Family-friendly vacation rentals in Matteson

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Popular amenities for Matteson family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in West Town
4.85 out of 5 average rating, 313 reviews

Lux Urban 3BR/3BA Duplex + Parking!

LauraRating, 5 stars1 week ago
Our host was extremely tentative and helpful. We really enjoyed our stay at the home. It was big enough to accommodate our family plus a few other visitors, plenty of beds, plenty of living space so people didn’t have to be on top of each other. Very close to downtown and the blue line which made going to the airport and downtown much more accessible. we didn’t even have to rent a car.
Home in Miller
4.55 out of 5 average rating, 132 reviews

Smart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities

TimothyRating, 5 stars3 months ago
Excellent location, great space, responsive host.
Apartment in Bronzeville
4.33 out of 5 average rating, 24 reviews

Spacious 2bdm unit 15min to Dwtn

Helena ORating, 5 stars3 months ago
This place was extremely great! It was close to downtown and lots of restaurants and food near by the bnb! Only thing I’ll say is the shower head is kind of flimsy but besides that everything is nice clean and the rooms are huge! Very peaceful and quiet over there!
Condo in Andersonville
4.89 out of 5 average rating, 9 reviews

Bright and Beautiful Penthouse - Close to the lake

GautamRating, 5 stars33 months ago
We had a great stay at Delphine's place in Uptown. The location is excellent, being on a tree-lined street, but very close to the Red Line, the Broadway bus, Andersonville, Little Asia, grocery stores and more. As we had a little kid, being right on top of the little park downstairs was also very convenient. On the flipside, it can get noisy in the summer with lots of kids/playgroups coming there, but as parents, we didn't mind. Delphine herself was very quick to respond via Whatsapp to all our queries before and during our stay. One thing to keep in mind at her place is that you are very much living in their home. If you are looking for an apartment that is only intended for guests, this is not it. While it is plenty big as a 2BR/2BA, it is full of stuff, furniture, photos, books, toys, etc. They have made a very nice office space in the main living area, but the drawback is that the living area is now very cramped. The main bedroom has 2 queen size beds in it, which is a bit weird, so we just ended up using one bed to keep our clothes on. The other bedroom with bunk beds is excellent for kids and more spacious. So overall, a great place and a great stay, and especially good if you are a couple with 1 or 2 kids. Just a bit cramped and crowded with stuff. We stayed for 2 weeks.
Guest favorite
Cottage in Valparaiso
4.93 out of 5 average rating, 411 reviews

The Lake Escape -Cozy Lakefront Cottage Valparaiso

KimberlyRating, 5 stars6 days ago
My daughters and I celebrated Easter at Kim’s cottage It’s clean, beautifully furnished and she is extremely responsive (I mentioned I forgot OJ on the phone and she was in the area and she left two OJs at the door) The cottage is cozy and fun We grilled, dyed eggs, watched movies, played a board game and loved the hot tub It’s clean clean !!! Just book it It’s a jewel box
Home in Miller
4.54 out of 5 average rating, 162 reviews

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

NicoleRating, 5 stars3 weeks ago
10/10 recommend staying here if you’re looking for a place 45 minute drive into Chicago. Hot tub was the perfect addition. Would definitely stay here again
Superhost
Home in Beverly Shores
4.91 out of 5 average rating, 133 reviews

Dunes Vacation Rental

DaveRating, 5 stars8 months ago
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.
Top guest favorite
Condo in Logan Square
4.98 out of 5 average rating, 270 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

DawnRating, 5 stars1 week ago
What an unbelievable find! This garden apartment is an 8 minute walk to my daughter’s apartment! I was looking for a place close to hers for a weekend visit. This place was perfect and it had a garage to park my car in! The interior was pristine. Beautifully decorated, the bed was comfy, big beefy towels for the shower, and you wanted for nothing! This place was fully stocked with necessities! I would recommend this place to anyone looking for an extremely nice stay in a great neighborhood with the added security of a garage to park in! Oh and there is a nice patio in the back yard if you want to sit outside on a nice day and relax! I will definitely be coming back the next time I come to visit! Thanks Bryan!

Family- and pet-friendly home rentals

Guest favorite
Apartment in Logan Square
4.9 out of 5 average rating, 396 reviews

Sunny Logan Square Artists' home

TerriRating, 5 stars1 month ago
Kyle's apartment was a visual feast, with fun and eclectic decor, furniture, and artwork! The listing states some quirks, which was accurate, but nothing that diminished the quality of our stay (for our family of 3). We didn't have a long enough stay to enjoy the full kitchen and dining table much, but would be a well-supplied kitchen for preparing full meals. The shower had some quirks but luckily Kyle even prepared a Youtube video to show and describe exactly how to turn on the shower. Part of the quirks of an older apartment building is radiator heating, which gives some 'clanking' and other annoying noises at times, so if you're noise-sensitive that's something to keep in mind. Kyle's local guidebook was helpful (unfortunately too long of waits at the places we had hoped to try) but found other options in the area for dinner. Our family of 3 had plenty of space for sleeping and lounging. This is a really cute space in a great location and a good close to downtown spot.
Guest favorite
Guest suite in Portage Park
4.94 out of 5 average rating, 157 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

JulieRating, 5 stars1 week ago
Jamie’s place was a perfect spot to stay in Chicago. There is access to the L within a few miles (with parking structure), and there are many walkable places locally. We highly recommend Caesar Pierogis on West Irving (offers gluten free pierogis). The neighborhood is charming and safe for walking. After long days of exploring, we came back to Jamie’s place and enjoyed watching Netflix and relaxing in the living room. The kitchen is stocked with utensils, and there is a grocery store within walking distance. Jamie is a very thoughtful host, and her home is quite accommodating. We had a lovely get away. Thank you, Jamie!
Guest favorite
Townhouse in Old Town
4.85 out of 5 average rating, 169 reviews

