
Holiday rentals in Waukegan
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Top-rated holiday rentals in Waukegan
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Moss Point House-Navy Families Welcomed!
This unique house has a style all its own. Designed with cheeky fun but ensuring cozy comfort. We want you to relax into this beautifully renovated house. Whether you are a family in town for an event, a traveling professional, or on a friends getaway, this place is for you! We are centrally located. Near the interstate, Great Lakes Navel Academy, Gurnee Mills, Six Flags, College of Lake County, Abbott Labs, Baxter, 3 hospitals, 2 wedding venues, walk to the beach, explore the local town.

Charming 2Bd Townhome Near Beach & Base, Six Flags
Let your worries drift into the sunset at this bright 2bd/1.5ba duplex vacation rental close to Lake Michigan beaches, Great Lakes Naval Base, Six Flags and the Casino. Near hiking, golf courses so you can practice your swing, amusement parks and shopping at Gurnee Mills Mall. Once you’ve hit up your choice of big city attractions in Chicago, seen Navy Pier & the Bean, relax on the deck. Rental agreement, government ID, and security deposit hold required within 24 hours of initial reservation.

"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!

Designer luxury loft in perfect downtown location
Escape to our spacious and luxurious designer open-space loft with panoramic downtown views through our giant windows. Whip up your favorite meals in our modern kitchen with modern stainless-steel appliances and plenty of storage space. A cozy and comfortable bed, smokeless fireplace, and ample walk-in closet ensure a clutter-free and restful environment. Treat yourself to a rain shower in any of the two bathrooms, complete with luxurious features like towel and mirror warmers.

Chic Oasis/Game Room/Near Base
Welcome to your perfect getaway! This spacious 5-bed, 2-bath ranch house offers a cozy stay just 4 miles from Great America, The American Place Casino, and the beach, and 6 miles from the Great Lakes Naval Station. Ideal for families or groups. Enjoy a fully fenced yard for outdoor fun or pets. Inside, relax in the welcoming living area with plenty of space, plus a fully equipped kitchen for all your cooking needs. This home has everything you need for a memorable stay!

The Cardinal Nest
The Cardinal's Nest it's a walk-out basement, perfect for families and friends. We are located 18 minutes from Naval Station Great Lakes and just 5 minutes from City of Hope Cancer Center, and the Lake Michigan shoreline and nature reserve. Ideal for hiking and birdwatching. Only 20 minutes from Six Flags Great America and downtown Kenosha museums. 3 sleeping areas (Queen bed, Full bed, Queen sofa bed). Equipped kitchen. Private entrance with smart lock.

Cozy & Elegant 2BR | Near Naval Base and Six Flags
Experience refined comfort in our newly renovated 2BR retreat near Six Flags, Gurnee Mills, Naval Station Great Lakes, and Libertyville. Enjoy a king suite, queen bedroom, elegant walk-in shower, gourmet kitchen, and blackout shades. Traveling with a larger group? We offer multiple units in the same building so guests can stay together while enjoying private space. Other unit: https://www.airbnb.com/rooms/1307502918806762104

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!

Updated 1BR| 10 min to Navy Base
Enjoy historic charm with modern comfort in this fully renovated downstairs unit—no stairs to enter. This 1-bed, 1-bath home blends original character with updated finishes, kitchen, and bath. Perfect for work or relaxation and just a 10-minute drive to the Navy base. What you’ll love: ✅ Downstairs, step-free entry ✅ 1 bedrooms / 1 bath ✅ Fully renovated historic home ✅ Modern kitchen & bath ✅ 10 minutes to Navy base

Modern Navy Grad Stay | 3BR 2BA
🏡 Modern 3BR/2BA • 10 Minutes from Naval Base • Perfect for Navy Graduations! Welcome to your home away from home — a clean, comfortable 3BR retreat just 10 minutes from Naval Station Great Lakes. Designed for Navy families, long-weekend trips, and business travelers, this home offers a fenced backyard, full kitchen, fast Wi-Fi, private driveway, and a quiet residential neighborhood.

Modern Comfort 2King Beds, 2Full Bath by Navy Base
This fully updated 2-bedroom, 2-bath apartment combines modern comfort with tall ceilings and a bright, open feel. Both spacious bedrooms feature king-size beds, and one includes an attached full bath for added privacy. With sleek finishes throughout, this home is perfect for stylish, comfortable living. Near downtown Waukegan, 1 mile from Metra, 5 miles from Great Lakes Navy Station.

Modern home. Near naval base, Six flags and Casino
Quiet neighborhood in wauekgan, IL. Minutes away from Gurnee mills, Six Flags, and Naval Base, Waukegan beach and CASINO 50 minutes to downtown Chicago and 50 minutes to downtown Milwaukee Has everything you need. 600Mbps wifi. laundry on site. patio with lights. Fully finished Basement with entertainment kitchen is fully functional and has everything you need.
Popular amenities for Waukegan holiday rentals
Other great holiday rentals in Waukegan

Casa Monarca • 3.5 Bathrooms • Top 1%

Pet-friendly Property Near Asylum Skate Park!

