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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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
The price is AED 400
AED 907 total
includes taxes & fees
6 Oct - 7 Oct
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.
The price is AED 407
AED 898 total
includes taxes & fees
30 Sep - 1 Oct
Cute & Cozy, 1bd Condo Apartment/townhouse
A kitchen counter with a coffee maker, a water dispenser, a knife block, and a Keurig coffee maker.

3. Greenwood Loft & Rooftop

Greenwood Loft & Rooftop
Waukegan
The price is AED 378
AED 898 total
includes taxes & fees
24 Oct - 25 Oct
Greenwood Loft & Rooftop
A well-lit patio area with a brick wall, a door, a bench, and potted plants.

4. The Rooftop - Haven!

The Rooftop - Haven!
Waukegan
The price is AED 400
AED 955 total
includes taxes & fees
5 Oct - 6 Oct
The Rooftop - Haven!
A kitchen with wooden cabinets, a black countertop, and a window.

5. 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.
The price is AED 1,469
AED 2,628 total
includes taxes & fees
5 Oct - 6 Oct
Beautiful and Cozy With 5 Bedrooms
A bedroom with a large bed, two bedside tables, and decorative wall mirrors.

6. 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, (29 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.
The price is AED 613
AED 1,382 total
includes taxes & fees
29 Oct - 30 Oct
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
A living room with a television on a stand, a potted plant, a glass coffee table, and a window with curtains.

7. 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.
The price is AED 463
AED 860 total
includes taxes & fees
2 Oct - 3 Oct
Apartment Attached to a 1900 historic Farm house
A living room with a green sofa, a glass coffee table, and a black and white striped rug.

8. 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.
The price is AED 496
AED 1,226 total
includes taxes & fees
30 Sep - 1 Oct
6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags
Interior

9. 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.
The price is AED 874
AED 2,028 total
includes taxes & fees
26 Oct - 27 Oct
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
A modern living room with dark hardwood floors, white sofas, a round mirror, and a dining area with a table and chairs.

10. 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.
The price is AED 1,376
AED 2,755 total
includes taxes & fees
4 Oct - 5 Oct
Great America Getaway | Sleeps 12 | Near Navy Base
A two-story house with a stone chimney, a front porch with steps, and a flag.

11. 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.
The price is AED 496
AED 1,226 total
includes taxes & fees
30 Sep - 1 Oct
Quaint Bungalow, near Great Lakes Naval Base
A spacious living room with a wooden floor, a dining area, and a kitchen in the background.

12. 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.
The price is AED 444
AED 2,883 total
includes taxes & fees
30 Sep - 1 Oct
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.

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

Salem Vacation Home w/ Dock: Steps to Paddock Lake
3.0 star property
Salem
The price is AED 599
AED 2,997 total
includes taxes & fees
30 Sep - 1 Oct
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.

14. Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (32 reviews)
"Beautiful atmosphere "
United States
Stephanie
The price is AED 514
AED 938 total
includes taxes & fees
21 Oct - 22 Oct
Wisconsin Treehouse Getaway!
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.
The price is AED 551
AED 891 total
includes taxes & fees
1 Oct - 2 Oct
Charming 2-bedroom Channel house and kayaks in Paddock Lake
An outdoor patio with a hot tub, wicker chairs, and a table.

16. 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.
The price is AED 878
AED 1,160 total
includes taxes & fees
12 Oct - 13 Oct
Hot Tub Retreats
An outdoor patio with a hot tub, wicker chairs, and a table.

17. 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.
The price is AED 841
AED 1,471 total
includes taxes & fees
1 Oct - 2 Oct
Tiny Home Retreat with hot tub
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.

18. 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.
The price is AED 1,634
AED 2,499 total
includes taxes & fees
13 Oct - 14 Oct
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
A compact kitchen with a dining area, a refrigerator, a sink, and a cabinet.

19. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Vernon Hills
The price is AED 414
AED 458 total
includes taxes & fees
6 Oct - 7 Oct
1 Queen Bed | Non-Smoking, Kitchen
A house by a lake with docked boats and a flag.

20. This is a VACATION spot with a million dollar view!

This is a VACATION spot with a million dollar view!
fox lake
9.8 out of 10, Exceptional, (34 reviews)
"Great location!! Beautiful place!!!"
United States
Jason C.
The price is AED 1,653
AED 2,312 total
includes taxes & fees
8 Oct - 9 Oct
This is a VACATION spot with a million dollar view!
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

Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

8/10 Good
"It has every thing one would want. Because of our age we don’t need the refrigerator on the floor."
John 2-night trip
Posted 9 hours ago
Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

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.