Holiday rentals in Waukegan

The Brick Flat – Lower

Welcome to this charming flat in the heart of Waukegan, offering comfort, space, and a convenient location. Set in a classic brick home, the flat features bright living areas, cozy bedrooms, & a equipped kitchen ideal for short or extended stays. Enjoy nearby Bowen Park & Victory Park for walks and outdoor time. Waukegan Harbor & Lake Michigan are just minutes away. Naval Station Great Lakes is approximately 15 min. away, making this a great choice for military visits, work trips, or getaways.

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.

Nonsmoke, No Cleaning Fees, No Long Chore Lists.

25 minutes away from the Naval Station 5 minutes away from the 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 and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 8PM.

The Green Door - safe and calm with walkability

This charming guesthouse in Lake Forest is only steps away from beautiful Market Square — the historic retail center of the community. Inside it features loads of light, in-unit washer and dryer, a well-equipped kitchen and a professionally designed stylish and calming interior. Outside, it has a vintage (ie. older) porch/breezeway with classic outdoor games. Walk to two grocery stores, bars/restaurants and our historic train station that connects to Chicago and various corporate shuttles.

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!

131 E. Park Ave - Unit 306

Keep it simple at this peaceful apartment walking distance to fantastic downtown Libertyville. Very nicely maintained building with elevator. 7 miles to Great Lakes Naval Base. Super clean unit with all brand new furnishings. HD smart TV's with cable in both the living room and bedroom. There is a comfortable rollaway bed behind the couch that is perfect for one person. Fast Wi-Fi with dedicated work desk. Ample free parking right in front of the building. On-site laundry one floor down.

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!

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.

Your best choice* Cozy, spacious, comfortable, lg

Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

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.

Navy Graduation Stay | 3BR Near Great Lakes Base

🏡 Modern 3BR/2BA • 10 Minutes from Naval Base • Perfect for Navy Graduations! Welcome to your home away from home — a clean, comfortable 3BR retreat just 10 minutes from Naval Station Great Lakes. Designed for Navy families, long-weekend trips, and business travelers, this home offers a fenced backyard, full kitchen, fast Wi-Fi, private driveway, and a quiet residential neighborhood.

Hidden Gem Apartment

Renovated from floor to ceiling this private apartment is tucked on a quiet street near downtown Waukegan. Brand new everything, Netflix and chill on real leather! Details were not missed. Location is excellent. This unit is private but you won't feel secluded with lots of life and things to do around.