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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Top guest favorite
Guest suite in Zion
4.9 out of 5 average rating, 230 reviews

Nonsmoking, no cleaning fees, mother-in-law suite.

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 favorite
Apartment in Kenosha
4.98 out of 5 average rating, 42 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 favorite
A modern living area features a gray sectional sofa and a round coffee table centered on a patterned area rug. A staircase with a dark wooden railing is visible on the side. A large piece of artwork brightens the wall, complemented by a tall potted plant.
Townhouse in Zion
4.94 out of 5 average rating, 18 reviews

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

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, 432 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, 123 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
4.93 out of 5 average rating, 146 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 favorite
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.
Apartment in Libertyville
4.8 out of 5 average rating, 92 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 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, 429 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 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, 170 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, 15 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!

Guest favorite
A cozy living area features a black leather sofa paired with decorative pillows. A glass coffee table sits atop a patterned rug, complemented by a lamp and a small plant. The staircase leads to an upper level, with a wall map artwork enhancing the space.
Townhouse in Hoffman Estates
4.9 out of 5 average rating, 353 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Top guest favorite
The dining area features a glass table surrounded by mid-century chairs, illuminated by natural light from large windows. A comfortable sofa is positioned nearby, with greenery visible outside. Soft curtains frame the windows, enhancing the spacious feel of the open layout.
Home in Waukegan
4.93 out of 5 average rating, 76 reviews

The Oak Tree Ranch

This Mid-Century Modern Ranch home features a large White Oak Tree that gracefully shades this beautifully updated home! We are located just 13 minutes from the Great Lakes Naval Station and this is the perfect location to celebrate your loved one's graduation from Boot Camp, as well as enjoy all the wonderful places and sights in the Chicagoland area. You'll love the large floor-to-ceiling windows and all the unique MCM furniture in this lovely home.

Popular amenities for Waukegan vacation rentals

When is the best time to visit Waukegan?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,170 GYDG$32,216 GYDG$29,287 GYDG$33,471 GYDG$34,099 GYDG$35,981 GYDG$35,145 GYDG$36,400 GYDG$35,563 GYDG$33,471 GYDG$33,471 GYDG$30,333 GYD
Avg. temp-4°C-2°C4°C10°C16°C21°C24°C23°C19°C12°C5°C-1°C

Frequently Asked Questions

  • Are there pet-friendly hotel rentals in Waukegan?

    Four-legged friends are welcome in Waukegan. Choose from more than 10 hotel rentals for guests traveling with pets.

  • Do house rentals in Waukegan have free parking?

    Absolutely! We offer over 100 house rentals with free parking in Waukegan. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Waukegan have air conditioning?

    Absolutely! We offer over 10 villa rentals with air conditioning in Waukegan. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in townhouse rentals in Waukegan?

    Experience the best of Waukegan with our townhouse rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly apartment rentals in Waukegan?

    Waukegan has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Hotel Rentals in Waukegan?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Waukegan have wifi?

    Absolutely! We offer over 50 apartment rentals with wifi in Waukegan. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Waukegan have a kitchen?

    Absolutely! We offer over 10 hotel rentals with a kitchen in Waukegan. Enjoy a tailored experience with all the comforts you desire.

  • Are there Waukegan hotel rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 hotel rentals with pools in Waukegan, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there hotel rentals with a dedicated workspace in Waukegan?

    Yes! Work meets play with ease at over 10 hotel rentals in Waukegan featuring dedicated workspaces. Stay connected and productive in your home away from home.

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 G$8,368 GYD 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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