Downtown Elegance ✨ Private Yard Parking

JohnRating, 5 stars3 days ago
Alex was great at communicating and following up. We had some questions and she was responsive. Also goes beyond expectations on things like forgetting coats :0) - thank you! The location is great. Short walk to a Main Street of bars and restaurants, kid friendly too - happy campers pizza joint was a great reco! Also close to the brown line train station and not too far into town - we walked it with children and it was fine. House is really large, spacious. I know some have mentioned about hearing the train, but that is part of city living, it was more than fine. Enjoyed the stay, would recommend it and would go back again if visiting Chicago. Thanks Alex!
Top guest favorite
Apartment in Andersonville
4.93 out of 5 average rating, 429 reviews

Andersonville Living

ChristyRating, 5 stars1 week ago
We 3 loved our stay at Joseph and William's place! The apartment was clean, bright, and filled with art. The kitchen was lovely, the beds were all comfortable and the shower was very hot. We loved the back deck, and I imagine it gets used so much in warmer weather. The location is perfect. We walked to restaurants and shops in Andersonville. It was just minutes from Loyola Univ. which is why we were in town.
Guest favorite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 337 reviews

a SIMPLE place

KaitlinRating, 5 stars3 days ago
This is the 2nd time I've stayed here, and it is always exactly what I need. The space is great, the neighborhood is safe, and there's a Lou Malnatis and Portillos within a 15 min drive. Will definitely stay again!
Guest favorite
Apartment in Irving Park
4.94 out of 5 average rating, 237 reviews

Cool and Modern Chicago Apartment near Transit

AlexanderRating, 5 stars2 weeks ago
Definitely a great weekend! The look, and feel of the place was very comforting, and had a great flow. Design was tasteful, and anything that was needed was right where you’d expect it to be! A definite recommend!
Top guest favorite
Apartment in Logan Square
4.95 out of 5 average rating, 509 reviews

2nd floor of 1908 brick two-flat in Logan Square

KathlynRating, 5 stars6 days ago
Thank you for sharing your wonderful space. It was perfect to spend time as a family while moving our daughter in Logan Square. The park nearby was so easy to manage for our dog who joined us. Paul was responsive and helpful. Got to meet his pup who was adorable. Will definitely stay here again
Top guest favorite
Guest suite in Miller
4.96 out of 5 average rating, 355 reviews

Miller Mermaid Suite-100 yds from the beach!

PeterRating, 5 stars2 weeks ago
The place was beautiful and very close to the lake. Jennifer and Gary are great host and thought of every need a person could have while staying at their place. I would stay here again!

Family-friendly home rentals with a pool

Home in Michigan City
4.67 out of 5 average rating, 6 reviews

Dog Friendly Golf Cart included in Beachwalk w/ Po

KyleeRating, 5 stars35 months ago
Loved it! Awesome for kids and adults. Location is awesome and the house is beautiful.
Apartment in The Loop
4.76 out of 5 average rating, 216 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

LauraRating, 5 stars6 days ago
Fantastic location, felt incredibly safe, and was exactly as described. Great space and made for the perfect spot for our family during our stay in Chicago. Would absolutely return.
Home in Michigan City
5 out of 5 average rating, 11 reviews

Beachwalk Resort - Kid Friendly w/ FREE Golf Cart

HeatherRating, 5 stars8 months ago
Beachwalk Resort was a great place for families! The Anchor house was beautiful and although the fridge was broken, management worked to get a replacement and reimbursed us for the groceries we lost. That was the only issue we ran into! Overall, a lovely home with lots of space and an absolutely amazing kitchen. Would love to return one day!
Cabin in Union
4.5 out of 5 average rating, 4 reviews

Trailer- Rental Unit

KarissaRating, 5 stars21 months ago
Absolutely loved staying at Sylvia's! The camper is very conveniently located within the park - close to all the amenities and activities! Easy to access, beautiful grounds and a very peaceful stay for my family and I.
Superhost
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars8 months ago
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!
Apartment in The Loop
4.63 out of 5 average rating, 60 reviews

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

ParitoshRating, 5 stars4 months ago
I had an amazing stay at this place. Felt like home.The space was clean, beautifully decorated, and thoughtfully equipped with everything I needed for a comfortable visit. The host was incredibly welcoming and responsive, making sure every detail was perfect. The location was ideal, close to local attractions yet peaceful and quiet. It truly felt like a home away from home, and I can’t wait to book again for my next trip. Highly recommended!
Home in Michigan City
5 out of 5 average rating, 9 reviews

Pet Friendly in Beachwalk Resort - Walk to Beach,

AhmerRating, 5 stars10 months ago
Phenomenal option for vacation!!! Beautiful home thats 5 minute walk to a beautiful beach on Lake Michigan. Lots of things to do for family, including a pool, small lake swimming, fishing, shuttleboard, pool table, ping pong, kayacking, stand-up paddle board, movie room, basketball court and tennis court!!! I'm sure I'm missing a bunch of things. Oh and coffee shop with snacks too on the ground. The homes are beautiful and well-taken care of. Kids told me they want to come back next summer!!! Indiana Sand Dunes is also just a 15 minute drive to the east end of the national park.

Quick stats about vacation rentals that are family-friendly in Matteson

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ441 before taxes and fees

  • Total number of reviews

    310 reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Hidden Manna Cafe, A. Fusion, and Bocce's Bar and Grill

Destinations to explore