mins drive to downtown. Great WiFi and thankfully no TV. Loved every minute. All amenities included. Would like to stay again.

Great location—just a few minutes from Indiana Dunes National and State Parks, and very close to a convenient travel center. Michigan City is also nearby for extra exploring. The backyard was a real highlight—peaceful and beautifully set up for families to relax and spend quality time together. Highly recommend!

This Airbnb was such a peaceful escape beautifully put together with so much intention. The overall vibe was serene and calming, which was exactly what I needed. One of my favorite parts was the screened-in porch perfect for enjoying the fresh air without worrying about bugs. I also really appreciated the sound machines in every room; it was such a thoughtful touch that made sleeping even more restful. If you're looking for a stay that brings peace and comfort, this is the place. Highly recommend!

Great house for the value! Clean and lots of amenities! Wish we visited in summer as fenced backyard is great! Stairs to second floor are steep but in good condition with handrail! There are local trains that are present throughout the day/night, but their sound didn’t bother us 😊 Overall a great value and lovely vintage home! Host was very responsive and friendly! Thank you!

Tiffany and John were great host! The house perfectly matched the description and was the perfect spot for a short weekend trip. The house was very homey and had everything you could need. The big yard was a huge plus as we had our dog with us! Tiffany and John were very responsive and very accommodating throughout our stay especially when we had to add another person to our reservation half way through our stay. I would definitely recommend staying here as it definitely feels like a second home!

This was a wonderful Airbnb. It was very clean and the decor was lovely. It was a short drive to Indiana Dunes State Park and restaurants in the area. Very convenient. We really enjoyed the heated pool and the dog friendly atmosphere. My dog loved the yard. Would 100% stay again if in the area.

Perfect location to The Dunes! The place was comfortable, clean and cozy for a family birthday trip for 12 people. Plenty of space for all ages. The property was private, large and beautiful. If we’re ever in the area again, this is where we’ll stay for sure. What a great trip!

We had a great time! Everything was fantastic! We had a couple bonfires that were so peacful and the firepit was pretty cool. The host was so quick to respond back for anything. The whole place was clean and had good strong coffee. ;)

We really enjoyed our stay at Chauna’s place! The Airbnb had everything we needed and we felt right at home. It was perfect for a girls beach trip! The host was very responsive and helpful. We’d love to come back some time. Thank you for hosting us!

Host was very responsive! Thought there was a problem with the central air (ended up not being-thankfully!!) so I messaged and had a response quickly! Liked that it was so close to the beach, zoo & splash pad!

Had the absolute pleasure of taking my wife to Rudy + Deanna's Airbnb to celebrate our first anniversary. Both co-hosts were very responsive, very friendly, and shared a ton of useful local knowledge for us to make our weekend special! The Airbnb itself was gorgeous - pristine inside with all the amenities you could need. The four of us (two dogs, yes they are pet friendly) had a wonderful time and would absolutely recommend this place to others wishing to visit Michigan City! Thanks again!

We had a wonderful time at the Porter house! It was as-expected and it had everything we needed. Proximity to the beach was amazing and the backyard forest was so magical. It felt very secluded but still close to everything. Would recommend.

Very comfortable, cozy home that was very clean and perfect for our overnight trip! Highly recommend!

Great place to stay while we were visiting our grandchildren for the weekend! It was nice to have the kitchen to make coffee and breakfast in the morning. Comfortable bed and private, quiet location. Thanks again!

The house was wonderful, incredibly clean, and offered a lot of small amenities.

Unbelievable responsive. We would stay there again. Everything we needed and more.