Pet-friendly holiday rentals in Waukegan

4.94 out of 5 average rating, 180 reviews

A cozy living room features a pair of light-colored sofas and an accent chair, positioned around a rustic coffee table. A patterned area rug lies underfoot, while a mirror with a wooden frame and wall art enhance the space. A partial view of the kitchenette is visible in the background.

Home in Highland Park

Cozy 2-Bedroom Cottage Near Downtown Highland Park

Step into a warm, inviting retreat where comfort meets character! This beautifully updated suite features two cozy bedrooms, a private bathroom, and thoughtfully decorated living spaces in a modern farmhouse style. Nestled in the heart of Highland Park, you’re steps from great restaurants, boutique shops, scenic trails, and parks, plus a golf course across the street and just 1.5 miles from Lake Michigan. Whether it’s a family getaway or a business trip, it’s your perfect home away from home!

5 out of 5 average rating, 24 reviews

Home in North Chicago

Modern 4 BR 3 miles from Great Lakes Naval Base

Welcome to this modern Getaway next to Base! Make yourself at home in this modern 4BR, 1.5BA -Perfectly located 4 miles from Great Lakes Naval Base. Relax in the bright, open living room with smart TVs, fast Wi-Fi, and plenty of seating for family time. Prepare meals together in a fully stock kitchen, laundry, and private fenced yard with fire pit and BBQ. Designed for Navy Families, and leisure travelers, Enjoy cozy nights by the indoor fireplace and starry evenings around the outdoor fire pit

4.91 out of 5 average rating, 254 reviews

Guest suite in Zion

Cozy Mother inlaw Suite. Private. Next to beach.

30 minutes away from the Navy Base(Graduates). 5 minutes away from the newly renovated 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. This Mother in Law suite has tons of natural light. Private access and no shared indoor space. Safe and quiet neighborhood with plenty of wildlife right in the back yard. For nature lover’s this unit is close to the beach and there are walking trails nearby.

4.97 out of 5 average rating, 36 reviews

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

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

4.94 out of 5 average rating, 108 reviews

A welcoming living area features a plush, light-colored sectional sofa and an elegant coffee table. Soft lighting emanates from a chandelier, enhancing the warm tones of the walls. A decorative console table displays plants and a mirror, while a cozy blanket is draped nearby.

Home in Waukegan

*Entire house w/4 LG Bedrms, NAVY 4 miles/baseLake

We are excited to welcome you to this clean and spacious home/perfect location.10 mins /4 miles from Great Lakes. SLEEPS 5- 12!! A"Gathering Place" is for FAMILIES! Stay all together in one place and make memories! Waukegan has parks/cool pl! A Dock/ lakefront, galleries, breweries, restaurants, and more! Near the train station, if you want to travel to Chicago N Suburbs. Close to Six Flags, the Genesee Theatre and the new CASINO! The train is 2 blocks/travels to both Chicago and Wisconsin.

4.97 out of 5 average rating, 119 reviews

A charming sidewalk scene features a row of quaint storefronts with colorful awnings and flower boxes. Benches are placed alongside trees, and a brick pathway leads past a trash receptacle. The inviting atmosphere reflects a friendly downtown setting.

Home in Grayslake

Adorable 2-bedroom home near downtown Grayslake!

Welcome to Mellow Yellow, an adorable home with everything you need. Located close to downtown Grayslake where you will find restaurants, bars and cute hometown stores. Walk to Jones Island to relax on the beach or head to the Aquatic Family Center for a dip in the pool. Enjoy nearby attractions, Lake County Fairgrounds, Six Flags Great America, Great Lakes Naval Base, and Gurnee Mills Mall, or spend the day in Chicago which is 29 miles. Check out my guidebook for places to eat and visit!

4.81 out of 5 average rating, 1,029 reviews

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Flat in Downtown Chicago

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

4.96 out of 5 average rating, 238 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 !

4.9 out of 5 average rating, 130 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 cozy and comfortable Airbnb, perfectly located near Naval Station Great Lakes (approximately 5-7 min., 2 miles), Six Flags Great America, and just an hour from downtown Chicago! Whether you're visiting for Navy graduation, family time, business, or a weekend getaway, our home offers the perfect balance of convenience and relaxation. We take pride in providing excellent hospitality and a smooth, stress-free experience from check in to check out.

4.95 out of 5 average rating, 136 reviews

A spacious living area features modern furniture, including a leather sofa and armchairs arranged around a coffee table. A dining table with blue chairs is visible, complemented by large windows allowing natural light. The room has a warm and neutral color palette.

Loft in Libertyville

Historic Downtown Libertyville Loft

Enjoy a stylish experience at this centrally-located 1600 square foot place. Located in the heart of Downtown Libertyville, half way between Chicago and Milwaukee. Close to Six Flags, Great Lakes Navy Base, Lake Michigan beaches, forest preserves, train station and the Chain of Lakes. Downtown Libertyville is a trendy town offering several restaurants, shops and fun events. Book one of the only units truly Downtown Libertyville.

4.84 out of 5 average rating, 102 reviews

The exterior of a single-story home is showcased with a spacious deck leading to a grassy yard. A large tree provides shade nearby, and the facade features clean white siding with several windows reflecting natural light.

Home in Round Lake Beach

Lake/Beach Getaway (Remodeled)

Have fun with the whole family at this stylish home. Everything has been recently renovated. This is directly across from a beach, which is perfect for winter and summer activities. We supply 2 kayaks, fishing poles (Bring your fishing boat)This place has 3 bedrooms, and a total of 5 beds. There is also a lot of dining and shopping, nearby. This is a hidden gem and brand new to AirBnb.