Holiday rentals in Waukegan

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Top-rated holiday rentals in Waukegan

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Guest suite in Zion
4.91 out of 5 average rating, 240 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.

Guest favourite
A spacious living area features a blue couch facing a large television mounted on the wall. A decorative rug complements a wooden dining table set for four, accented with plates and glassware. Natural light filters through large windows, enhancing the inviting layout.
Home in North Chicago
4.88 out of 5 average rating, 107 reviews

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.

Guest favourite
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, 133 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 favourite
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, 156 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!

Guest favourite
A spacious living area is furnished with a dark sofa and light gray armchair. A round coffee table sits centrally, while a mounted flat-screen TV is positioned on the wall. Natural light filters in through a large window, enhancing the serene atmosphere.
Flat in Libertyville
4.82 out of 5 average rating, 103 reviews

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.

Top guest favourite
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.
Flat in Beach Park
4.97 out of 5 average rating, 438 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 favourite
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, 28 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.

Guest favourite
A spacious kitchen is equipped with wooden cabinets and modern appliances, including a refrigerator and stove. A central island with seating for three is visible, alongside a dining table. Natural light enters through multiple windows, enhancing the warm tones of the room.
Home in Libertyville
5 out of 5 average rating, 20 reviews

Home w/ porch in DT Libertyville Near Naval Base

Charming 3 bedroom, 1.5 bath home. Five minute walk to downtown Libertyville which has many different shows and restaurants for people of all ages to explore. Close to everything. Home features One King Bed, 2 Queen Beds, and a full size pull out couch and 2 single rollaway beds. Home sleeps 10 comfortably. -Fully Equipped Kitchen -Free Unlimited High Speed Internet -Keurig Coffee Maker w/ K Cups -Crock Pot Slow Cooker -ROKU TVs -Parking for up to 4 Cars -Central AC -Washer & Dryer

Guest favourite
Home in Waukegan
4.86 out of 5 average rating, 152 reviews

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.

Top guest favourite
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, 184 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!

Guest favourite
A modern living room is presented with a large window allowing natural light to fill the space. A comfortable sofa, adorned with colorful pillows, faces a wooden coffee table, while a dining area with wooden chairs is visible in the background.
Loft in Waukegan
4.95 out of 5 average rating, 201 reviews

The Office Loft

We are very excited to welcome you to this comfortable and high-quality, modern apartment, in the perfect location if you're visiting Northern Illinois. 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 a place to check out! We are very close to Six Flags, Great Lakes Naval Base, and The Genesee Theatre too!

Top guest favourite
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.
Flat in Winthrop Harbor
4.94 out of 5 average rating, 323 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.

Popular amenities for Waukegan holiday 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 holiday rentals in Waukegan

  • Total holiday rentals

    Explore 270 holiday rentals in Waukegan

  • Nightly prices starting at

    Waukegan holiday rentals start at € 34 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    260 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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