
Vacation rentals in Waukegan
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Top-rated vacation rentals in Waukegan
Guests agree: these stays are highly rated for location, cleanliness, and more.

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

Spacious 2-br, 1 bath home w/AC near Naval Base
Welcome to our Airbnb, perfectly situated for your convenience. Located near the navy base, Six Flags Great America, and an hour drive to the bustling city of Chicago, our accommodations offer the ideal gateway to a multitude of attractions and activities. And when it’s time to rest, our comfortable accommodations awaits you. Whether you’re here for business or pleasure. At our Airbnb, we prioritize your comfort and convenience. Book now and let us be your gateway to an extraordinary stay.

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.

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!

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.

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.

Minutes from naval base casino and six flags
Your family will be close to everything when you stay at this centrally-located place. Naval base and six Flags great America and NEW CASINO are just down the road less than 10 minutes . We are only about 45 min from downtown chicago. About 35 from O’Hare. And less than 10 from Gurnee mills. Plenty of restaurants within minutes and Starbucks is only 3 minutes away. 10 mins from Waukegan beach The house sits on 3 property lot, so it’s very private with no real next door neighbors.

Cozy mother inlaw suite. Private. Next to beach.
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.

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!

Luxury 4BR near Six Flags & Naval Base
Escape to a stunningly designed 4 bedroom modern home, where luxury meets convenience. Designed for making unforgettable memories, this spacious retreat offers the ideal blend of social spaces and private relaxation, all anchored by a chef's dream kitchen. - 4 Bedrooms - Full Kitchen - 2 Living rooms - 2 full bathrooms - In-unit Laundry room (Washer & Dryer) - Free Parking: 6 Vehicles Ideal for: - Navy Family - Tourist - Workshop - Family time

* Cozy Wauk-Townhse near navy base
Where you'll be This home is located near the intersection of Belvidere Rd & Powell Ave. in Waukegan. It is located in a peaceful neighborhood. There are a lot of activities nearby; Six Flags- Great America is 5 miles away, and the Grayslake Navy base is located 3 miles away. Lake Michigan is also located nearby. Boating/kayaking is available nearby during summertime. The city of Chicago and Milwaukee are located about an hour away.
Popular amenities for Waukegan vacation rentals
Other great vacation rentals in Waukegan

Timeless Charm Modern Space |10 Min to Navy Base

Cozy Apartment I Naval Station

Modern & Spacious Retreat • Fast Wi-Fi •Desk• Yard

The Serenity: Gurnee, Six Flags, Naval Base

Gurnee Gathering Place Near Navy Base

Beautiful home for Naval families!

Luxury 1 Bed/1 Bath Apartment | Downtown Waukegan

Cozy 3 BR Apartment split house in Waukegan.
When is the best time to visit Waukegan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $149 | $154 | $140 | $160 | $163 | $172 | $186 | $180 | $180 | $179 | $180 | $168 |
| Avg. temp | 25°F | 29°F | 39°F | 50°F | 61°F | 71°F | 75°F | 74°F | 66°F | 54°F | 41°F | 31°F |
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 vacation rentals in Waukegan

Total vacation rentals
Explore 270 vacation rentals in Waukegan

Nightly prices starting at
Waukegan vacation rentals start at $40 per night before taxes and fees

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

Family-friendly vacation rentals
190 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 130 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wi-Fi availability
260 of Waukegan vacation rentals include wi-fi 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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