
Holiday houses in Waukegan
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Top-rated holiday rentals in Waukegan
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B’s Farmhouse Cottage 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, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

Nonsmoke, No Cleaning Fees, No Long Chore Lists.
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.

Cute & Cozy, 1bd Condo Apartment/townhouse
Enjoy a stylish experience at this centrally-located place. Unique split-level 1-bedroom condo with modern upgrades, stainless steel appliances, LED lighting, but extremely comfortable amenities. Located minutes from Walmart, restaurants, the Cancer Treatment Center. Reasonable driving distance from Great Lakes Naval Base, Six Flags, Gurnee Mills Shopping Center, Casino, Milwaukee & Chicago. Sleeps 3 (queen bed with mood setting lights + sleeper sofa). May not be ideal if stairs are an issue

Tiny home in not so tiny Yard
The house has a Queen bed, a Single bed and a sofa. A tiny home in a peaceful neighborhood. Built on 4 city lots, it has plenty of space and privacy. For families visiting the Naval Academy, we are close enough, yet give you space and privacy. Away from the hustle of North Chicago and Waukegan. Nearby attractions are: Naval Base - 11 miles, 20 minutes Six Flags - 7 miles, 15 minutes Illinois State Beach - 2 miles, 5 minutes Chicago - 46 miles, 60 minutes Milwaukee - 50 miles, 55 minutes

The Indigo Cottage
This is a newly remodeled single-family home! It is small but has everything you need to enjoy time with family and friends during your stay in the Chicagoland area! There are two bedrooms each with a queen bed, an updated bathroom, a dining room with seating for 6, a cozy living room with a Crate & Barrel pull-out queen sofa bed, and a nice, updated kitchen! There's a brand-new washing machine and dryer in the basement. There's a nice patio table outside too in the private yard. Welcome!

131 E. Park Ave - Unit 306
Keep it simple at this peaceful apartment walking distance to fantastic downtown Libertyville. Very nicely maintained building with elevator. 7 miles to Great Lakes Naval Base. Super clean unit with all brand new furnishings. HD smart TV's with cable in both the living room and bedroom. There is a comfortable rollaway bed behind the couch that is perfect for one person. Fast Wi-Fi with dedicated work desk. Ample free parking right in front of the building. On-site laundry one floor down.

The Victory Park Ranch - West
We are excited to welcome you to this comfortable and newly renovated modern house, in the perfect location if you're visiting Northern Illinois/Chicago. Come see why Waukegan is nicknamed "Green Town" and is home to some of the finest parks, ravines, and walking trails. With an incredible sandy beach, lakefront, galleries, breweries, restaurants, and more, it is definitely a place to check out! We are very close to Six Flags, Great Lakes Naval Base, and The Genesee Theatre too!

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!

Relax & Play! 9 Minutes from Naval Base Station
✨ Charming 3-Bedroom Home Near Naval Base | Sleeps 8 Welcome to your perfect family getaway! Ideal for families or groups visiting the nearby Naval Base, located just 9 minutes away. Enjoy a dedicated game room with several fun activities, while the living room features a Nintendo Switch for relaxing game nights. With plenty of space to unwind, play, and create lasting memories, this home offers comfort and entertainment for everyone. 🐾 Pets welcome for $25/day.

Your best choice* Cozy, spacious, comfortable, lg
Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

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!

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.
Popular amenities for Waukegan holiday rentals
Other great holiday rentals in Waukegan

Private Room in Large Home with Gym

Immense 2 Bedroom 1 Airbed - Apartment

T - Amazing Open Floor Plan, Across From Lake

Cozy, Peaceful, and Beautiful Private Room

Room within a Cozy Cottage

UltraPlush Queen Bed - 2nd Fl. Townhome Near Woods

Large PRIVATE Master Suite with Jacuzzi tub

"Magnolia Farmhouse" inspired 4-bedroom home
When is the best time to visit Waukegan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $248 NZD | $256 NZD | $233 NZD | $266 NZD | $271 NZD | $286 NZD | $309 NZD | $299 NZD | $299 NZD | $298 NZD | $299 NZD | $279 NZD |
| 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 $67 NZD per night before taxes and fees

Verified guest reviews
Over 9,520 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 130 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wi-Fi availability
260 of Waukegan holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Alpine Valley Resort
- Shedd Aquarium
- Soldier Field
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- Wilmot Mountain Ski Resort
- Oak Street Beach
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower




