House vacation rentals in Waukegan

4.98 out of 5 average rating, 161 reviews

The living area features a cozy sofa and a patterned armchair, complemented by a glass coffee table. A television is positioned in one corner. Large windows invite natural light, while floor-to-ceiling curtains offer privacy. A potted plant adds a touch of greenery.

Home in Wilmette

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Superhost

The kitchen is designed with modern cabinetry in muted green, featuring a stainless steel refrigerator and stove. A dining table with wooden chairs is present, alongside a neutral area rug. Bright, overhead lighting illuminates the space, creating a functional cooking and dining environment.

Home in Beach Park

4.79 out of 5 average rating, 66 reviews

Cozy 2 bedroom home with a study

This newly remodeled chicken coop turned into a 2 bedroom A frame home is 50 miles from Milwaukee, 47 miles from Chicago, and 10 miles from the Naval Station. We are a couple minutes away from City of Hope, Six Flags Great America, Bristol Renaissance Faire, Great Wolf Lodge, American Place Casino, and the beach. There is also a Target and Starbucks down the road, what more can you ask for! The stairs to the bedrooms are steep and narrow so please be careful. Please enjoy the home to yourselves

4.96 out of 5 average rating, 131 reviews

The cozy living room is designed with soft seating arrangements and a wooden coffee table at the center. Natural light flows through nearby windows, enhancing the inviting atmosphere. A chandelier and wall mirror add character, while decorative accents on the table provide visual interest.

Home in Highland Park

Charming Ranch-Style Cottage

Escape the hustle and bustle of the city in this relaxing, cozy, cottage that is a few blocks away from downtown Highland Park and Highwood, with great restaurants, bars and coffee shops. It is perfect for single travelers, couples, or a small family. We are grateful for the amazing Airbnb hosts across the globe, who opened their homes to us, and made our trips so memorable. So when we bought our own home, it was only right that we would return the favor and open our home to fellow adventurers

4.98 out of 5 average rating, 228 reviews

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

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.

4.9 out of 5 average rating, 87 reviews

A spacious living area features a blue couch facing a large television mounted on the wall. A decorative rug complements a wooden dining table set for four, accented with plates and glassware. Natural light filters through large windows, enhancing the inviting layout.

Home in North Chicago

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.

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.

4.92 out of 5 average rating, 131 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!

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.

4.92 out of 5 average rating, 13 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.

4.95 out of 5 average rating, 193 reviews

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Superhost

A cozy living area features a blue sofa, a yellow couch, and a patterned rug underfoot. A wooden accent wall connects to the kitchen, enhancing the open layout. Natural light enters through dark-curtained windows, and decorative artwork adds visual interest to the space.

4.86 out of 5 average rating, 135 reviews

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.

A modern living room features a large sectional sofa positioned next to a pair of armchairs. Three windows provide natural light, framed by soft curtains. A sleek side table sits beside the sofa, and hardwood flooring extends throughout the space.

4.97 out of 5 average rating, 156 reviews

The Brick Arch

We are excited to welcome you to this comfortable and newly renovated charming home 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!

Superhost

A charming two-story lake house is presented, featuring a prominent American flag and a large white flag. A spacious veranda overlooks the fenced yard, while bare trees frame the house against a bright blue sky with scattered clouds.

Home in Round Lake Beach

4.89 out of 5 average rating, 214 reviews

Corner Lakefront Property

This unique place has a style all its own. This corner lake house comes with a huge fenced-in yard, as well as a balcony off of the master bedroom and 2 parking spots. We offer 3 kayaks with life jackets, 1 paddle board, paddle boat and fishing poles, fire pit, outdoor and indoor games. We have 3 bedrooms with beds included, as well as a futon couch a trundle bed and a pull-out couch bed (6 potential beds total). This comes with 2 TVs, fireplace, WiFi, bar, new fridge and more.