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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Superhost
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
4.94 out of 5 average rating, 103 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 favourite
A welcoming living area features a comfortable gray couch and a green decorative bench. Light wood flooring extends throughout, with a black coffee table at the center. Large sliding glass doors provide access to the outdoor space, allowing natural light to fill the room.
Home in Beach Park
4.98 out of 5 average rating, 263 reviews

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.

Superhost
Home in Waukegan
4.94 out of 5 average rating, 31 reviews

Naval Base 10 Min - Cozy Home

Newly Remodeled & Spacious Home Near Top Attractions! Welcome to your home away from home! This beautifully remodeled house offers plenty of space and comfort for your stay. With 4 bedrooms, 5 beds, and 1.5 baths, it comfortably accommodates up to 8 guests. Conveniently located just: ✅ 10 minutes from Great Lakes Naval Base ✅ 10 minutes from American Place Casino ✅ 15 minutes from Six Flags Great America & Gurnee Mills Perfect for anyone looking to enjoy everything the area has to offer!

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, 169 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
Home in Waukegan
4.86 out of 5 average rating, 156 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.

Guest favourite
Guest suite in Zion
4.91 out of 5 average rating, 248 reviews

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.

Top guest favourite
Home in Round Lake Beach
4.99 out of 5 average rating, 199 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 favourite
Home in North Chicago
4.89 out of 5 average rating, 119 reviews

Spacious 2-br, 1 bath home w/AC near Naval Base

Welcome to our cozy and comfortable Airbnb, perfectly located near Naval Station Great Lakes (approximately 5-7 min., 2 miles), Six Flags Great America, and just an hour from downtown Chicago! Whether you're visiting for Navy graduation, family time, business, or a weekend getaway, our home offers the perfect balance of convenience and relaxation. We take pride in providing excellent hospitality and a smooth, stress-free experience from check in to check out.

Top guest favourite
Flat in Beach Park
5 out of 5 average rating, 30 reviews

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.

Guest favourite
Home in Waukegan
5 out of 5 average rating, 18 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

Superhost
Flat in Waukegan
5 out of 5 average rating, 10 reviews

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.

Guest favourite
A spacious living area features a large sectional sofa arranged around a modern coffee table. A large flat-screen television displaying a serene sunset is mounted on the wall. Decorative plants and a mirror add subtle elegance to the room, which is well-lit with recessed lighting.
Home in Waukegan
4.89 out of 5 average rating, 53 reviews

Breezy Vista by Naval Base

We are excited to welcome you to this Charming and Centrally located House if you're visiting Northern illinois / Chicago. we are very close to Genesee theatre. Six flags, Great Lakes Naval Base and Michigan. Working, Living, Our space has all the other essentials you need for your stay- Contact-free Check-in

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 9,880 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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