A sandy beach with waves and a flock of birds.

Winthrop Harbor Holiday Rentals

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Our top choices for Winthrop Harbor holiday rentals

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 NZ$457
includes taxes & fees
6 Oct - 7 Oct
The Beach Park Retreat

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 NZ$477
includes taxes & fees
11 Oct - 12 Oct
Cute & Cozy, 1bd Condo Apartment/townhouse

3. Greenwood Loft & Rooftop

Greenwood Loft & Rooftop
Waukegan
The price is NZ$459
includes taxes & fees
20 Oct - 21 Oct
Greenwood Loft & Rooftop

4. The Rooftop - Haven!

The Rooftop - Haven!
Waukegan
The Rooftop - Haven!

5. 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 NZ$434
includes taxes & fees
6 Oct - 7 Oct
Apartment Attached to a 1900 historic Farm house

6. 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 NZ$1,304
includes taxes & fees
14 Oct - 15 Oct
Beautiful and Cozy With 5 Bedrooms

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.
The price is NZ$692
includes taxes & fees
1 Nov - 2 Nov
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

8. 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 traveller
The price is NZ$136
includes taxes & fees
19 Oct - 20 Oct
Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

9. 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 NZ$596
includes taxes & fees
6 Oct - 7 Oct
6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags

10. 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 NZ$623
includes taxes & fees
6 Oct - 7 Oct
Quaint Bungalow, near Great Lakes Naval Base

11. 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)
"Property matched the listing exactly. Will be staying again!"
United States
Alec M.
The price is NZ$1,424
includes taxes & fees
17 Oct - 18 Oct
Salem Vacation Home w/ Dock: Steps to Paddock Lake

12. 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 NZ$1,280
includes taxes & fees
13 Oct - 14 Oct
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls

13. 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 NZ$1,366
includes taxes & fees
12 Oct - 13 Oct
Great America Getaway | Sleeps 12 | Near Navy Base

14. Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (32 reviews)
"Beautiful atmosphere "
United States
Stephanie
The price is NZ$467
includes taxes & fees
21 Oct - 22 Oct
Wisconsin Treehouse Getaway!

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 NZ$440
includes taxes & fees
12 Oct - 13 Oct
Charming 2-bedroom Channel house and kayaks in Paddock Lake

16. Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
Libertyville
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

17. 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 NZ$1,000
includes taxes & fees
4 Nov - 5 Nov
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

18. 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 NZ$1,453
includes taxes & fees
17 Oct - 18 Oct
Salem Vacation Home w/ Dock: Steps to Paddock Lake

19. 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 NZ$683
includes taxes & fees
6 Oct - 7 Oct
Tiny Home Retreat with hot tub

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 traveller
The price is NZ$144
includes taxes & fees
19 Oct - 20 Oct
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

Find out more about Winthrop Harbor

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winthrop Harbor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winthrop Harbor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winthrop Harbor. Seeing all the best attractions is bound to make you fall in love with Winthrop Harbor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winthrop Harbor short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Winthrop Harbor?

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

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

Pleasant 3-bedroom house with occupied basement separate entrance.: This holiday 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 holiday rental in Winthrop Harbor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winthrop Harbor. Holiday rentals offer extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family getaway.