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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Guest favourite

Home in Beach Park

4.98 out of 5 average rating, 161 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.

Apr. 24 – May 1

$214 CAD per night

Guest favourite

Guest suite in Riverwoods

4.95 out of 5 average rating, 304 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.

May 20 – 25

$242 CAD per night

Guest favourite

Home in Waukegan

4.91 out of 5 average rating, 65 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!

Jun. 24 – Jul. 1

$221 CAD per night

Guest favourite

Home in Round Lake Beach

4.99 out of 5 average rating, 102 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!

Dec. 8 – 13

$291 CAD per night

Guest favourite

Guest suite in Zion

4.89 out of 5 average rating, 142 reviews

Non-smoking, attached mother-in-law suite.

30 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour to O’Hare Airport and downtown Chicago. 1 hour to Milwaukee 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 7PM.

May 16 – 23

$117 CAD per night

Superhost

Apartment in Waukegan

4.9 out of 5 average rating, 70 reviews

Luxury 2 BDR Downtown Waukegan | Pool Table

We are excited to welcome you to this charming and spacious apartment if you're visiting Northern Illinois/Chicago. We are very close to Six Flags, Great Lakes Naval Base 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

Jun. 8 – 15

$252 CAD per night

Guest favourite

Home in Kenosha

4.97 out of 5 average rating, 197 reviews

Lovely home near the beach in a safe neighborhood

Our simple, yet welcoming property is minutes away from beaches, downtown, minor league baseball, the farmers market, and many delicious restaurants, as well as having close proximity to Carthage College, 6 Flags, and a quiet 30 min drive to Great Lakes Naval Base. We are located in the Allendale neighborhood boasting a family-friendly atmosphere on a quiet street. Whether you are here to relax, have fun, or attend special events, our house can provide.

Mar. 6 – 13

$213 CAD per night

Guest favourite

Apartment in Winthrop Harbor

4.94 out of 5 average rating, 228 reviews

Love my guests! Homey Elegant & Lake Michigan!

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.

Oct. 6 – 13

$112 CAD per night

Superhost

Apartment in Waukegan

4.8 out of 5 average rating, 5 reviews

Cozy Apartment | Naval Station

Surround yourself with style in this standout space. Our home includes full furnished kitchen, WiFi, and new flooring! BEDROOM / LIVING ROOM 1 Queen size bed 2 Sofa beds TV Shelf Space Dedicated workspace Fresh clean linens KITCHEN & DINING Microwave Oven Stove Refrigerator/Freezer Coffee Maker + Coffee essentials Sink Trays Glasses Silverware Pots BATHROOM Bath with a Shower Mirror Toilet Towels Essentials Toiletries

Aug. 16 – 23

$183 CAD per night

Guest favourite

Apartment in Kenosha

4.98 out of 5 average rating, 115 reviews

Downtown-Treetop Deck-2Bd/2Bth

This one-of-a-kind, shabby-chic second floor apartment is in the heart of Downtown Kenosha, walking distance to coffee shops, restaurants, museums, and Lake Michigan beaches. Enjoy the large, completely secluded back deck equipped to grill, dine, and relax tucked amongst neighborhood buildings with a tree top view. The apartment is great for a romantic rendezvous, a girlfriend getaway, or for an extended stay.

Nov. 3 – 10

$200 CAD per night

Guest favourite

Home in Lake Bluff

4.92 out of 5 average rating, 103 reviews

Home Sweet Home, minutes to Great Lakes Naval Base

Home Sweet Home is located 35 miles north of Chicago; 53 miles south of Milwaukee, WI; and just 4 miles east of Great Lakes Naval Base. Chicago is a 45-minute train ride away. O'Hare is a 30 to 40-minute commute. Great America amusement park and shopping venues, including Gurnee and Kenosha outlet malls, are all within 20 to 30 minutes away. Location makes this home an ideal respite for Midwest sightseeing.

Dec. 1 – 8

$235 CAD per night

Guest favourite

Cabin in Kenosha

4.81 out of 5 average rating, 539 reviews

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! Fully remodeled. Perfect for ice fishing in the winter. A Sportsman’s paradise. Ideal for the adventurous. Relax, do some writing or work overlooking the breathtaking scenery. A stone's throw to the beach. Massive deck overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

Oct. 21 – 28

$183 CAD per night