A sandy beach with waves and a flock of birds.

Winthrop Harbor Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winthrop Harbor holiday rentals

Living area

1. 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 HK$868
HK$2,000 total
includes taxes & fees
1 Sept - 2 Sept
Cute & Cozy, 1bd Condo Apartment/townhouse
Interior

2. 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 HK$3,136
HK$5,933 total
includes taxes & fees
3 Sept - 4 Sept
Beautiful and Cozy With 5 Bedrooms
Interior

3. 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 HK$988
HK$1,911 total
includes taxes & fees
8 Sept - 9 Sept
Apartment Attached to a 1900 historic Farm house
Interior

4. Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake

Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake
Beach Park
10.0 out of 10, Exceptional, (16 reviews)
"Great family house felt like a resorts for the kids "
United States
Michael B.
The price is HK$4,234
HK$11,292 total
includes taxes & fees
31 Aug - 1 Sept
Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake
Room

5. Spacious 27’ RV on horse farm

Spacious 27’ RV on horse farm
Bristol
8.8 out of 10, Excellent, (10 reviews)
"It was perfect for my husband, myself and my daughter during the 4th of July weekend! "
United States
Faith N.
The price is HK$706
HK$910 total
includes taxes & fees
31 Aug - 1 Sept
Spacious 27’ RV on horse farm
Interior

6. 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 HK$1,889
HK$4,661 total
includes taxes & fees
1 Sept - 2 Sept
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
Exterior detail

7. 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 HK$1,058
HK$2,800 total
includes taxes & fees
8 Sept - 9 Sept
Quaint Bungalow, near Great Lakes Naval Base
Outdoor dining

8. 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 HK$1,058
HK$1,745 total
includes taxes & fees
31 Aug - 1 Sept
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Private kitchen

9. 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
The price is HK$1,074
HK$4,847 total
includes taxes & fees
1 Sept - 2 Sept
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
Pool

10. 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 HK$1,176
HK$1,894 total
includes taxes & fees
31 Aug - 1 Sept
Marina Life II - 28 Carver @ Reef Point Marina
Interior

11. Irish Mist V @ Reefpoint Marina

Irish Mist V @ Reefpoint Marina
Racine
9.8 out of 10, Exceptional, (40 reviews)
"Nice spot to stay a night!"
United States
Joseph P.
The price is HK$1,058
HK$1,985 total
includes taxes & fees
31 Aug - 1 Sept
Irish Mist V @ Reefpoint Marina
Marina

12. 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, (30 reviews)
"Great location!! Beautiful place!!!"
United States
Jason C.
The price is HK$1,176
HK$2,376 total
includes taxes & fees
31 Aug - 1 Sept
This is a VACATION spot with a million dollar view!
Outdoor dining

13. 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 HK$1,874
HK$2,642 total
includes taxes & fees
31 Aug - 1 Sept
Hot Tub Retreats
Outdoor dining

14. Racine Canal retreat near Lake Michigan

Racine Canal retreat near Lake Michigan
Racine
Racine Canal retreat near Lake Michigan
Exterior

15. Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (32 reviews)
"Beautiful atmosphere "
United States
Stephanie
The price is HK$988
HK$1,949 total
includes taxes & fees
2 Sept - 3 Sept
Wisconsin Treehouse Getaway!
Living area

16. 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 HK$1,254
HK$2,084 total
includes taxes & fees
14 Sept - 15 Sept
Charming 2-bedroom Channel house and kayaks in Paddock Lake
Living area

17. 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 HK$1,505
HK$7,213 total
includes taxes & fees
31 Aug - 1 Sept
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Outdoor dining

18. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Chicago
10.0 out of 10, Exceptional, (14 reviews)
"Everything nice neat and clean"
United States
Anonymous traveller
The price is HK$775
HK$858 total
includes taxes & fees
6 Sept - 7 Sept
1 King Bed | Non-Smoking, Kitchen
Outdoor dining

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 HK$1,795
HK$3,349 total
includes taxes & fees
1 Sept - 2 Sept
Tiny Home Retreat with hot tub
Interior

20. 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 HK$1,897
HK$7,051 total
includes taxes & fees
31 Aug - 1 Sept
Salem Vacation Home w/ Dock: Steps to Paddock Lake
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

The Inn on Sheridan

The Inn on Sheridan

10/10 Excellent
"The entrance of the property needs to be cleaned I didn’t have a good first impression due to the patio area"
EARLINE 1-night trip
Posted 2 hours ago
The Inn on Sheridan

Find out more about Winthrop Harbor

Search for holiday rentals in Winthrop Harbor on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop Harbor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winthrop Harbor!

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.