Family-friendly vacation rentals in Dundee Township

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Dundee Township

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in West Town

4.96 out of 5 average rating, 338 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Guest favorite

Apartment in Evanston

4.94 out of 5 average rating, 140 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 18 min walk for trains to city, 5 min drive to lake. Wifi

Top guest favorite

Apartment in Kenosha

4.93 out of 5 average rating, 242 reviews

Cheerful Apartment in Downtown Arts District

Cheerful apartment in newly renovated building above Professional Acting Studio at edge of Kenosha's Downtown Arts District. Near Harbor, beach, 4 museums, art galleries, live entertainment, eclectic restaurants, diners, coffee shops, Trolly, bike paths, parks, lakeshore, antique stores and specialty shops, Prime Outlets, Bristol Renaissance Faire, Great America. Metra Line to Chicago, close to Milwaukee. My place is good for couples, solo adventurers, business travelers, friends and families.

Guest favorite

Apartment in East Rogers Park

4.84 out of 5 average rating, 211 reviews

Cozy Northside Apt near Transp&Beach&Free St Prkng

PRIVATE Entrance, One Bedroom Apt w/ LVG RM near Lake Michigan in beautiful, residential & diverse neighborhood. FREE on street PARKING, OR driveway spot for Addt fee. Sleeps up to 6. *It has a Kitchenette, Full Bath, WiFi, Cable TV, in unit W/D. Close to METRA TRAIN (1 block & 18 min to loop/city center), Bus Stop 1 block & the CTA "L" (elevated) Red Line to City 7 blocks away. Enjoy our proximity to Public Transit, Beaches, Loyola & NW Universities. Great for family, friends & kids.

Top guest favorite

Apartment in West Lake View

4.98 out of 5 average rating, 244 reviews

North Side Near Wrigley Lakeview Walk Everywhere!!

Located on a beautiful tree lined street one block from the thriving Southport Corridor, one of the hottest neighborhoods in Chicago. You'll love the convenience of being just steps from the Southport Brown Line "L" Stop, you can see the City without ever needing to drive. Steps to outstanding restaurants, bars and shopping. Going to Wrigley Field? Enjoy a 10 minute walk down some of the most beautiful streets in Chicago. Ideal for families seeking comfort, style and a convenient location.

Superhost

Home in Kenosha

4.92 out of 5 average rating, 271 reviews

Where Family & Friends Gather to Create & Remember

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

Guest favorite

Apartment in Logan Square

4.95 out of 5 average rating, 693 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

Guest favorite

Condo in Wicker Park

4.83 out of 5 average rating, 339 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Guest favorite

Cottage in Fontana-on-Geneva Lake

4.98 out of 5 average rating, 103 reviews

Fontana, Wis, Lake Geneva 4bd 2.5ba Abbey Springs

4 Bedroom 2 1/2 bath vacation cottage in Abbey Springs Resort Community on Lake Geneva. Resort Pass is required for all guests (included) and gives entry to the resort plus indoor and outdoor pool (Memorial to Labor Day), hot tub, games room , gym, tennis courts , pickle ball. 2 restaurants beach and fire pit on site. Newly Renovated Golf Course not included but available by paying at club house . We welcome all .

Top guest favorite

Guesthouse in Batavia

4.91 out of 5 average rating, 293 reviews

Quaint Batavia Coach House

The Coach House is located behind our house. It is a private and separate little house. It is located close to the river path and lots of restaurants. The upstairs is one big room that has 1 queen and 2 twin beds. The upstairs also has a full bath. The TV in main living area on first floor is not hooked up to cable, but you can log into all of your apps and have access to news via YouTube TV, Netflix, Prime etc.

Superhost

Chalet in Williams Bay

4.88 out of 5 average rating, 249 reviews

The Bay Chalet

Featured in "At The Lake" Magazine in 2022! Enjoy the Northwoods of Lake Geneva! Just a 2-minute drive to Pier 290, Williams Bay public beach on Geneva Lake, lakefront park, boat launch and restaurants. 10 minutes to downtown Lake Geneva. 20 minutes to Alpine Valley. Enjoy Lake Geneva life while being tucked in the woods with a roaring fire in your cozy log cabin.

Guest favorite

Apartment in Lake View

4.9 out of 5 average rating, 183 reviews

Clean, spacious, walk to Wrigley! Self check-in!

Park your car and forget it- or just leave it at home! Charming 3 BR first floor apartment in a Victorian building in the ultimate location, perfectly situated between Wrigleyville and Lincoln Park in the beautiful, vibrant Lakeview neighborhood. Guys seriously… this is the ideal neighborhood for a Chicago getaway or visit with family.

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What guests are saying

Family Friendly 3BR Duplex in Roscoe Village

4.85 out of 5 average rating, 266 reviews3 weeks ago

John was a very kind and responsive host. Answered any questions we had very quickly. Home was exactly as pictured and described. Very comfortable place to stay. Everything was clean. Appreciated the family and kid friendliness of the home--not a lot of decorative items in reach that could be broken, no tables with sharp edges, low bed in the upper guest room that was easy to get in and out. Location was close to several restaurants and grocery stores, and not too far a drive from all the major tourist attractions.

Apartment in North Center

What guests are saying

Large sunny 3BR apt. in downtown Oak Park

4.92 out of 5 average rating, 182 reviews1 month ago

This was a beautiful place! it had everything we needed. Oak Park downtown is walkable and has everything you could want. It is an upstairs unit so be prepared for some steps. Parking was easy. Michelle was great! Downtown Chicago is only 15m (if there's no traffic.). We would definitely come back!

Apartment in Oak Park

What guests are saying

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

4.95 out of 5 average rating, 509 reviews6 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

Apartment in Logan Square

What guests are saying

Downtown Geneva Street Getaway

5 out of 5 average rating, 240 reviews3 weeks ago

Steve and his wife were extremely hospitable. The place is clean with nice decor. Plenty of space and the linens and bedding were fantastic. They thought of every little thing and the amenities they provided really went above and beyond. My husband, 16 month old, daughter and I felt right at home! Also, you can’t beat the downtown location! Can walk to literally everything downtown Lake Geneva has to offer!

Apartment in Lake Geneva

What guests are saying

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

4.93 out of 5 average rating, 204 reviews1 week ago

The hosts were very responsive to any questions. They live in the same building and helped with any concerns right away. The space was very homey and comfortable, with convenient bus stops nearby. There were plenty of books, movies, and games if you have time to kill at the apartment. You can hear a lot of footsteps from upstairs neighbors, but usually it wasn't too loud and the provided earplugs were helpful. The neighborhood felt safe and family-friendly. It felt like we were staying with good friends. We highly recommend this place and would stay there again.

Apartment in Lake View

What guests are saying

2 Miles to MDW 11 Miles DTWN Free Parking Wi-Fi

4.92 out of 5 average rating, 245 reviews3 months ago

I had an issue with the lock (my fault completely, not hers), and she was WONDERFUL to help me work through it and get us in quickly. LaWanna's place is hands down the AirBnB with the MOST amenities out of all the places I have stayed. In most places you have to bring your own toilet paper and paper towels after using a starter supply of tp. They had absolutely everything that we needed: a very well stocked kitchen, complete with creamer for coffee, syrup for pancakes, all the pots and pans you need, along with all the utensils, etc. The bathrooms were stocked with individually wrapped toothbrushes and lots of other toiletries in case you forgot yours. Seriously, it is very evident that LaWanna puts a lot of thought into her place and really wants her guests to be comfortable.

Apartment in Garfield Ridge

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