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, 3 reviews
"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$525
per night
20 June - 21 June
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, 8 reviews
"The proximity to Great Lakes Recruitment Center, Sarge’s Meet & Greet, restaurants, etc. is perfect. We were in town for our son’s boot camp graduation and knew we wanted more room to hang out than a typical hotel room would offer. It was great to be able to relax, watch movies, just hang out with our sailor for the precious two days we had. This place has location, location, location if you’re coming in for boot camp graduation."
The price is AU$398
per night
25 June - 26 June
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, 42 reviews
"We loved our stay at Cora Cottage. Everything was so beautifully decorated and clean. My husband and I appreciated all the small touches that welcomed us during our stay. We will definitely be coming back"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Roxan Corner
8.8 out of 10, Excellent, 19 reviews
"This duplex was perfect for my three sons and myself. We stayed five days to attend one of my son’s Navy Graduation! House was very clean and modern. Had everything we needed, was a nice neighborhood, quiet neighbors? Close to everywhere we needed to go. Only suggestion would be to have the owners secure the rugs, they are very slippery. "
Roxan Corner
Unique and Charming Private Quarters
10.0 out of 10, Exceptional, 36 reviews
"Sandy was so sweet, we enjoyed staying with her. Her cats were also a joy! The space is very comfortable, and the garden is lovely to have dinner in, but the space isn't completely separate. Everywhere you look, there is another beautiful mural or artwork that Sandy has created!"
The price is AU$164
per night
23 June - 24 June
Unique and Charming Private Quarters
Pistakee Marina Boat House
10.0 out of 10, Exceptional, 3 reviews
"We brought our boat to the chain o lakes with family. This house was perfect for us. We were able to use the fire pit and gas grill. The house was on the water so we were able to have access to the boat the entire stay. There is a restaurant next door to the house as well. Very quiet neighborhood too. Will stay here again!!"
Pistakee Marina Boat House
Beautiful and spacious lakefront home! Close to everything!
9.8 out of 10, Exceptional, 26 reviews
"Great stay in Antioch! Hope to visit again!"
Beautiful and spacious lakefront home! Close to everything!
Pet-Friendly Hotel Suite! Laundry & Outdoor BBQ Grill, Near Independence Grove Dog Park
4.0 out of 10, 1 review
"I left early to get another hotel."
The price is AU$213
per night
1 July - 2 July
Pet-Friendly Hotel Suite! Laundry & Outdoor BBQ Grill, Near Independence Grove Dog Park
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.4 out of 10, Exceptional, 12 reviews
"Its comfy family house.Near in Naval base,super market and restaurant. Well recommended to stay for graduation or vacation. The owner is fast to communicate. Our overall stay is ❤️.Thank you so much💕💕💕"
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Pet Friendly Huge Lake Front Home with Stunning Views
9.8 out of 10, Exceptional, 40 reviews
"Our stay was quiet and cozy for our new Navy graduate fresh from bootcamp. It was important to her to have a nice low key stay without a lot of activity surrounding her. We were even able to extend one more day to be able to spend extra time with her."
Pet Friendly Huge Lake Front Home with Stunning Views
Historic house on tree lined red brick street of historic homes.
10.0 out of 10, Exceptional, 19 reviews
"The house is well situated, just minutes from the lake and Main Street. We felt completely at home; the owners have decorated and appointed the house beautifully - every detail has been considered and implemented. Communication was easy and they solved issues (i.e. getting the drive shovelled in a snow storm) before we could even ask about them. The back porch and yard are wonderful for relaxing. We loved the house and the neighbourhood and found it difficult to leave!"
Historic house on tree lined red brick street of historic homes.
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
7.6 out of 10, Good, 11 reviews
"Poor communication except when they asked me to leave early so the cleaner could come in. He told me the app to download to access the house, but gave absolutely no instructions how that was to be done. Tack paper commonly used for the bottoms of drawers was used to cover the kitchen countertops, broken windows, hot upstairs, 2 wash rags and few towels, no laundry detergent, no soap, TV’s did not work, it goes on. I’m not writing this to be mean, I am writing this as feedback to the owner and...
The price is AU$372
per night
27 June - 28 June
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
Private Get A Way
10.0 out of 10, Exceptional, 8 reviews
"Our stay was amazing. Beautiful, peaceful and clean house. Would love to stay again in the future."
Private Get A Way
Entire 3 Bedroom Cozy Unit
10.0 out of 10, Exceptional, 3 reviews
"Came for Navy event and had a good night's rest"
The price is AU$485
per night
25 June - 26 June
Entire 3 Bedroom Cozy Unit
Fully Updated home. Great for the entire family!
7.6 out of 10, Good, 10 reviews
"My impression of the inside was good. However the outside needs some work. Maybe some up grades in the furniture would be beneficial. Other then that it was an enjoyable experience Thank u"
Fully Updated home. Great for the entire family!
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
10.0 out of 10, Exceptional, 221 reviews
"The property was beautiful! I just loved watching the sunrise every morning from the master bedroom! The only suggestion I have is to put in writing, in the rules book or a little sign by the refrigerator, how sensitive stainless steel is for those who do not own any stainless steel appliances."
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Lakefront Home w/ Game Room, Theater & Dock!
9.8 out of 10, Exceptional, 16 reviews
"Great place, we really enjoyed the place and location."
Lakefront Home w/ Game Room, Theater & Dock!
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, 47 reviews
"Great location, floor plan, water pressure, all the things were well thought out and convenient. Will stay again."
The price is AU$473
per night
24 June - 25 June
Quaint Bungalow, near Great Lakes Naval Base
Modern Luxe home w/Gameroom and Electric Fireplace
8.4 out of 10, Very good, 6 reviews
"We really loved our stay at this house with group of our friends. This place was just perfect, newly renovated and exactly looked like it is in pictures. The house has everything needed from games in basement to the cozy beds to rest at night. Host was incredibly responsive and made us feel right at home. Recommended nearby places to explore and we had a great getaway overall. I would stay here again when in town. 10/10!!"
Modern Luxe home w/Gameroom and Electric Fireplace
Lake/Beach Getaway (Remodeled)
10.0 out of 10, Exceptional, 15 reviews
"The view is to die for lots of places walk dogs. The house gave us everything we needed. It is very peaceful. Thank you"
The price is AU$312
per night
17 July - 18 July
Lake/Beach Getaway (Remodeled)
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See all available properties in Winthrop Harbor
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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2.5 star property
8.8 out of 10, Excellent, 1,000 reviews
"Nice staff and easy to navigate"
The price is AU$173
per night
23 June - 24 June
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Great Wolf Lodge Illinois
3.0 star property
8.6 out of 10, Excellent, 720 reviews
"Nice property, quick check ins"
The price is AU$315
per night
7 July - 8 July
Great Wolf Lodge Illinois
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.

Everything you need to know about Winthrop Harbor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop Harbor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winthrop Harbor holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winthrop Harbor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winthrop Harbor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winthrop Harbor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winthrop Harbor holiday rentals we have selected for you start as low as AU$164 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winthrop Harbor rentals

At Expedia, we put the best Winthrop Harbor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winthrop Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winthrop Harbor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winthrop Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Spring Bluff Forest Preserve are a couple of lovely local spots to get outside and enjoy nature. You’ll find favourite places to visit such as Six Flags Great America and Naval Base Great Lakes 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.

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