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.

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Guest favorite
A welcoming living area features a plush, light-colored sectional sofa and an elegant coffee table. Soft lighting emanates from a chandelier, enhancing the warm tones of the walls. A decorative console table displays plants and a mirror, while a cozy blanket is draped nearby.
Home in Waukegan
4.98 out of 5 average rating, 92 reviews

*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!! The "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.

Top guest favorite
Guest suite in Zion
4.91 out of 5 average rating, 239 reviews

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.

Top guest favorite
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, 446 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.

Guest favorite
A spacious living area is furnished with a light-colored sofa, a coffee table, and a single bed draped in a patterned bedspread. Natural light filters through window blinds, illuminating the room. An air conditioning unit is positioned near the entrance, and a ceiling fan sits in the corner.
Tiny home in Beach Park
4.85 out of 5 average rating, 129 reviews

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

Top guest favorite
The modern kitchen features stainless steel appliances, including a refrigerator and stove. Light-colored cabinets provide ample storage, while a window allows natural light to brighten the space. A small table with chairs is positioned against the wall, enhancing functionality.
Home in Waukegan
4.94 out of 5 average rating, 154 reviews

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!

Top guest favorite
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, 437 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.

Top guest favorite
A historic home is showcased with a faded blue exterior and a prominent black star on the front. The entrance is framed by a white pergola, and a decorative gate leads to a garden adorned with red, white, and blue bunting, capturing an inviting atmosphere.
Home in Waukegan
4.96 out of 5 average rating, 26 reviews

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.

Top guest favorite
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, 179 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!

Top guest favorite
A vibrant studio features an orange bedspread on a spacious bed, complemented by a colorful mural in the background. A sleek kitchen with a bright green refrigerator and bar seating is visible. Natural light is provided by a window, while modern lighting fixtures enhance the decor.
Loft in Libertyville
5 out of 5 average rating, 22 reviews

The Hummingbird | Center of Downtown Libertyville

Welcome to The Hummingbird, a charming 375 sq ft studio in Historic Downtown Libertyville. Eclectic and stylish with Smeg appliances and high end finishes. Steps from top restaurants, nightlife, shops, and the Metra station. In the heart of the action, sharing a lively courtyard with one of Libertyville’s most popular restaurants. Perfect for couples or solo travelers who love being where the buzz is. Perfect for Navy Graduation or trips back to your home town!

Top guest favorite
Home in Waukegan
5 out of 5 average rating, 6 reviews

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

Top guest favorite
A spacious and comfortable living area is showcased, featuring a large sectional sofa with decorative pillows and a cozy throw. A coffee table, holding magazines and a candle, complements the soft brown carpet. The kitchenette area, equipped with a full-sized refrigerator, is visible in the background.
Apartment in Winthrop Harbor
4.94 out of 5 average rating, 321 reviews

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.

Guest favorite
A two-story house is viewed from the front, featuring a covered porch with railings on both levels. Surrounding trees provide shade, and a fenced yard is visible in the foreground. Outdoor furniture can be seen on the porch, suggesting a comfortable space for relaxation.
Home in Waukegan
4.88 out of 5 average rating, 117 reviews

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!

Popular amenities for Waukegan vacation rentals

When is the best time to visit Waukegan?

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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 240 vacation rentals in Waukegan

  • Nightly prices starting at

    Waukegan vacation rentals start at € 34 per night before taxes and fees

  • Verified guest reviews

    Over 8,760 verified reviews to help you choose

  • Family-friendly vacation rentals

    170 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    230 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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