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Waukegan Holiday Rentals

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Holiday Rentals in Waukegan

Entire 3 Bedroom Cozy Unit

8.6 out of 10, Excellent, (7)
"This was one of the best places I have ever stayed. It was a gorgeous home, super clean and well appointed. The neighborhood was sweet and quiet. It was very close to the Great Lakes Navy Base for my sons graduation from boot camp. I live in San Diego and this area reminded me of home with a diverse selection of shops and restaurants and all different kinds of people and cultures. I felt safe and enjoyed walks around the neighborhood. The houses are very different than here in San Diego. I...
The price is AU$496
includes taxes & fees
3 Dec - 4 Dec
Entire 3 Bedroom Cozy Unit

Colorful 4-bedroom house-Vet owned-NAVAL Academy

10.0 out of 10, Exceptional, (1)
"Very close to the base for our daughters navy graduation. All the conveniences of home. Comfortable and inviting. Would definitely recommend especially for bootcamp graduation. "
Colorful 4-bedroom house-Vet owned-NAVAL Academy

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (57)
"I needed a place to stay for work. Thus lake house was well done! Cute, cozy and great views. The hosts were excellent and responded when needed. I will definitely be staying again when Im in the area!"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

Roxan Corner

8.4 out of 10, Very good, (29)
"Came to see my son graduate bootcamp"
Roxan Corner

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (231)
"I booked this property for a reunion with some old friends, with the intention that we would be spending a lot of time hanging out. This property was perfect for that -- lots of beds and bathrooms. A beautiful view of the lake from the main living area and two of the bedrooms. Lots of amenities/activities including a pool table, ping pong, a fire pit, etc. But perhaps the best feature was the openness of the kitchen/dining room/pool table/family room, which meant that you feel connected to...
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (36)
"This was an amazing property! We kept commenting how the house was so well designed to fully appreciate the beautiful lake. It was amazing! The living room, sun room, kitchen and dining room all took advantage of fantastic views. Though in a neighborhood, we felt like it was in the country. Everything was wonderful - from the beds to the space, to the views, to the quiet setting. Couldn't have been better! "
Beautiful and spacious lakefront home! Close to everything!

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

9.4 out of 10, Exceptional, (30)
"The spacious, well-maintained home was perfect for our group. The bedrooms were roomy, and the living areas provided plenty of space to relax and enjoy time together. The fully equipped kitchen made meal prep easy. A highlight was the neighboring estate with horses. The children loved it! The outdoor spaces were ideal for relaxation, with patios for morning coffee. Overall, this rental was the perfect setting for a memorable getaway. "
The price is AU$1,920
includes taxes & fees
3 Dec - 4 Dec
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

Comforting Retreat Near Woodfield Mall by RedAwning

9.4 out of 10, Exceptional, (10)
"Nice place to stay, will definitely stay again. "
Comforting Retreat Near Woodfield Mall by RedAwning

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.2 out of 10, Wonderful, (15)
"Close to everything for My Son Graduation . We where less then 5 Miles from the Navy Station. I like that We had 6 Beds for everyone could sleep. The Kitchen was perfect for cooking meals. "
New Your Home Away From Home! - Near Great Lakes Naval Base!!

Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds

9.2 out of 10, Wonderful, (7)
"Perfect location and weather. "
Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (56)
"Got to stay in this wonderful home while visiting my son and his family. I loved it!"
The price is AU$486
includes taxes & fees
3 Dec - 4 Dec
Quaint Bungalow, near Great Lakes Naval Base

Squeaky clean and cozy house, walk to AH downtown, fenced yard, pets, infants

9.8 out of 10, Exceptional, (9)
"Super clean home with modern updates. Definitely a bonus with the fenced in yard for the dog. Nice neighborhood to walk the dog and admire the Halloween decorations."
Squeaky clean and cozy house, walk to AH downtown, fenced yard, pets, infants

Private Get A Way

10.0 out of 10, Exceptional, (13)
"My family stayed here for four nights and we had a great experience. There was plenty of room in the kitchen and living room. The kitchen was well stocked for all our meals, and the bbq was a nice addition for steak night! We really enjoyed the hot tub as well, and the neighborhood was pretty quiet. Would definitely stay again! "
Private Get A Way

This is a VACATION spot with a million dollar view!

