Holiday rentals in Waukegan

4.77 out of 5 average rating, 62 reviews

Home in Beach Park

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

4.98 out of 5 average rating, 221 reviews

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.

4.89 out of 5 average rating, 200 reviews

Guest suite in Zion

Non-smoking, attached mother-in-law suite.

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 7PM.

Guest suite in Riverwoods

4.96 out of 5 average rating, 399 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

4.83 out of 5 average rating, 100 reviews

Tiny home in Beach Park

Tiny home in not so tiny Yard

The house has a Queen bed, a Single bed and a sofa. A tiny home in a peaceful neighborhood. Built on 4 city lots, it has plenty of space and privacy. For families visiting the Naval Academy, we are close enough, yet give you space and privacy. Away from the hustle of North Chicago and Waukegan. Nearby attractions are: Naval Base - 11 miles, 20 minutes Six Flags - 7 miles, 15 minutes Illinois State Beach - 2 miles, 5 minutes Chicago - 46 miles, 60 minutes Milwaukee - 50 miles, 55 minutes

4.92 out of 5 average rating, 124 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!

4.82 out of 5 average rating, 134 reviews

Flat in Waukegan

Cozy Corner, stylish 1bed near Navy Base!

Kick back and relax in this calm, stylish space. This is a newly remodeled 1 bedroom apartment. The Cozy Corner is designed to be a place of peace, for rest and relaxation. Feel right at home in this beautiful apartment. The kitchen is stocked with plenty of utensils and cookware for your favorite meal. Be sure to relax by the indoor fireplace and watch your favorite movies. Dedicated work space with desk and fast wifi perfect for traveling professionals. Longer stays discounted!

4.86 out of 5 average rating, 131 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.

4.99 out of 5 average rating, 150 reviews

Home in Round Lake Beach

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!

4.93 out of 5 average rating, 70 reviews

The Oak Tree Ranch

This Mid-Century Modern Ranch home features a large White Oak Tree that gracefully shades this beautifully updated home! We are located just 13 minutes from the Great Lakes Naval Station and this is the perfect location to celebrate your loved one's graduation from Boot Camp, as well as enjoy all the wonderful places and sights in the Chicagoland area. You'll love the large floor-to-ceiling windows and all the unique MCM furniture in this lovely home.

4.96 out of 5 average rating, 24 reviews

Flat in Waukegan

Cozy Apartment | Naval Station | Six Flags

Surround yourself with style in this standout space. Our home includes full furnished kitchen, WiFi, and new flooring! BEDROOM / LIVING ROOM 1 Queen size bed 2 Sofa beds TV Shelf Space Dedicated workspace Fresh clean linens KITCHEN & DINING Microwave Oven Stove Refrigerator/Freezer Coffee Maker + Coffee essentials Sink Trays Glasses Silverware Pots BATHROOM Bath with a Shower Mirror Toilet Towels Essentials Toiletries

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Other great holiday rentals in Waukegan

4.94 out of 5 average rating, 89 reviews

Private room in Zion

4. Cozy 2-Bedroom Modern Haven

ChanelRating, 5 stars1 day ago

Maria's house was a dream! Very lovely, very clean, very quiet. I enjoyed my stay immensely in the attic space. If I'm ever back that way, I would stay at her place again!

4.91 out of 5 average rating, 104 reviews

Private room in Evanston

Room Mins to Downtown Chicago & Northwestern!

NataliaRating, 5 stars6 days ago

Musa was very friendly and helpful the entire time we stayed at his place. The house is big, neat and located in a nice and calm neighbourhood, ideal if you want to rest after a day in downtown. Good shops nearby so I recommend go for a walk around the beautiful Evanston.

4.8 out of 5 average rating, 362 reviews

Hotel room in Itasca

King Bed at Chicago Northwest + PET Friendly

ShayRating, 5 stars3 weeks ago

I’ve stayed here several times and have always enjoyed myself. Terrific value. Thanks for hosting.

5 out of 5 average rating, 8 reviews

Historical Hideaway Near Naval Base

KeriRating, 5 stars2 weeks ago

We had such a great experience in Emily's home. We were blown away by the place , it was everything we wanted and more. This was our first experience in an Air bnb, so has made a very good impression on this service. We stayed here for our son's bootcamp graduation and it was the perfect location. Close to the train station if you want to commute to Chicago, a lovely beach nearby, a large mall etc., and most importantly a 10-15 minite drive to the Navy Base, everything you could possibly need but still tucked away in the sweetest historic neighborhood. we absolutely loved it and can't wait to book it again to visit him in A school. The house itself was clean, very tastefully decorated, and had very comfy beds! our son loved the master bed! On top of that many amenities were supplied, coffee machine, laundry, games etc. Thank you for being such a great host Emily. If your place is available we will definitely book again!

Hotel room in Libertyville

4.84 out of 5 average rating, 44 reviews

Spacious Budget-friendly Room w/ Kitchenette

KaidenRating, 5 stars2 weeks ago

Easy check in, super clean room with a nice bathroom, 24 hour access to the snack bar downstairs and checkin/checkout; overall a GREAT stay and well worth the price!

4.93 out of 5 average rating, 288 reviews

Flat in Winthrop Harbor

Like coming home plus special details

RebeccaRating, 5 stars2 weeks ago

I can’t explain how wonderful this airbnb experience was!! I was visiting Great Lakes for my boyfriend’s navy bootcamp graduation and it was a quick 25 mins away. Great location, easy access, and beautiful scenery. Allison provided so many little snacks, drinks, travel size bottles for anything you might’ve forgotten to pack. Allison was quick with responding to any questions I had, and she has been the best Airbnb host I’ve ever had. I would recommend booking with Allison! I will book here if i’m ever in town again.

5 out of 5 average rating, 5 reviews

Great Lakes Family Getaway

VictorRating, 5 stars2 weeks ago

I have rented many properties over the years for family vacations, reunions and leisure. Sandra’s property stood out from many others due to how clean, new and newly remodeled everything was. There is a golf course right in the backyard, the home is cozy and perfect for entertaining my group of 8 adults. We were in town to attend my brother’s Navy boot camp graduation and we all had a great time. The kitchen is brand new and has great appliances to include an oven that is able to air fry. I had no problem baking my brother his favorite cheesecake, as the kitchen is well stocked. Located super close to Target and a grocery store. We will defiantly be renting this property again if we are in the Chicago/Great Lakes area again. Sandra was super attentive and responsive. She made great recommendations and was very accommodating to our family.