Pet-friendly holiday rentals in Chesterton

Cozy, fun little spot for an overnight! Great access to Michigan City, New Buffalo, Dunes, etc. Adorable dogs. Great vibes all around!

Overall great experience. The home was very clean and comfortable. Communication was great from start to finish. I would recommend and would definitely stay here again.

Peter was a great host, very responsive to all questions we had. Everything was as advertised.

It is the perfect place for our family with lots of space. We love the yard for the kids to be able to run around. It is also close enough to downtown to walk. Joe is very responsive and accommodating.

Great house and even better host. Would definitely stay again

Great place and as the description suggests, it’s pup friendly! We lacked nothing during our time there and would highly recommend.

Cozy place, friendly hosts, great communication, exactly as described.

House was easy to locate, great neighborhood, great location, and easy drive to where we needed to be. House was clean and had everything we needed. 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.

Sharon (and co-host Lauren) was a wonderful host! The home is beautiful, spacious, and charming. They even left a note and sweet treat for the birthday we were celebrating! Short walk to the semi-private beach was an added plus. We enjoyed the hot tub both nights we stayed, and would have enjoyed the pool if in season. Nestled wonderfully between New Buffalo and St. Joe- both full of little shops and restaurants.

We had a great stay!! The house was perfect for the five of us and our dog, with enough space for all of us to feel comfortable. The bathrooms were clean and the kitchen was well stocked. The pool was the best part! Melissa was super prompt when it seemed like the heat to the pool wasn’t running and we were back in there in no time - the heated water was perfect for this fall weather! We also tried some of the recommended spots and overall, this was exactly the quick getaway we needed!

I highly recommend staying at Kerilyn's farm house. My wife, a few friends and myself come to Baroda every year for my birthday to do the wine trail. This was our first time staying at Kerilyn's but definitely not the last. The home is beautiful, accommodating and located near some of the finest wineries in the area. The hot tub was fabulous and I couldn't ask for a better way to end the evening. Kerilyn was friendly, attentive and fast to respond. We're looking forward to our next visit. Thank you, Kerilyn!

This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10

The house was clean, comfortable and as described in the listing. I wouldn’t hesitate to book the property again. The heated pool and hot tub were great for our group to relax.

We met here with college friends and their families and had a wonderful time. There is a wide variety of books, games, and activities; we really didn’t need to bring our own! The hosts were very responsive and even drove out with trash bags when we messaged that we couldn’t find any. Highly recommend!

Beautiful house, very well thought out for guests. Host and Co-Host were absolutely wonderful through the whole process. Lots to do in the area. Would highly recommend!

We had the best time here! It’s so beautiful, the walk we took around the property was very relaxing, highly recommend if you want to be somewhere that is very peaceful. Dennis is a fantastic host, we hope to come back soon!

This is a beautiful house and Amanda has everything ready before our arrival. The house is clean and I just love the ecstatic. We have a lovely girl's night and would love to come back maybe a warmer summer time to check out the beach and outside. We were a little bit confused about the light switches though even Amanda already labeled everything.

Diana’s place was the perfect place for our family to gather and celebrate an up coming wedding. Diana greeted us when we arrived and showed us around the home. There was a large binder on the counter highlighting all that the area has to offer. The home was well stocked with everything needed to make our stay enjoyable. When I text Diana on day 2 of our visit about where to locate something, she responded within 3 minutes! Our 3 small grandchildren loved the stuffed horses, ping pong table and walking 3 houses down to watch the beautiful sunsets! We highly recommend book this lovely home the next time you find yourself in the Southwest corner of Michigan. I know we will 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!

Cute log cabin, a bit rustic, but it added to the charm. Portia was very responsive to questions & helpful.

My partner and I had such a lovely stay! The home was beautiful and gave off such a calming atmosphere. Check in was very simple and we felt right as home as soon as we entered! Kelly and George were also very communicative, friendly, and quick to respond. We will definitely be back!!

Great place to stay for ND Football games, we'l be back next year!

I choose to stay at Kathi's place for one night instead of getting a hotel room. It was exactly what I was looking for...peaceful and tranquil surroundings. Kathi was an amazing host. She met me outside and showed me around as well as telling me where the local grocery store was. Comfortable bed, sofa, and plenty of blankets. I wish I could have stayed longer. Would definitely book again.