Holiday rentals in Waukegan

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Top-rated holiday rentals in Waukegan

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Top guest favourite
A cozy living room features a large black sectional sofa adorned with patterned throw pillows. Bright natural light enters through multiple windows, framed by sheer white curtains. A decorative wall art piece and a console table with decorative items add to the inviting ambiance.
Flat in Waukegan
4.97 out of 5 average rating, 70 reviews

Apt Minutes from Naval Station

Welcome to our cozy 2-bedroom apartment, conveniently located just minutes away from Naval Station Great Lakes. Whether you're visiting for military duties or simply exploring the beautiful Great Lakes region, our comfortable and well-appointed apartment is your ideal stay. Additionally, easy access to nearby attractions, including: - Great Lakes Naval Museum - Six Flags Great America - Gurnee Mills Shopping Mall - Lake Michigan's beautiful beaches - Numerous dining options and local breweries

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, 250 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.

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
Flat in Kenosha
4.98 out of 5 average rating, 49 reviews

Blue Sky Landing

Enjoy a comfortable stay at this centrally-located studio.Walking distance to popular restaurants/ taverns, Downtown and Lake Michigan.Separate private entrance for all units. Kitchenette with microwave, airfryer and toaster plus fully stocked cabinets for everything you need to stay in and enjoy meals.Water cooler with hot/cold water and Keurig coffee maker with a selection of premium coffees and teas.Nice size bathroom with shower and jacuzzi bath. Salon quality Shampoo/Conditioner provided

Guest favourite
A comfortable living area is designed with a gray sofa and a black coffee table, complemented by a dining table. A work desk is positioned near large windows, allowing natural light. A ceiling fan is visible, and a flat-screen TV is mounted on the wall.
Flat in Libertyville
4.88 out of 5 average rating, 34 reviews

305

Kick back and relax in this calm, stylish space. This peaceful, quiet apartment is walking distance to beautiful downtown Libertyville. The building is very nicely maintained with an elevator. Located 7 miles from Great Lakes Naval Base and 35 miles from downtown Chicago. The unit is very clean with all brand new furnishings and appliances including HD tv's in both the living room and bedroom. Free ample parking. On-site laundry one floor down. Fast wifi with a dedicated work space.

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, 155 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 favourite
The living area features a spacious sectional sofa and a modern armchair positioned around a low coffee table. Large windows provide natural light and a view of the lush green outside. Wall art adds visual interest to the room, complemented by warm wooden flooring.
Home in Waukegan
4.94 out of 5 average rating, 106 reviews

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!

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, 181 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 Waukegan
5 out of 5 average rating, 11 reviews

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.

Guest favourite
Home in Waukegan
5 out of 5 average rating, 7 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 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.

Top guest favourite
An airy living area is highlighted by natural light filtering through large windows. A gray sofa with patterned cushions faces a round coffee table and is complemented by green accent chairs. A dining area is visible in the distance, featuring a wooden table and chairs.
Home in Kenosha
4.98 out of 5 average rating, 45 reviews

Lighthouse Retreat

Discover a unique lakeside-style retreat in the heart of Kenosha! Perfectly situated just minutes from three colleges, downtown attractions, and within walking distance of the stunning Lake Michigan shoreline. Whether you're here to explore or unwind, our home offers the ideal base to enjoy all that Kenosha has to offer!

Popular amenities for Waukegan holiday rentals

When is the best time to visit Waukegan?

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Avg. price$188 SGD$194 SGD$177 SGD$202 SGD$206 SGD$217 SGD$235 SGD$227 SGD$227 SGD$196 SGD$202 SGD$183 SGD
Avg. temp-4°C-2°C4°C10°C16°C21°C24°C23°C19°C12°C5°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 $50 SGD 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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