
Family-friendly holiday rentals in Northwest Indiana
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Top-rated family-friendly rentals in Northwest Indiana
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Family-friendly home rentals with a hot tub

Lux Urban 3BR/3BA Duplex + Parking!
Great stay! Thanks for making it so easy. Big space for lots of family to be together and have space.

The Getaway - Hot Tub - 3 BR 1.5 Bath
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!

B's Retreat: Hot Tub & 10-min walk to Beach!
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!

Beautifully eclectic Sawyer cottage
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.

Private Retreat w/Hot Tub - Beaches & Wine Tours
This was a very nice home for our large family of eight adults and nine children for a four night stay. A five minute drive to Weko beach, a beautiful sandy beach on Lake Michigan. We enjoyed visiting the farmer's market, one mile down the road on Sunday, open from 9 a.m.-early afternoon. Mikey's drive-in, serving burgers, fries, ice cream, etc., is directly across the road from the property. The very large back yard with hot tub and fire pit was a bonus. On the couple of occasions that I emailed Rebecca with a question or comment during our stay, she was very promptly responsive. Our family would stay at this property again.

Blueberry Fields/ House and Retreat
Very peaceful to stay put here--bring what you need and stay in these beautiful surroundings among birds and gardens and an art-filled home. Or spend time on nearby beaches and trails, wander the nearby small-town shops and nice variety of restaurants and look forward to a hot tub soak and campfire. Donna's home is welcoming and inspiring!

Debs Michigan hot tub house, open all year
Thank you so much for opening your beautiful home to us for our getaway trip. It was the perfect place for an out of town trip. I’ll definitely be recommending your place to friends, and I hope to return in the future.

Urban Luxury 1BR/2BA Logan Square Condo w/Garage
We had a great stay in Logan Square. The location has walkable access to the Blue Line making downtown easy. While this is a lower level unit, this does not feel at all like your standard “garden level”. It was full of windows and bright. Furniture was very comfortable. Bathrooms well appointed with amazing shower pressure. The bedroom is so quiet you get a great nights sleep. Bonus points for lamps on BOTH sides of the bed. The closet had high quality hangers plus good storage. The kitchen has everything needed for cooking or for storing leftovers from fabulous restaurants in area. The garage is a great bonus. Our young adult children live in the area and it was prefect for them to come over, hang out and visit with us. We spent time outside in the garden area with the fire table. Bryan was very responsive and helpful through our four-night stay. We will be back!
Family- and pet-friendly home rentals

Home newly remodeled minutes from Notre Dame.
How can I put in a few words how we felt about Cary’s house! We loved it immediately, everything outside, everything inside! Absolutely NOTHING was missing. Anything you needed was waited for you to need it. The house is meant to please the pickiest folks . You can’t name a thing that was a disappointment. Where else will you find a garden just waiting for you to pick it??

Stylish Studio in Historic Logan Square
Liz and Martin did a great job providing clear instructions for check in and the place was exactly as described. The room was very clean and provided a lot of privacy. Great location and is convenient to the subway and the area has a lot to do.

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK
Jamie was a really amazing host! She was friendly, helpful, caring and went over and beyond to make sure me and my kids were comfortable and had everything we need. Gave us lots of great recommendations to restaurants and as a first timer in Chicago she made sure I was aware of the traffic and other helpful information! My kids LOVE her she was vey nice, patient and gentle with them. Kid friendly house/area VERY quiet. The beds are the BEST after a long day of traveling very comfortable. The place was beautiful very nice decor and nicely maintained. We will definitely be staying here on our next visit to Chicago.

The Deer Suite
Private little oasis. The exact stay we needed. During a long road trip.

Best Deal In Michigan City 1.3 miles to Beach
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!

Berwyn Musical Apartment
Had a great experience, Kara the host was extremely kind and responsive with my questions and the place listed was exactly as it looked.Overall had a great stay!

Artist's Home, private level in quiet neighborhood
Gay’s place was wonderful. She is super nice and she gave great recommendations. Her place was great and the bed was very comfortable. I would 100% recommend staying here.

GERMAN HAUS Individual Rental
Linda is a great host! Fast responder and answered any questions I had, incredibly nice and welcoming! Such a peaceful and quiet stay!
Family-friendly home rentals with a pool

Union Pier Home With Private Pool!
My family loved staying here! The house was very cozy and it was great to have some games and kids toys for my daughter to play with. We were celebrating my parents 40th anniversary and it was such a great touch to have a polaroid camera in the welcome items to capture memories of our trip! We also loved the local bakery down the street, everything was delicious and nice to walk to.

Dunescape Beach Retreat, Downtown New Buffalo
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.

Beautiful RETREAT in the country
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!

After Dune Delight in Sun Coast Park
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.

Beautiful home with Beach views in Beachwalk
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!

Pool House On The Lake
This place was amazing for our family vacation. The goal was to spend family time together & there was plenty for us all to do. Lots of outdoor activities in nature! The beach was great for adult hang-out & games of spike ball (which we brought), & fun in the sand for the kids. Loved our pontoon boat rides & campfires as well. The indoor pool was great anytime day & night & was always a good back up in case it we had rain. The common areas were large enough for us to all have space & there was plenty of sleeping room. We had an amazing time & will definitely revisit. Ryan was courteous & quick to respond. Absolutely loved this trip!

Designer Cottage Relax Beach Pool & Spa—Windjammer
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!

Perfect Get Away - Private Hot Tub - Lots of Room
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!!
Destinations to explore
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
- Chicago Cultural Center
- Medinah Country Club