Family-friendly holiday rentals in Valparaiso

Great stay! Thanks for making it so easy. Big space for lots of family to be together and have space.

My wife and I and our twin 2 year olds stayed here over Mother's Day weekend. This home was perfect for us and had everything we needed as a family of 4! We really enjoyed all of the living space the home had to offer. From the front porch, to the 3 Seasons room, to the back deck. Our girls especially like the stoned area! They loved picking up the rocks and making piles lol. Don't forget the hot tub! It was super clean and we loved using it. The beds were super comfortable, and the bedrooms had everything we needed. A huge plus was having robes and slippers in every closet to use to go out to the hot tub! This location is at the end of a street and felt very private even though it was in a neighborhood. You are about a 2 minute drive to downtown Three Oaks. We would definitely stay here again. Also, Three Oaks is such a cute town and everyone was so nice! We can't wait to go back!

Easy check-in and felt right at home. Jennifer was always responsive to messages. She also gave great suggestions for food etc. The house is located perfectly for walking to the beach, market, restaurants, coffee. It is also a great location for quick travels to New Buffalo, Three Oaks, Michigan City and more. We will visit again for sure!

This is the second year I rented this place for my birthday weekend away with friends. The house has so many accommodations for sleeping and different sitting areas. However, the main event is the kitchen. My friends and I love to cook and that's why we came back a second year in a row. The kitchen is unbelievably well-stocked with anything you might need to cook. There are multiple sinks so someone can be cooking while someone else cleans. The layout is perfect for people to hang out with whoever is cooking. There are two ovens. It is a dream. The house feels comfortable and lived-in, and it feels like there has been a lot of thought and intention focused on the user-experience. Cannot say enough nice stuff about this house, cannot recommend enough. Will be coming back for my 29 birthday.

Rebecca saved our Memorial Day Weekend friends getaway! We ended up booking this home last minute due to some unforeseen circumstances, and it couldn't have worked out any better. The home is beautiful, Rebecca is extremely helpful and communicative, and the location is near restaurants, bars and wineries. Can't wait to stay here again!

Donna’s home was amazing!! We felt so safe, comfortable, and relaxed during our trip. I highly, highly recommend it for your girls trip!!

What a fabulous location! Walk to downtown and so many restaurants. The house had a great floorplan. Hot tub was a bonus. Terrific trip!

Very nice place right by the Indian Dunes; property is very nice with lots of great landscaping, outdoor furniture and open spaces. Outside had a large 8+ person hot tub, grill, upscale fire pit, nice landscaping/frog ponds, and lots of deck space/lawn space. House itself was very well appointed and clean -- worked great for our group (6 adults, 8 kids). Mark was quick to respond whenever we reached out.

This place was super adorable. My friends and I needed a weekend away and this was the perfect place. Everything was super clean. There’s coffee, teas, all sorts of cookware to use, it was just super easy. It’s the name on the board when you walk in was a great touch. Hope to stay here again soon and highly recommend!!

Our family’s stay at Anna’s Cottage was wonderful! Our son says his favorite part of vacation was the cottage! It was a great location that was walkable to downtown and the beach. We loved the amenity of having a washer and dryer. The only thing we think could be improved was for it to have a bigger washer.

I’ve been to Chicago many times but never to Wrigley Field. This place was amazing, just what we needed! It was faster to walk (20 minute walk) to and from the concert at Wrigley Field than to drive and park, taxi or Lyft. I communicated with the host about safety of walking at night. No problem. I had sent a message and he called me immediately. And also gave me recommendations on food and shopping that were spot on! We met locals and had a blast! The neighborhood is quiet and easy to park (but you do need to be able to parallel park and no one in the area drives big vehicles,.. only a few minute drive to downtown (Navy Pier area or take the L train for fast and cheap transportation without the hassle of parking). We were busy the entire time in the Chicago area so didn’t spend much time at the Airbnb but it was quiet, we slept great and just what we needed!

Had an amazing stay. Would definitely recommend. Very cool and unique spot.

Great stay. Liz and Martin suggested the farmers market down the street and was very impressed with it and brought some Chicago goodies back home with us . Property location was surrounded by decent restaurants. our room was nice and clean . we also hung out in the nice out door area right outside our door. nice and relaxing.

We had a wonderful stay and will definitely be returning! The house was beautiful and extremely clean, the master bed was so comfy and the backyard was perfect for our pup to run around in. The location was also perfect and in a peaceful area, but also only about 10 minutes to New Buffalo and some amazing restaurants! I would definitely recommend and can’t wait to book our next trip back here!!

Perfect little cottage for a weekend away from Chicago. Serene, cozy and well equipped with anything we needed. Would absolutely stay here again!

love staying in this cabin, is so cozy and warm. We spend a good day there . thanks for sharing this space with us

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.

It was a pleasure meeting Antoinette and her family. They are extremely welcoming. The property is amazing especially if you like horses, donkeys, chickens and outdoor cats. We definitely recommend a stay there.

Loved our stay. Right in the middle of everything we wanted to do in Chicago. If we couldn't walk to it, public transportation was readily available. Stephanie was always friendly and responsive. Would definitely stay here 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.

This Airbnb was so nice and so much bigger than we thought it would be! The first floor has a bedroom with a king bed and bathroom across. Upstairs has another room with a king bed and a room labels as an office but actually a double bed so plenty of private sleeping places as well as the loft area. The futon was very comfortable to sleep on too. It took about 10 minutes to walk downtown New Buffalo which was exactly what we wanted. The other direction had a local shop called The Farmette that you can drive or walk to - it was the cutest place to visit. While it was too cold for the pool when we were there, it is an awesome and convenient amenity and it’s right outside of the patio. We had 6 girls and more than enough room for a weekend stay. Would highly recommend!

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 !

We had a great time at the house. Was exactly as described and in the photos. Check in was extremely easy, and someone came out to meet us and give us a run-down on the property within a few minutes of being in the house. Tons of extra stuff to do around the farm area (pool, canoes, trails, etc). Had a great time staying there, and would definitely come back next time we're in the area.

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!