A sandy beach with waves and a flock of birds.

Winthrop Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winthrop Harbor vacation rentals

A modern living room with a sofa, a blue armchair, a coffee table, and a TV mounted on the wall.

1. The Beach Park Retreat

The Beach Park Retreat
Beach Park
10.0 out of 10, Exceptional, (1 review)
"The host, Hugo, was friendly and answered questions promptly, the apartment was spacious and well maintained. The kitchen had everything we needed for a weekend trip. I would recommend this property to anyone staying in the area."
United States
Sara
$232 nightly
The price is $255
Oct 13 - Oct 14
Total with taxes and fees
The Beach Park Retreat
A living room with a sofa, coffee table, lamp, and a staircase.

2. Cute & Cozy, 1bd Condo Apartment/townhouse

Cute & Cozy, 1bd Condo Apartment/townhouse
Zion
9.6 out of 10, Exceptional, (4 reviews)
"Great stay was clean and in a great location overall was a good experience!"
United States
Tristan P.
$237 nightly
The price is $251
Oct 10 - Oct 11
Total with taxes and fees
Cute & Cozy, 1bd Condo Apartment/townhouse
A kitchen with wooden cabinets, a black countertop, and a window.

3. Beautiful and Cozy With 5 Bedrooms

Beautiful and Cozy With 5 Bedrooms
Zion
8.8 out of 10, Excellent, (23 reviews)
"This is a great home with plenty of space!"
United States
randy w.
$714 nightly
The price is $757
Oct 17 - Oct 18
Total with taxes and fees
Beautiful and Cozy With 5 Bedrooms
A well-lit patio area with a brick wall, a door, a bench, and potted plants.

4. The Rooftop - Haven!

The Rooftop - Haven!
Waukegan
$244 nightly
The price is $271
Oct 18 - Oct 19
Total with taxes and fees
The Rooftop - Haven!
A kitchen counter with a coffee maker, a water dispenser, a knife block, and a Keurig coffee maker.

5. Greenwood Loft & Rooftop

Greenwood Loft & Rooftop
Waukegan
$233 nightly
The price is $259
Oct 20 - Oct 21
Total with taxes and fees
Greenwood Loft & Rooftop
A living room with a television on a stand, a potted plant, a glass coffee table, and a window with curtains.

6. Apartment Attached to a 1900 historic Farm house

Apartment Attached to a 1900 historic Farm house
Old Mill Creek
8.6 out of 10, Excellent, (20 reviews)
"The place is very cozy and inviting. There was a smell we thought might have been cat urine on a blanket. Otherwise I'd recommend it."
United States
Matt H.
$227 nightly
The price is $241
Oct 11 - Oct 12
Total with taxes and fees
Apartment Attached to a 1900 historic Farm house
A bedroom with a large bed, two bedside tables, and decorative wall mirrors.

7. 3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Waukegan
9.4 out of 10, Exceptional, (30 reviews)
"Excellent location for Navy Graduation and clean. 5 minutes to the Metra Train. Property owner is very responsive and flexible. Beds were comfortable and double sink in the 1 bathroom was a plus."
United States
Shannon W.
$345 nightly
The price is $384
Nov 1 - Nov 2
Total with taxes and fees
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
A modern living room with dark hardwood floors, white sofas, a round mirror, and a dining area with a table and chairs.

8. Great America Getaway | Sleeps 12 | Near Navy Base

Great America Getaway | Sleeps 12 | Near Navy Base
Gurnee
10.0 out of 10, Exceptional, (1 review)
"Lovely place"
United States
Jack E.
$653 nightly
The price is $724
Oct 12 - Oct 13
Total with taxes and fees
Great America Getaway | Sleeps 12 | Near Navy Base
A two-story house with a stone chimney, a front porch with steps, and a flag.

9. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (75 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
$333 nightly
The price is $353
Oct 11 - Oct 12
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base
A kitchen shelf with three white pots with lids, each with a wooden handle.

10. 6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags

6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags
Waukegan
10.0 out of 10, Exceptional, (1 review)
"Great place for overnight stay. Plenty of room for family of 7. Way better than staying at a hotel."
United States
Kim K.
$334 nightly
The price is $354
Oct 11 - Oct 12
Total with taxes and fees
6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags
A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

11. Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Chicago
9.6 out of 10, Exceptional, (17 reviews)
"Great place to stay"
United States
Anonymous traveler
$67 nightly
The price is $74
Oct 18 - Oct 19
Total with taxes and fees
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen
Interior

12. Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
North Chicago
7.8 out of 10, Good, (6 reviews)
"Rented this property for my sons navy graduation, Base was only 6 minutes from the home. Tons of places to eat and shop no more then 15 minutes away. The house was super cute, very clean. we flew in at 10am and without even having to ask the host reached out and let us know it was ready for check in a few hours early which was great. left some packaged up congrats grad decor that hopefully didnt get thrown out and the next navy fam can use. "
United States
Linda U.
$544 nightly
The price is $577
Nov 2 - Nov 3
Total with taxes and fees
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
A modern living room with a grey sofa, a grey ottoman, and a coffee table. There are large windows with curtains, a flat-screen TV mounted on the wall, and decorative wall art.

13. Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls

Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
Gurnee
9.4 out of 10, Exceptional, (43 reviews)
"Great space for the kids and adults.The pool table was very popular. Located close to the Great Lakes Naval Station so it was convenient to pickup/drop off our Sailor during liberty. Host was very accommodating and great in making sure we had a good experience."
United States
Jim L.
$680 nightly
The price is $721
Oct 19 - Oct 20
Total with taxes and fees
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
An outdoor patio with a hot tub, wicker chairs, and a table.

14. Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub
Lake Villa
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
$402 nightly
The price is $426
Oct 13 - Oct 14
Total with taxes and fees
Tiny Home Retreat with hot tub
A modern living space with a kitchen, dining area, and a cozy seating area.

15. Charming 2-bedroom Channel house and kayaks in Paddock Lake

Charming 2-bedroom Channel house and kayaks in Paddock Lake
Salem
10.0 out of 10, Exceptional, (13 reviews)
"Excellent property and location!"
United States
Rod L.
$240 nightly
The price is $253
Nov 2 - Nov 3
Total with taxes and fees
Charming 2-bedroom Channel house and kayaks in Paddock Lake
A spacious living room with a wooden floor, a dining area, and a kitchen in the background.

16. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem Vacation Home w/ Dock: Steps to Paddock Lake
Salem
9.2 out of 10, Wonderful, (11 reviews)
"Was a nice little get away location. "
United States
Shanna D.
$791 nightly
The price is $835
Oct 17 - Oct 18
Total with taxes and fees
Salem Vacation Home w/ Dock: Steps to Paddock Lake
A spacious living room with a wooden floor, a dining area, and a kitchen in the background.

17. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem Vacation Home w/ Dock: Steps to Paddock Lake
3.0 star property
Salem
$773 nightly
The price is $816
Oct 17 - Oct 18
Total with taxes and fees
Salem Vacation Home w/ Dock: Steps to Paddock Lake
A glass-enclosed gazebo with a metal roof, wooden deck, and a statue of a person.

18. Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (32 reviews)
"Beautiful atmosphere "
United States
Stephanie
$219 nightly
The price is $249
Oct 12 - Oct 13
Total with taxes and fees
Wisconsin Treehouse Getaway!
An outdoor patio with a hot tub, wicker chairs, and a table.

19. Hot Tub Retreats

Hot Tub Retreats
Lake Villa
6.0 out of 10, (2 reviews)
"Very disgusting wanted us to throw our poop paper in a waste basket and not flush it down the toilet told me that the previous people that rented took off with the key never changed the locks. Just had to deal with it. Very bad poor communication no information prior to arriving worst place ever."
United States
April R.
$316 nightly
The price is $335
Oct 12 - Oct 13
Total with taxes and fees
Hot Tub Retreats
An outdoor patio with brick flooring, a grill, and a table with chairs.

20. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Chicago
9.0 out of 10, Wonderful, (16 reviews)
"Everything nice neat and clean"
United States
Anonymous traveler
$71 nightly
The price is $79
Oct 18 - Oct 19
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen
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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Top Winthrop Harbor Hotel Reviews

Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

8/10 Good
"The hotel was in an optimal location for our needs. The room was spacious, comfortable, and clean, although the corridors leading to the room needed a good vacuuming. The breakfast area was very crowded and all the seating was in use. The food was good, but they had a hard time keeping it well-stocked. Coffee and sausage stations were emptied of their respective products. Milk carafewas empty. Eventually, they were stocked again, but it appeared to be challenging to keep it all filled with the large crowd. Still, our one night stay here was exactly what we needed at exactly the right time and location and cost. We will stay here again."
Mary 1-night trip
Posted 7 hours ago
Sonesta ES Suites Chicago Waukegan Gurnee

Find out more about Winthrop Harbor

Everything you need to know about Winthrop Harbor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop Harbor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winthrop Harbor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop Harbor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winthrop Harbor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winthrop Harbor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $85 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop Harbor rentals

At Expedia, we put the best Winthrop Harbor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winthrop Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winthrop Harbor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winthrop Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Winthrop Harbor?

Yes, you can find vacation rentals where you'll be just 9.5 mi (15.3 km) from Six Flags Great America, giving you a secluded option to escape the hustle and bustle. Winthrop Harbor is known for its beaches and restaurants.

What are some of the best vacation rentals in Winthrop Harbor?

Pleasant 3-bedroom house with occupied basement separate entrance.: This vacation home rental outside of Winthrop Harbor has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What’s there to see and do in Winthrop Harbor?

Lake Michigan and Spring Bluff Forest Preserve are a couple of lovely local spots to get outside and enjoy nature. While here, North Point Marina and Winthrop Harbor Village Hall are other places worth a visit.

What’s a vacation rental in Winthrop Harbor like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Winthrop Harbor. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.