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Family-friendly holiday rentals in Grayslake

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Grayslake

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

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Top Guest favourite
Apartment in McHenry
5 out of 5 average rating, 151 reviews

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

Superhost
A serene bedroom is highlighted by a spacious bed with a light-colored duvet, flanked by large windows adorned with soft curtains. A contemporary artwork piece with gold accents is displayed above the bed, while a cozy armchair is positioned nearby.
Apartment in Grayslake
4.81 out of 5 average rating, 116 reviews

Historic home in quaint Grayslake, self check-in

Nestled in the heart of the historic village of Grayslake, this well-appointed flat, with brand new furnishings, linens, amenities, and a newly-renovated bathroom, is within easy walking distance to the restaurants, breweries, wine bars, coffee shops and the beautiful shoreline of Grayslake. Great Lakes Naval Base (11 miles), Six Flags, Fox lake, and other Chicagoland attractions are a short drive away. Multiple Metra lines to downtown Chicago and O'Hare are close. 10% Military family Discount.

Top Guest favourite
Guest suite in Zion
4.9 out of 5 average rating, 228 reviews

Nonsmoking, no cleaning fees, mother-in-law suite.

25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 8PM.

Guest favourite
A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.
Guest suite in Riverwoods
4.95 out of 5 average rating, 430 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Top Guest favourite
A welcoming living area is showcased, featuring a comfortable seating setup with a gray armchair and a round coffee table. Soft light filters through sheer curtains, illuminating the space. An intricately designed wall decoration adds an aesthetic touch beside a black bench with decorative elements.
Apartment in Beach Park
4.97 out of 5 average rating, 428 reviews

J’s Farmhouse Cottage. 2 bedroom duplex.

Formerly known as Magnolia Farmhouse inspired. 2 bedroom duplex. Experience the best of the midwest! Enjoy a newly remodeled, "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 miles from Milwaukee, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! We are minutes away from the Great Lakes Naval Station (9 mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge.

Superhost
A tranquil evening scene showcases a hot tub on the deck, with two glasses positioned on the edge. The vibrant sunset casts warm colors over the lake, reflecting off the water where a pier extends into the distance. Soft grassy areas are visible in the foreground.
Home in Ingleside
4.89 out of 5 average rating, 155 reviews

Chain O' Lakes Nautical 2/2 Lake House w/ Hot Tub

Welcome aboard First Mate’s Retreat! Unique and cute 2 bed / 2 bath nautical lake house has the best views of the Chain O' Lakes. Be amazed on the walk out lake view wood deck in the back yard, and watch sunsets fall over the bay and color the sky. The back patio is a great place to relax, entertain & relax. Fish or dock your watercraft at our pier if needed. There is a 4-5 person hot tub on the back deck for you to relax and unwind (Hot tub included in the price on this property).

Superhost
A charming two-story lake house is presented, featuring a prominent American flag and a large white flag. A spacious veranda overlooks the fenced yard, while bare trees frame the house against a bright blue sky with scattered clouds.
Home in Round Lake Beach
4.89 out of 5 average rating, 223 reviews

Corner Lakefront Property

This unique place has a style all its own. This corner lake house comes with a huge fenced-in yard, as well as a balcony off of the master bedroom and 2 parking spots. We offer 3 kayaks with life jackets, 1 paddle board, paddle boat and fishing poles, fire pit, outdoor and indoor games. We have 3 bedrooms with beds included, as well as a futon couch a trundle bed and a pull-out couch bed (6 potential beds total). This comes with 2 TVs, fireplace, WiFi, bar, new fridge and more.

Top Guest favourite
A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.
Home in Round Lake Beach
4.99 out of 5 average rating, 167 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Guest favourite
A charming bungalow exterior presents a warm facade with well-maintained landscaping. Features include a welcoming front staircase with wrought iron railings, potted flowers under large windows, and a flag hanging from the porch. A lush green lawn surrounds the home, enhancing its inviting presence.
Bungalow in Mundelein
4.88 out of 5 average rating, 227 reviews

Quaint Bungalow, near Great Lakes Naval Base

This cozy bungalow is located 41 miles north of Chicago; 60 miles south of Milwaukee, WI; and just 12 miles west of Great Lakes Naval Base. Nearby train stations make Chicago just a 45-minute train ride away. O'Hare Airport is a 30-40 minute commute from our home. Additional nearby sites include Great America, and shopping venues--from outlet malls in Gurnee and Kenosha, to quaint downtowns, like Libertyville. Location makes this home an ideal venue for Midwest sightseeing.

Guest favourite
Apartment in Waukegan
4.95 out of 5 average rating, 116 reviews

Cozy 1-Bed + Air Mattress

Step into comfort in this thoughtfully furnished 1-bedroom apartment in Waukegan, Illinois. Perfect for business travelers, visitors, or those in between moves — this unit hits the sweet spot of style, function, and value. The Space One bedroom with a full/queen bed plus an air mattress (for extra comfort or guest flexibility) Bright living area with seating, smart TV, and workspace Fully equipped kitchen (stove, refrigerator, microwave, basic cookware & utensils)

Superhost
A cozy bedroom features a black metal bed frame adorned with soft pillows in pink and green hues. Textured white bedding is spread across the bed. Natural light filters through the large windows, complemented by light-colored curtains, and a nightstand sits beside the bed.
Guesthouse in Lake Forest
4.8 out of 5 average rating, 117 reviews

Designer's Dream in the North Shore!

Welcome to the newly designed cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and parks. A cozy retreat in the wintertime to snuggle up with a great book and hot cocoa. It's also a perfect summer cottage for adventurers looking to take advantage of the beautiful landscape ! Check us out on: Instagram! longmeadowcottage

Superhost
A cottage exterior is showcased with a well-maintained wooden deck and black railings. A welcoming front door is featured, which is flanked by two windows. The surroundings include a manicured lawn with small flower beds, enhancing the cottage's inviting appearance.
Cottage in Antioch
4.83 out of 5 average rating, 114 reviews

#4: Cute 2 bedroom cottage on the beach!

Come relax at Turtle Beach Marina! Rent a Pontoon or a Kayak. Spend the day at the beach and at the beach bar (Beach bar is open mid May until the last weekend in October). There is a restaurant and gaming room (slots) on the property. Quaint cottage has 2 bedrooms with a full bed in each. Up to 4 people allowed. There is no oven but has a 2 burner electric cook top. A grill is also available. Beach themed cottage is completely remodeled. 💜

Popular amenities for Grayslake family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Grayslake

  • Total rentals

    20 properties

  • Nightly prices starting at

    $123 AUD before taxes and fees

  • Total number of reviews

    680 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi