
House holiday rentals in Waukegan
Find and book unique houses on Airbnb
Top-rated house rentals in Waukegan
Guests agree: these houses are highly rated for location, cleanliness and more.

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.

Comfy, 1 Bedroom Apt. w/ Kitchen & Parking for 4
Enjoy our historic district three-flat w/ free parking in upscale, safe Oak Park just 3 blocks to the train, easy access to Chicago. Enjoy some tranquil time in our little eco suburban farm. Check out the gardens and visit our 6 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Spacious 2-br, 1 bath home w/AC near Naval Base
Welcome to our Airbnb, perfectly situated for your convenience. Located near the navy base, Six Flags Great America, and an hour drive to the bustling city of Chicago, our accommodations offer the ideal gateway to a multitude of attractions and activities. And when it’s time to rest, our comfortable accommodations awaits you. Whether you’re here for business or pleasure. At our Airbnb, we prioritize your comfort and convenience. Book now and let us be your gateway to an extraordinary stay.

Center Lake View Cottage, near Camp&Silver Lakes
Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch boat in Center Lake at end of street or several nearby lakes. Camp Lake is 2 mins away, close to Silver Lake and many others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Lake Geneva, & Renaissance Faire. Ski at Alpine Valley or Wilmot Mountain. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base.

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!

Retro Modern Bungalow | free parking | fire pit
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

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.

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!

Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

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.

Great Lakes Naval Station-Waukegan- Gurnee-6 Flags
Under 10 minutes to RTC Great Lakes (Graduations) Under 10 minutes Rosalind Franklin University 15 minutes to Six Flags Affordable, private and comfortable... These are just a couple reasons why this is the ideal room for you to settle into during your stay in the area! Whether it be for boot camp graduation, the medical schools in the area or maybe you’re just passing through; book your stay while its still available!

6th Ave Harborside
Perfectly located near downtown Kenosha, this cozy and comfortable home makes it easy to enjoy the best of the area. Ride the bikes to the farmers market, stroll to the beach, or spend time along the marina and harbor. The large dining room invites long meals and relaxed evenings together. An ideal home base for a peaceful getaway, visiting family, or attending local events. Reach out for seasonal specials!
Popular amenities for house rentals in Waukegan
House rentals with a pool

Elegant Executive Residence, Hot Tub & Pool

NEW! 3 Bedrooms, Grill, 70 inch TV, *KING Bed*!

#EnglishPrairieBnB | 4 Bedrooms | 2.5 Baths

Friends-Inspired Vintage Vibes House near Chicago

Family Getaway near Lake Geneva Winterfest

Paradise with Pool & Games

In Ground Pool, Full Ranch Home

Elmhurst 4BR Home with Pool | Mid-Term Ready
Weekly house rentals

Lakeside Getaway 1 Bedroom

Breezy Vista by Naval Base

Lakefront Modern 4BR w/ Dining & Beach

Lighthouse Retreat

Waterfront - Fox Lake - Bring your boat. 3bd 2bath

Green Magnolia House

Adorable 2-bedroom home near downtown Grayslake!

This one feels like Home
Private house rentals

Comfortable Home Stay | 4BD 1BA - 5 Queen Beds

J&J Vacay 2 story

Casa Monarca • 3.5 Bathrooms • Top 1%

Beautiful Twin Lakes home 2 mi from Wilmot Resort

Lake House Walk to Train-Chicago

Family~Friendly 3 BR/2 BA 5 bds Home near NavyBase

Suburban Serenity~Grill, Fire pit, Big yard~

Cozy Home near airport O’Hare
When is the best time to visit Waukegan?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $226 SGD | $238 SGD | $226 SGD | $257 SGD | $269 SGD | $274 SGD | $302 SGD | $272 SGD | $278 SGD | $263 SGD | $254 SGD | $236 SGD |
| Avg. temp | -4°C | -2°C | 4°C | 10°C | 16°C | 21°C | 24°C | 23°C | 19°C | 12°C | 5°C | -1°C |
Quick stats about house rentals in Waukegan

Total holiday rentals
Explore 140 holiday rentals in Waukegan

Nightly prices starting at
Waukegan holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 4,880 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wifi availability
130 of Waukegan holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Waukegan rentals

4.8 Average rating
Waukegan stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Chicago Holiday rentals
- Upper Peninsula Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Detroit Holiday rentals
- St. Louis Holiday rentals
- Cincinnati Holiday rentals
- Wisconsin River Holiday rentals
- Milwaukee Holiday rentals
- Windsor Holiday rentals
- Ann Arbor Holiday rentals
- Rentals with pools Waukegan
- Rentals with breakfast Waukegan
- Rentals with a fireplace Waukegan
- Family-friendly rentals Waukegan
- Pet-friendly rentals Waukegan
- Rentals with a washing machine and dryer Waukegan
- Rentals with outdoor seating Waukegan
- Rentals with a patio Waukegan
- Rentals with lake access Waukegan
- Hotel rooms Waukegan
- Rentals with a firepit Waukegan
- Fitness-friendly rentals Waukegan
- Flat rentals Waukegan
- House rentals Lake County
- House rentals Illinois
- House rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Soldier Field
- Alpine Valley Resort
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wilmot Mountain Ski Resort
- Wicker Park
- Lincoln Park Zoo
- Oak Street Beach
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower




