Pet-friendly holiday rentals in Waukegan

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!

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

The Adorable "Blue Breeze"!

Enjoy time at our centrally-located, family-friendly home. Close by, you'll find a public fishing dock and the popular Phil's Beach. A peaceful space with an outside patio and grill, perfect for relaxing at end of day. We also have a large driveway that can accommodate your boat making it easy to enjoy a day on Bangs Lake or a short 15 min trip to Fox Lake. Nearby attractions include the Volo Museum, Jurassic Gardens, and Lake County Discovery Museum. Please note the backyard is not fenced in.

*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.

Modern French Escape | Near Base

Welcome to Your Chic French-Inspired Escape! Step into a stylish 4-bed, 2.5-bath retreat blending modern comfort with a touch of France. Just 2 miles from Six Flags, 4 miles from The American Place Casino, and 9 miles from the beach and Naval Station, this home is perfect for families and groups. Enjoy French-inspired décor, office nooks, a pool table, and board games for fun nights. The stocked kitchen makes meals easy. Near highways, shopping, and dining, this elegant getaway has it all!

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 !

Chic Oasis/Game Room/Near Base

Welcome to your perfect getaway! This spacious 5-bed, 2-bath ranch house offers a cozy stay just 4 miles from Great America, The American Place Casino, and the beach, and 6 miles from the Great Lakes Naval Station. Ideal for families or groups. Enjoy a fully fenced yard for outdoor fun or pets. Inside, relax in the welcoming living area with plenty of space, plus a fully equipped kitchen for all your cooking needs. This home has everything you need for a memorable stay!

Relax & Play! 9 Minutes from Naval Base Station

✨ Charming 3-Bedroom Home Near Naval Base | Sleeps 8 Welcome to your perfect family getaway! Ideal for families or groups visiting the nearby Naval Base, located just 9 minutes away. Enjoy a dedicated game room with several fun activities, while the living room features a Nintendo Switch for relaxing game nights. With plenty of space to unwind, play, and create lasting memories, this home offers comfort and entertainment for everyone. 🐾 Pets welcome for $25/day.

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.

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. One night stays are available on a limited basis - reach out for details!

A Wonderful Getaway Home on the North Shore!

A perfect place to visit the northern highlights of Chicago! 1/4 mile from Ravinia! 1.5 miles from the Botanic Gardens! 30 minutes from Chicago (an hour and a half from Milwaukee). Close to trains, planes, and easy automobile access. A two-bedroom gem in the heart of so many wonderful things. Other local places include Northwestern University, Lake Forest, Winnetka, and Lake County. I have a cat living here, but he will accompany me when I leave.

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.