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
4.9 out of 5 average rating, 231 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 favourite
Flat 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 favourite
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
4.95 out of 5 average rating, 19 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 favourite
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.

Superhost
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
4.85 out of 5 average rating, 26 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
4.93 out of 5 average rating, 147 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
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, 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 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, 23 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
Home in Waukegan
4.9 out of 5 average rating, 48 reviews

Spacious 5 Beds 2 baths RTC Navy Casino

Centrally located, perfect for families attending Navy graduations, weddings, family reunion, or simply a get-away. Side by side twin home (duplex) has no adjacent walls. A garage divides the two houses and is use for storage. It is complete with dishwasher, Keurig, fresh towels, linen, soap, and other essential. Relax and spend quality with the whole family in comfort. Southern facing home, which means lots of sun. House is located on corner lot with many over size windows!

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, 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!

Guest favourite
Home in Waukegan
5 out of 5 average rating, 8 reviews

Remodeled Waukegan Oasis | 4 Bed 2 Bath House NEW

We are excited to welcome you to this charming and spacious apartment if you're visiting Waukegan/Chicagoland. We are very close to Great Lakes Naval Station, Six Flags and Lake Michigan. Working, relaxing, living. Our space has all the other essentials you need for your stay. - Contact-free check-in - 24/7 virtual support - Xfinity Wi-Fi - Fresh towels and bathroom essentials - Pre-cleaning before your arrival - Fully equipped kitchen - NETFLIX and HDMI for streaming

Guest favourite
A modern living area is captured, featuring a large sectional sofa arranged around a circular coffee table. A textured area rug covers the floor, and natural light fills the space from the multiple windows. A ceiling fan and a wall-mounted television add functionality, while decorative elements enhance the cozy ambiance.
Flat in Grayslake
4.95 out of 5 average rating, 75 reviews

Apartment in Downtown Grayslake

Welcome to downtown Grayslake! Enjoy your stay in our quaint one-bedroom apartment overlooking Center Street. Nestled above our lifestyle boutique, 27 Houses, you can enjoy everything our adorable town has to offer. Grayslake is practically straight out of a Hallmark movie, and you'll be right in the center of everything. With a cozy floorpan, enjoy a cup of coffee, listen to some vinyl, or get right to work at our dedicated workspace. We're excited to welcome you!

Popular amenities for Waukegan holiday rentals

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Quick stats about holiday rentals in Waukegan

  • Total holiday rentals

    Explore 240 holiday rentals in Waukegan

  • Nightly prices starting at

    Waukegan holiday rentals start at € 35 per night before taxes and fees

  • Verified guest reviews

    Over 8,760 verified reviews to help you choose

  • Family-friendly holiday rentals

    170 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 120 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wifi availability

    230 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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