10.0 out of 10, Exceptional, (10)
"This house was beautiful. The view, WOW! My son has a pontoon docked a couple of miles away and was able to come and get us for a boat ride and lunch at Dockers. So fun. We spent a lot of time sitting on the deck in the sun. We had a wonderful stay. Thank You for sharing part of your life with us."
The price is AU$407
includes taxes & fees
3 Dec - 4 Dec
This is a VACATION spot with a million dollar view!

Peaceful and Relaxing Water Front Home with Outdoor Pool Sleeps 12

10.0 out of 10, Exceptional, (14)
"Three family’s came from 3 states for a wedding, and it was the perfect place for us to visit and enjoy one another! Thank you to the host who is terrific! "
Peaceful and Relaxing Water Front Home with Outdoor Pool Sleeps 12

Beautiful Spacious Escape On The Chain O'Lakes

9.4 out of 10, Exceptional, (55)
"Everyone enjoyed the view "
Beautiful Spacious Escape On The Chain O'Lakes

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (27)
"The property was great. It was exactly as described and the owner was available to answer any questions quickly. I stayed with my husband and 2 year old for the Fourth of July and the location was perfect for us. Right across the street from park and beach. Only problem we had was the grill wasn’t clean. We couldn’t use it, which was kind of a bummer since it was the 4th of July but not the end of the world. Would definitely stay here again. "
The price is AU$513
includes taxes & fees
3 Dec - 4 Dec
Lake/Beach Getaway (Remodeled)

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (20)
"There is a reason this property is so highly rated. First of all, from the time I reserved it, the owner was constantly in communication with me. Her directions were clear and she made herself available. When I arrived she was there making sure everything was in order. Her demeaner was kind and professional. The house is spacious and yes it is an older house, but the owner has done so many things to update it, we were very pleased. Finally, the cost was entirely reasonable. This was an all...
The price is AU$432
includes taxes & fees
7 Dec - 8 Dec
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

Lakefront Cottage with Gorgeous Sunsets

9.2 out of 10, Wonderful, (5)
"Simple, minimal, quaint cozy lake cottage with stunning views both day and night. Owner was very responsive and accommodating! Thanks for helping make our Christmas trip great."
Lakefront Cottage with Gorgeous Sunsets

Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed

10.0 out of 10, Exceptional, (74)
"First of all this lakeside home was breath taking and so very cozy. Everything we could have possibly needed we had available, beds were comfortable and the space was perfect for my small family visiting our son for his Naval boot camp graduation. Thank you Josh for opening your doors to us and allowing us to visit your home. It was perfect. "
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Waukegan you may be interested in

Sonesta ES Suites Chicago Waukegan Gurnee

3.0 star property
8.8 out of 10, Excellent, (1008)
"We came for bootcamp graduation! Check in was great. Extending our stay for 1 day was easy. Breakfast was good! Great location! "
The price is AU$158
includes taxes & fees
21 Dec - 22 Dec
Sonesta ES Suites Chicago Waukegan Gurnee

Holiday Inn Express & Suites Waukegan, an IHG Hotel

2.5 star property
8.6 out of 10, Excellent, (1001)
"All staff was so kind. It was very clean and offered a great hot breakfast. 5 stars!"
The price is AU$170
includes taxes & fees
24 Dec - 25 Dec
Holiday Inn Express & Suites Waukegan, an IHG Hotel

Courtyard Chicago Waukegan Gurnee

3.0 star property
9.2 out of 10, Wonderful, (1002)
"Really comfortable beds, spacious shower and the pool was fun! Great stay "
The price is AU$218
includes taxes & fees
8 Dec - 9 Dec
Courtyard Chicago Waukegan Gurnee
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Waukegan?

Yes, there are holiday rentals in Waukegan close to The People's Choice Family Fun Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the fun-filled theme parks and scenic lakeside in Waukegan. Make sure to also enjoy the array of shops and top-notch restaurants during your holiday.

What are some of the best holiday rentals that Waukegan has to offer?

Entire 3 Bedroom Cozy Unit: This highly rated holiday home rental in Waukegan is equipped with a selection of books, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Waukegan?

Expedia has 41 holiday rentals for your stay in Waukegan.

What can I see and do in Waukegan?

Cultural attractions include Genesee Theater and Three Brothers Theatre, whereas Lake Michigan and North Beach are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Waukegan Harbor and The Temporary by American Place.

What are holiday rentals like in Waukegan?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Waukegan. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family getaway.