Family-friendly holiday rentals in Waukegan

Cozy 2 bedroom home with a study

This newly remodeled chicken Coop turned into a 2 bedroom A frame home is fifty miles from Milwaukee, forty-seven miles from Chicago, and ten miles from the Naval Station. We are a couple minutes away from City of Hope, Six Flags Great America, Bristol Renaissance Faire, Great Wolf Lodge, Casinos, and the beach. There is also a Target and Starbucks down the road, what more can you ask for! The stairs to the bedrooms are steep and narrow so please be careful. Please enjoy the home to yourselves

Family · Kitchen · Hospitality

*Entire house w/4 LG Bedrms, NAVY 4 miles/baseLake

We are excited to welcome you to this clean and spacious home/perfect location.10 mins /4 miles from Great Lakes. SLEEPS 5- 12!! A"Gathering Place" is for FAMILIES! Stay all together in one place and make memories! Waukegan has parks/cool pl! A Dock/ lakefront, galleries, breweries, restaurants, and more! Near the train station, if you want to travel to Chicago N Suburbs. Close to Six Flags, the Genesee Theatre and the new CASINO! The train is 2 blocks/travels to both Chicago and Wisconsin.

Family · Indoor spaces · Nearby

"Magnolia Farmhouse" inspired 4-bedroom home

Enjoy a spacious, open floor plan on a quiet, dead-end street! This "Magnolia Farmhouse" inspired 4-bedroom ranch home is set on one acre. Located 50 miles from Milwaukee, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! Minutes away for the Great Lakes Naval Station (9mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here, make Boyce Lane your home away from home today!

Kitchen · Indoor spaces · Quiet

Kalo House | Mid-Century Modern Retreat

A beautifully preserved mid-century modern home designed by noted architect Edward Humrich. The Kalo House blends iconic architecture with warm, curated interiors. Clean lines, expansive windows, and thoughtful design throughout. Peaceful and stylish, it’s the perfect retreat for design lovers visiting Chicago’s North Shore, Lake Michigan, or nearby Great Lakes Naval Station. Thoughtfully, curated and hosted with care…Perfect for Navy graduation stays and gathering families together.

Kitchen · Indoor spaces · Condition

Navy Graduation Retreat- 4BR Home by Great Lakes

Wonderfully remodeled multi-level home ideal for Navy Bootcamp Graduation stays and family visits, located between Chicago and Milwaukee. With four true sleeping areas (3 BR/2 BA upstairs plus a private lower-level BR/BA), the home is well-suited for multi-generation comfort. Features include a large yard backing to a golf course, game room, screened porch, and seasonal in-ground pool (weather permitting). 📍 8 miles from Great Lakes Naval Base | 📍 5.5 miles from City of Hope – Zion

Indoor spaces · Kitchen · Nearby

Historical Hideaway near Naval Base

Step back in time at The Pilothouse, a charming historic 1854 home located in Waukegan’s historical district, just 12 minutes from Naval Station Great Lakes. This beautifully preserved home features Navy and aviation-themed décor, 3 cozy bedrooms, a sunroom filled with lush plants, a fully equipped kitchen, and a spacious backyard with a gazebo, large patio, and grill—ideal for relaxing outdoors. Experience the perfect blend of vintage charm and modern comfort in this serene retreat.

Kitchen · Indoor spaces · Comfort

Spacious 2-br, 1 bath home w/AC near Naval Base

Welcome to our cozy and comfortable Airbnb, perfectly located near Naval Station Great Lakes (approximately 5-7 min., 2 miles), Six Flags Great America, and just an hour from downtown Chicago! Whether you're visiting for Navy graduation, family time, business, or a weekend getaway, our home offers the perfect balance of convenience and relaxation. We take pride in providing excellent hospitality and a smooth, stress-free experience from check in to check out.

Indoor spaces · Family · Layout

King Suite | Sleeps 8 | Near Navy Base & Six Flags

Welcome to your peaceful woodland escape right in the heart of Waukegan! Backing directly onto a lush, private nature preserve, this freshly updated 3-bedroom, 2.5-bath home offers the ultimate blend of suburban convenience and serene privacy. Whether you are in town celebrating a Navy Boot Camp graduation, visiting Six Flags, or simply seeking a quiet family getaway, this 1,800+ sq ft retreat gives your group plenty of room to spread out, relax, and recharge.

Indoor spaces · Family · Comfort

Historic Downtown Libertyville Loft

Enjoy a stylish experience at this centrally-located 1600 square foot place. Located in the heart of Downtown Libertyville, half way between Chicago and Milwaukee. Close to Six Flags, Great Lakes Navy Base, Lake Michigan beaches, forest preserves, train station and the Chain of Lakes. Downtown Libertyville is a trendy town offering several restaurants, shops and fun events. Book one of the only units truly Downtown Libertyville.

Kitchen · Indoor spaces · Location

Great Lakes Naval Station-Waukegan- Gurnee-6 Flags

Under 10 minutes to RTC Great Lakes (Graduations) Under 10 minutes Rosalind Franklin University 15 minutes to Six Flags Affordable, private and comfortable... These are just a couple reasons why this is the ideal room for you to settle into during your stay in the area! Whether it be for boot camp graduation, the medical schools in the area or maybe you’re just passing through; book your stay while its still available!

Kitchen · Indoor spaces · Parks

Home Sweet Home, minutes to Great Lakes Naval Base

Home Sweet Home is located 35 miles north of Chicago; 53 miles south of Milwaukee, WI; and just 4 miles east of Great Lakes Naval Base. Chicago is a 45-minute train ride away. O'Hare is a 30 to 40-minute commute. Great America amusement park and shopping venues, including Gurnee and Kenosha outlet malls, are all within 20 to 30 minutes away. Location makes this home an ideal respite for Midwest sightseeing.

Kitchen · Indoor spaces · Checkout

Gurnee Gathering Place Near Navy Base

Centrally located less than 15 minutes to Navy Graduation, Gurnee Mills shopping and American Place Casino. It has a spacious first floor with tons of comfortable furniture for lounging around, watching TV and hanging out with friends and family. Upstairs has 4 bedrooms with 3 king and 1 queen bed to comfortably sleep 8 guests. This is the perfect place for a family gathering!

Indoor spaces · Family · Sleep quality