Pet-friendly holiday rentals in Chesterton

We loved the indoor mini golf lots of fun enjoying each other right from the comfort of the home.

This is our second stay in this home. Quaint, clean, and in the heart of New Buffalo. We loved that our dog could join us! Plenty of towels, linens, cleaning supplies, and amenities that made our stay comfortable. I highly recommend!

Donna is a wonderful host! The cottage was the perfect spot for a quick getaway—it had everything we needed for a relaxing stay. We especially loved the large, fully fenced-in yard for our dogs and the screened-in back porch, which was perfect for unwinding. The kitchen was beautiful and well-equipped, and the quiet neighborhood made for a peaceful retreat. Plus, it’s within walking distance to the shops and restaurants in Three Oaks, which was a big bonus. Be sure to check out Dreihart Wines and 6 Linden while you're in town, offering amazing German-style wines and a great selection of specialty groceries and imported foods. If I had to mention one downside to our stay, it would be that the beds felt a bit worn and not as comfortable as we’d hoped. That said, everything else about the stay more than made up for it, and I’m still giving Donna and her charming cottage a full 5 stars!

My wife, oldest son, and I were looking for a quick getaway that wasn’t too far of a drive from Chicagoland. My wife came across Deborah’s listing and immediately knew it would be a nice location where the three of us could stay and my son could enjoy fishing. The cottage was located steps from the lake and my son spent hours fishing from the dock. The cottage was very clean and was the perfect size for the three of us. I think the only downside was that there weren’t many dining options nearby. We ended up eating one breakfast and one lunch in Walkerton and had dinner in Plymouth. The kitchen at the cottage did have enough supplies to enable us to cook two perch that my son caught earlier in the day, however.

I loved this space! It was private, with beautiful surroundings, and a cozy and curated interior. Not your average air bnb in the best ways. We had everything we needed. Elena was a very kind host and offered clear instructions and great recommendations. Would stay here again :)

Igor's Prairie Home was the perfect backdrop for my husband and adult children to take a break and reconnect as a family. The home is beautiful and so comfortable. We enjoyed the great hot tub and sitting around the fire pit. Oh and I don't want to forget to mention the tree house! How clever 🌞. Location is perfect for anything you'd like to do in the area because the house is located with easy access to Red Arrow highway. Either way you go there is plenty to see and do. Everyone wants to stay at Igor 's again and my son in law has already recommended to his parents. So I know we'll be back. 😎⛱️

We stayed for almost a week with three dogs. Sarah's place was perfect for our needs - great backyard, comfortable beds, clean and equipped kitchen, and awesome location - close to Chicago, Indiana dunes and easy to navigate thru, no traffic. Sarah and her family (and their amazing dog Chandler) are super friendly and helpful. We will definitely stay there again once back in the area.

Crystal's place was clean and comfortable and had everything we needed. Crystal sent us all the information we needed for check in and responded to any messages very quickly. The house is very nice and lots of room. It had a lot of restaurants nearby and was a great place to stay to visit the Indiana Dunes. Would definitely stay again!

Host was very responsive and helpful. we enjoyed our stay and would definitely return. Kids loved the pool and outside area! Great location and the house is decorated very beautifully! The kitchen provides everything you need to cook a meal also.

We had a great stay! The house was perfect. It was nice and clean with a great rooftop deck and screened in porch. The location could not have been better, walking distance to everything in town. Everything was easy as far as check in and check out with a book explaining everything in the house. Mark was great at responding to questions. I would highly recommend staying here.

We absolutely love staying here, it is our go to staycation home. Lisa is always available if we need anything. This was our second stay and we plan to come yearly. Our kiddos love the pool and love how close stores and Dairy Queen of course are in walking distance :)

The location was so peaceful and close to everything (10 mins from the dunes). The house was comfy and had everything you could possibly need. Melissa thought of everything! The pool.. OMG the best! The heater made the water PERFECT! Made it even more special that we could bring our dogs. The fully fenced yard was perfect. Will definitely be coming back.

Amys place is beautiful,all we had to do is check in with our food and clothes,we needed nothing else place is amazing,returning next year!

We had a lovely family reunion at St Joe’s overlook. Kitchen came with literally everything- all sorts of cooking instruments (crock pot, air fryer, toaster etc), spices/oils, and zip lock bags for leftovers. All brand new appliances and ample prep space. We got the pool heated and it was wonderful! Very large size to fit all the family kids. The hot tub was a nice save for the adults who were freezing. Beautiful views from the living room of the river with ample and comfy seating. The home was perfect for a large gathering. We appreciate Evan and Claire hosting us they were always responsive and helpful.

Lovely home, many well thought out perks like fans in upstairs rooms and beach toys for kids! Info said it was an easy short walk to beach so I spent a whole lot more than I usually would. With children it would not be pleasant and is really not a short walk (and is on a semi busy road) & beach is down a whole lot of steps. BUT there are parking spaces so it was fine. Within the house, the steps are fairly steep at parts & there are 2?big ones going into house &!these were hard for my 70 year old mom w knee issues. So if person reading reviews is one of those people, this might not be THE place. That being said, it is very short walk to community pool & host is very responsive & house is beautiful! My mom mostly stayed within first floor including an awesome bed/bath on ground floor. There are games (although I didn’t love the Ouija board 🫣😂) . This would be a great place for multiple family / friends to split cost ;) Its very beautiful & community pool & hot tub are great!

This is our 5th year of vacationing in New Buffalo and have stayed at Missy's place on 3 of those visits! The house works beautifully for our family (7 adults and 4 kids under 6 yo) and you're never tripping over each other, which makes it so relaxing! We'll be back!!

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!

Perfect for our trip. We attended the Indiana Dunes Bird Festival. This place was perfectly located for all of our activities. Later this summer if we go up for a beach getaway we would stay again. Walkable to deep dish pizza too. Great host. Very responsive. Thanks for the great stay.

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 great 1 night stay here. It was just as described and the location is a very short walk to a coffee shop, the restaurants on the Main Street, and all the antique shops. Everything was very clean, the kitchen was well equipped, and very comfy bed.

A great stay close to the Dunes! We took the South Shore Line into Chicago and did the 3 Dune Challenge and both were great. Highly recommend this place.

we had a great a time

It was nice, the host is kind, and the location is peaceful. It's like an adventure. The RV is clean, and well kept, and has the best view of the tree and horses alike. Our mastiffs went up to look at the horses and they did not spook. The horses seem tame and happy. The RV also has a nice deck, and a swing for a great view of the sunset. The bed is very comfortable and check out is flexible, communication with the host is awesome. We accidentally took the key, and the host was very understanding of it. Peaceful spot at the end of the state street. Will def come back.

Probably the best place we've stayed. Clean, organized, and exactly as described. The attention to small details makes you feel at home. Will book again if we go back!