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. Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Kenosha
9.4 out of 10, Exceptional, (96 reviews)
"Comfy, cozy, and clean place to stay!!"
United States
Erin
The price is NZ$205
includes taxes & fees
24 Aug - 25 Aug
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

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$440
includes taxes & fees
9 Sept - 10 Sept
Cute & Cozy, 1bd Condo Apartment/townhouse

3. Manor creek Vacation Getaway Navy Family home

Manor creek Vacation Getaway Navy Family home
Beach Park
9.6 out of 10, Exceptional, (4 reviews)
"House was super cute, very welcoming and spacious for our family and fur babies. Host was very responsive and allowed an early check in, last minute. Location was great, close to local stores. Couldnt have found a better home away from home for our stay. "
United States
Rachel N.
Manor creek Vacation Getaway Navy Family home

4. 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$1,240
includes taxes & fees
17 Sept - 18 Sept
Beautiful and Cozy With 5 Bedrooms

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$424
includes taxes & fees
18 Sept - 19 Sept
Apartment Attached to a 1900 historic Farm house

6. Greenbay Paradise-Navy 3 Mile Private Huge outdoor

Greenbay Paradise-Navy 3 Mile Private Huge outdoor
Beach Park
10.0 out of 10, Exceptional, (1 review)
"The bed space was perfect for my family. The game room is a nice touch. Played pool with my kids and they had a great time!"
United States
Eric H.
Greenbay Paradise-Navy 3 Mile Private Huge outdoor

7. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (74 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
The price is NZ$595
includes taxes & fees
12 Sept - 13 Sept
Quaint Bungalow, near Great Lakes Naval Base

8. 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$1,016
includes taxes & fees
8 Sept - 9 Sept
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

9. 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$433
includes taxes & fees
14 Sept - 15 Sept
Charming 2-bedroom Channel house and kayaks in Paddock Lake

10. Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen
Chicago
10.0 out of 10, Exceptional, (15 reviews)
"Big room with a kitchen,"
United States
Anonymous traveller
The price is NZ$174
includes taxes & fees
13 Sept - 14 Sept
Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

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)
"Was a nice little get away location. "
United States
Shanna D.
The price is NZ$1,481
includes taxes & fees
30 Aug - 31 Aug
Salem Vacation Home w/ Dock: Steps to Paddock Lake

12. Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19

Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Racine
9.6 out of 10, Exceptional, (18 reviews)
"Very nice stay. Bed was comfortable and clean. Liked the experience of being on a boat. Amenities were great. Had a little trouble with the on board toilet but otherwise it was a great stay."
United States
Carrie
The price is NZ$363
includes taxes & fees
30 Aug - 31 Aug
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19

13. Irish Mist V @ Reefpoint Marina

Irish Mist V @ Reefpoint Marina
Racine
9.8 out of 10, Exceptional, (39 reviews)
"Nice spot to stay a night!"
United States
Joseph P.
The price is NZ$423
includes taxes & fees
24 Aug - 25 Aug
Irish Mist V @ Reefpoint Marina

14. Marina Life II - 28 Carver @ Reef Point Marina

Marina Life II - 28 Carver @ Reef Point Marina
Racine
9.6 out of 10, Exceptional, (55 reviews)
"Great value for an amazing location!"
United States
Douglas E.
The price is NZ$394
includes taxes & fees
18 Sept - 19 Sept
Marina Life II - 28 Carver @ Reef Point Marina

15. Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (32 reviews)
"Beautiful atmosphere "
United States
Stephanie
The price is NZ$404
includes taxes & fees
1 Sept - 2 Sept
Wisconsin Treehouse Getaway!

16. Hot Tub Retreats

Hot Tub Retreats
Lake Villa
10.0 out of 10, Exceptional, (1 review)
"Very clean and cozy I loved my stay"
United States
Rosilynn B.
The price is NZ$549
includes taxes & fees
30 Aug - 31 Aug
Hot Tub Retreats

17. Racine Canal retreat near Lake Michigan

Racine Canal retreat near Lake Michigan
Racine
The price is NZ$410
includes taxes & fees
1 Sept - 2 Sept
Racine Canal retreat near Lake Michigan

18. 3-bedroom vacation home just a short walk to Lake Michigan

3-bedroom vacation home just a short walk to Lake Michigan
Racine
9.0 out of 10, Wonderful, (40 reviews)
"Amazing location. Easy parking and entrance. Wish i was there in the summer. Would definitely stay again"
United States
Michelle C.
The price is NZ$454
includes taxes & fees
28 Aug - 29 Aug
3-bedroom vacation home just a short walk to Lake Michigan

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$713
includes taxes & fees
31 Aug - 1 Sept
Tiny Home Retreat with hot tub
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 North Point Marina Beach 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.