Luxury 4BR near Six Flags & Naval Base

Stylish 4-Bed Home | Near Navy Base

Little House by the BIG LAKE

Historical Hideaway near Naval Base

Kalo House | Mid-Century Modern Retreat with Pool

Luxury 1 Bed/1 Bath Apartment | Downtown Waukegan
When is the best time to visit Waukegan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $212 SGD | $208 SGD | $209 SGD | $205 SGD | $209 SGD | $221 SGD | $239 SGD | $231 SGD | $231 SGD | $230 SGD | $231 SGD | $215 SGD |
| Avg. temp | -4°C | -2°C | 4°C | 10°C | 16°C | 21°C | 24°C | 23°C | 19°C | 12°C | 5°C | -1°C |
Frequently Asked Questions
What are the best places to stay in Waukegan?
Downtown Waukegan is often chosen for proximity to theaters, dining, and the lakefront, while residential neighborhoods can provide a quieter atmosphere. Areas near the harbor are convenient for outdoor activities and festivals.
What are the best things to do in Waukegan with kids?
Families can explore Waukegan Beach, play in Bowen Park, or discover hands-on exhibits at local museums. Community events and library programs also create engaging experiences for children of different ages.
What are some of the best things to do in Waukegan?
Explore the Genesee Theatre's lineup, stroll Waukegan Beach for lake views, or discover local art spaces in the downtown district. Visitors often enjoy seasonal festivals and outdoor recreation at the marina.
How is the weather in Waukegan?
Waukegan experiences cold winters with snow, around 19–37°F (-7–3°C), and warm, humid summers near 66–85°F (19–29°C). Spring and autumn are milder, but layers and rain protection are helpful due to variable conditions.
When is the best time to visit Waukegan?
Late spring through early autumn is often recommended, with pleasant temperatures around 60–80°F (16–27°C), blooming parks, and lively outdoor events. Those interested in lake activities or festivals may find this period especially enjoyable.
What are the best places to visit in Waukegan?
Many visitors explore the Genesee Theatre for performances, Waukegan Harbor for lakeside activities, and the Waukegan History Museum to learn about the city’s past. The local arts district also has galleries and murals to discover.
What are some hiking trails in Waukegan?
Waukegan has urban green spaces like Bowen Park with woodland paths and nature trails. The Waukegan Savanna Forest Preserve features walking routes through native prairie and wetlands.
What are some family activities we can do in Waukegan?
Enjoy lakeside picnics at Waukegan Beach, explore play areas in Bowen Park, or attend seasonal community festivals. Many families also visit local museums or take part in arts workshops around downtown.
What are some of the best day trip ideas from Waukegan?
Around Waukegan, explore nature preserves, stroll through nearby botanical gardens, or visit local wineries and farm stands. Prairies, lakeside towns, and vibrant arts communities add variety to day adventures.
Are there any pet friendly accommodations available in Waukegan?
Waukegan has a range of pet-friendly stays, especially around the lakefront and downtown. Many rentals allow pets, making it easier to enjoy nearby parks and walking trails together.
What are some local tips for visiting Waukegan?
Exploring the lakefront and arts district can give a sense of Waukegan's creative spirit. Locals often suggest trying neighborhood restaurants, checking calendars for live theater, and dressing in layers due to changing Lake Michigan breezes.
What is Waukegan known for?
Waukegan is known for its historic downtown, ties to author Ray Bradbury, and a lively performing arts scene anchored by the Genesee Theatre. The lakefront, public murals, and community festivals reflect the city’s cultural diversity.
What are the best hidden gems to explore in Waukegan?
Consider wandering through Waukegan's public murals, tucked-away coffee shops, or the little-known Bowen Park gardens. Locals sometimes suggest the Jack Benny Center for the Arts for community performances and classes.
What are the best foods to try in Waukegan?
Waukegan's culinary scene has Latin American flavors, classic Midwestern fare, and popular local bakeries. People often suggest trying handmade tamales, neighborhood barbecue, and house-made pastries alongside coffee.
What should I bring for a trip to Waukegan?
Pack for changing weather—layers, a light jacket, and comfortable walking shoes are helpful. If visiting the lake or parks, bring sun protection, a reusable water bottle, and a camera for the local art and scenery.
What is the nightlife in Waukegan like?
Waukegan has locally owned bars, live music venues, and performing arts spaces that create a relaxed evening atmosphere. Around downtown, you can explore casual spots, enjoy comedy shows, or sample food and drink with friends.
What are the most popular events or festivals in Waukegan?
Waukegan hosts a Parade of Lights during the winter holidays, bringing the community together for festive displays. Around the arts district and downtown, seasonal celebrations often highlight local music, food, and creative traditions. Many residents look forward to community gatherings and cultural festivals throughout the year.
Are there family friendly vacation rentals in Waukegan?
Many vacation rentals in Waukegan are family friendly, providing space and amenities for children and adults. Listings throughout downtown, the lakefront, and quieter residential areas are frequently suggested for visiting families.
Quick stats about holiday rentals in Waukegan

Total holiday rentals
Explore 270 holiday rentals in Waukegan

Nightly prices starting at
Waukegan holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 9,880 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 120 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wifi availability
270 of Waukegan holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Waukegan rentals

4.7 Average rating
Waukegan stays receive an average rating of 4.7 out of 5 from guests
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- Wrigley Field
- Lincoln Park
- United Center
- Soldier Field
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- Shedd Aquarium
- The Field Museum
- Humboldt Park
- Chicago River Walk
- Alpine Valley Resort
- University of Chicago
- SeatGeek Stadium
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Donald E Stephens Convention Center
- Union Park
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort





