Winthrop Harbor Holiday Rentals

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Holiday Rentals in Winthrop Harbor

Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
6.8 out of 10, (5)
"The home is very cute, nice location, and overall was fine for what we needed. We were in town for a wedding and needed a dog friendly place where he could hang while we were gone, and basically just a place to crash. The host was very responsive and let us check in early which was so helpful. The fenced in yard was great! But, it wasn’t the cleanest place I’ve ever stayed. The tub had bugs in it and was definitely dirty. Thankfully we didn’t need to use it but if we had, I would’ve had to clean...
The price is AU$505
includes taxes & fees
29 Sept - 30 Sept
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
New Humble Home! - Near Six Flags & Naval Base!!
9.0 out of 10, Wonderful, (21)
"The home is very close to base and was clean. The stairs to the second floor are old and not straight which can be a hazard. It worked for what we needed."
New Humble Home! - Near Six Flags & Naval Base!!
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
10.0 out of 10, Exceptional, (227)
"The lake was a big draw, along with six bedrooms. We love to check out the town, shop a little, hike and eat lunch out, spending the rest of the time being together and playing games. Plenty of room in the house, with a beautiful view. Enjoyed watching the sunrise both on the deck and patio."
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.4 out of 10, Exceptional, (15)
"The place was clean and had everything as advertised. IT was real close to Navy Graduation which was our primary goal. The back porch was nice too."
The price is AU$420
includes taxes & fees
29 Sept - 30 Sept
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Roxan Corner
8.6 out of 10, Excellent, (25)
"The pics did not mislead. It was nice and roomy for my guests and I. It could’ve been cleaner but overall enjoyed the house"
Roxan Corner
Riverfront Libertyville Retreat w/ Outdoor Kitchen
8.4 out of 10, Very good, (11)
"Location is wonderful if you are celebrating your Sailor's graduation. It's about 13 minutes away from base, however, traffic gets crazy around base so you still have to leave really early. The house itself is in a great location. The neighborhood is super quiet and we felt completely safe. The only negative thing I would have to say is that there is only 1 TV in the house that runs off WiFi and 2 of the 3 showers handle was broken, so it took us a minute to figure out you just had to turn it....
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, (55)
"Nice clean home with a great view. It was wonderful to have laundry on site. And the house had everything we needed from towels to cooking supplies to water, coffee and snacks. And the water pressure and mattresses were great! We slept so well! The neighborhood was nice and quiet. I do think it could be a little cuter. But they are working on it. There is a brand new park area that’s beautiful and a great nearby place to rent any boat you might want. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (54)
"With my daughter moving back to Illinois, we needed to help her get acclimated back to school. As former residence of Illinois, we still have plenty of family and friends that reside there and needed a good central location to stay. Hotels are overrated and just inconvenient. This little charming gem in the northern Of Chicago and was able to call at home for four nights. Super cute bungalow in a fabulous walkable distance to restaurants and shops, centrally located to amazing shopping. The...
The price is AU$462
includes taxes & fees
1 Oct - 2 Oct
Quaint Bungalow, near Great Lakes Naval Base
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes
9.4 out of 10, Exceptional, (59)
"Excellent"
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
10.0 out of 10, Exceptional, (69)
"We enjoyed our trip to Illinois. The accommodations were comfortable and just as described. "
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
9.8 out of 10, Exceptional, (18)
"Love the location. The owner even decorated for us as we were coming in for our son’s Navy graduation. Highly recommend this home. "
The price is AU$1,031
includes taxes & fees
22 Oct - 23 Oct
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
Modern living & Walk to downtown Libertyville ★ Great for Navy Graduations
9.4 out of 10, Exceptional, (6)
"From our initial booking until check- out all questions/requests were promptly addressed and completed. The set-up in the residence totally fit our needs. Would repeat this listing if the whole family comes back. "
Modern living & Walk to downtown Libertyville ★ Great for Navy Graduations
Entire 3 Bedroom Cozy Unit
8.0 out of 10, Very good, (5)
"The rental was ok the host was really nice but if you plan on going out to downtown Chicago or any attractions the drive to get around the city will take about an hour and a half every day unless it’s nighttime… only thing u are close to at this location is six flags but other than that safe quiet area an the host lives down stairs from where u will be staying don’t know if that’s a good or bad for you an your guess but hey.. but it was cool for my first time in Chicago but I wouldn’t go back to...
The price is AU$470
includes taxes & fees
29 Sept - 30 Sept
Entire 3 Bedroom Cozy Unit
Lake/Beach Getaway (Remodeled)
10.0 out of 10, Exceptional, (22)
"The house was perfect for us as we were visiting family in the area. House was very clean and comfortable and had everything we needed for our stay. Lake view in the morning was quite relaxing. Would stay here again. "
The price is AU$326
includes taxes & fees
29 Sept - 30 Sept
Lake/Beach Getaway (Remodeled)
Enjoy Beachfront Living With family!
9.8 out of 10, Exceptional, (66)
"What a beautiful house and right across from the lake. Plenty of room for the 9 of us tp spread out if we wanted."
Enjoy Beachfront Living With family!
Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds
8.8 out of 10, Excellent, (5)
"Good location. Fun toys for the lake, plenty of space. My only complaints, was fire pit on right side had garbage in it. I cleaned out. The black stone was not cleaned. Again we left in better condition but should be checked. We definitely needed a whisk! We were going to buy one for you but didn’t remember."
Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds
Private Get A Way
10.0 out of 10, Exceptional, (10)
"8 of us traveled from across the country to see my son graduate from Navy Bootcamp, and this house was perfection! The pictures and description on Bebo don’t do it justice. It was so wonderful to have a comfortable place to hang out with my son, so much better than a hotel. We were able to sit outside at night and enjoy the gas fire pit, play football in the spacious private backyard, and eat family meals to gather again in the stocked kitchen. Any questions I had were answered within minutes by...
Private Get A Way
This is a VACATION spot with a million dollar view!
10.0 out of 10, Exceptional, (8)
"Loved sitting both on the deck and inside to enjoy the incredible view! Great location."
The price is AU$516
includes taxes & fees
1 Oct - 2 Oct
This is a VACATION spot with a million dollar view!
Sunset Cottage on Lake Pistakee
9.6 out of 10, Exceptional, (66)
"Great location close to where we were going. Nice views all the comforts of home. Thank you we will be back "
Sunset Cottage on Lake Pistakee
IVP Manor House Close to Lake Beach & Naval Base
9.6 out of 10, Exceptional, (49)
"This was the second time we stayed at this location for an annual trip to great America. It was everything we needed! Very clean! Communication from host was exceptional."
IVP Manor House Close to Lake Beach & Naval Base
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Other types of properties in Winthrop Harbor you may be interested in

La Quinta Inn & Suites by Wyndham Chicago Gurnee
2.5 star property
7.6 out of 10, Good, (1007)
"They accomplished making my vacation worth it. The staff was remarkable. They genuinely cared about my feelings, what was going on in my life. They appreciated my excitement for me being there, and went above and beyond. Will be going back!"
The price is AU$90
includes taxes & fees
30 Sept - 1 Oct
La Quinta Inn & Suites by Wyndham Chicago Gurnee
Best Western Executive Inn Kenosha/Pleasant Prairie
2.5 star property
9.0 out of 10, Wonderful, (1006)
"The room was clean, very comfortable bed and the towels were so plush and soft. The staff was very accommodating and the breakfast was great. Hot food was hot and coffee was so good also. Highly recommended."
The price is AU$119
includes taxes & fees
8 Oct - 9 Oct
Best Western Executive Inn Kenosha/Pleasant Prairie
Wingate by Wyndham Gurnee
2.5 star property
8.8 out of 10, Excellent, (1001)
"Staff members were very professional…quick & easy check in."
The price is AU$139
includes taxes & fees
1 Oct - 2 Oct
Wingate by Wyndham Gurnee
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.

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?

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families : This holiday home rental outside of Winthrop Harbor has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Winthrop Harbor?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Winthrop Harbor stay.

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. You’ll find favourite places to visit such as Naval Base Great Lakes and Six Flags Great America in the wider area.

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.