Pet-friendly vacation rentals in North Chicago

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.

Lovely studio near the beach! (and heated floors!)

Get away from the city to this studio in Highland Park. The newly renovated space has everything you need for a relaxing getaway—huge comfy couch, brand new bed with Brooklinen + Parachute bedding, pristine bathroom, and lots of amenities. Downtown Highland Park, Highwood, + the beach are just a walk away. There's access to grocery stores, restaurants, and shops, and you can retreat to the quiet of your studio when you're ready to unwind. Ps. For the winter months: We've got heated floors.

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.

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 !

Your relaxing stay in Highland Park

Whether you are looking to escape the city hustle and bustle, visiting Lake Forest College, the Naval Station or moving cross country, our bright and spacious suite is the perfect spot to check in and relax for a few nights. Featuring a separate entrance and a beautiful, private newly remodeled bathroom. 43 4K Smart HDTV with Netflix and Prime and super fast WiFi available for streaming. Kitchenette with a microwave, mini fridge, sink and cups/plates/010/053/2026cutlery.

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.

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.

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!

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.