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Top Holiday Rentals in Winthrop Harbor

Private kitchen
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
6.8 out of 10, (3)
"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 £277
includes taxes & fees
5 Jun - 6 Jun
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
Property grounds
Unique and Charming Private Quarters
10.0 out of 10, Exceptional, (34)
"Sandy does a nice job of welcoming you, with her friendliness and her creative expression seen in every detail of her home. It was a very comfortable stay in all aspects. My one caution, which she has stated, is it is an upstairs apartment, so it is not handicap accessible in any way."
The price is £88
includes taxes & fees
4 Jun - 5 Jun
Unique and Charming Private Quarters
Property grounds
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, (40)
"Quaint and very clean."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
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Smart TV, stereo
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
"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 £190
includes taxes & fees
26 May - 27 May
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
TV
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.4 out of 10, Exceptional, (11)
"We really enjoyed the house, its very confortable, clean and the rooms are big. The house is very close to the base. Thanks."
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Property grounds
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
10.0 out of 10, Exceptional, (62)
"Beautiful, spectacular mornings with the sunrise and the view of the lake. The house is very comfortable. The kitchen is very nice. We were able to prepare all our family meals."
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
Private kitchen
Fully Updated home. Great for the entire family!
7.6 out of 10, Good, (10)
"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!
TV, books
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (46)
"Great location, floor plan, water pressure, all the things were well thought out and convenient. Will stay again."
The price is £252
includes taxes & fees
28 May - 29 May
Quaint Bungalow, near Great Lakes Naval Base
Terrace/patio
Roxan Corner
9.0 out of 10, Wonderful, (18)
"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
View from property
Beautiful and spacious lakefront home! Close to everything!
9.8 out of 10, Exceptional, (24)
"It was so much fun we had a great time!"
Beautiful and spacious lakefront home! Close to everything!
Property grounds
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
10.0 out of 10, Exceptional, (217)
"We had a great time! The house provided lots of space, loads of entertainment and opportunity for family fun. The weather was conducive for outdoor activities. All our needs and wants were met! We'll be back! Thank you!"
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Outdoor dining
SPACIOUS and Stylish Lakefront Retreat with VIEWS!
9.4 out of 10, Exceptional, (23)
"We booked this home for a long weekend for our book club. Honestly, we are all counting down the days until we have an excuse to do it again! The house is beautiful, well cared for and the hosts were super responsive. The layout is great for multiple couples, offering nice sized bedrooms and multiple full bathrooms. The fire pit on the water was a fan favorite as well, a perfect setting for sunset views. We can’t say enough about our experience and will definitely be returning yearly!"
SPACIOUS and Stylish Lakefront Retreat with VIEWS!
Property grounds
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes
9.6 out of 10, Exceptional, (50)
"This was a cute property and had an open and spacious feel inside. We really loved that all three rooms had a king sized bed and they were very comfortable! It was also a huge bonus that there was a second bathroom with a shower as we had to be somewhere fairly early on Saturday and everyone was able to get ready fast. The house also felt really solid and well insulated so each room felt like it had enough privacy. We would definitely stay here again!"
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes
Fridge, microwave, oven, stovetop
Pets are welcome! Outdoor BBQ Grill, Near Independence Grove Dog Park!
4.0 out of 10, (1)
"I left early to get another hotel."
The price is £103
includes taxes & fees
25 May - 26 May
Pets are welcome! Outdoor BBQ Grill, Near Independence Grove Dog Park!
Exterior
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
8.0 out of 10, Very good, (10)
"I've rented 26 homes in three years since I started using short term rentals. This is the worst I've ever had. Starting with check-in. NOT mentioned in the ad is the fact that you have to download a separate app to open the doors. This is a full-on registration...email/phone/etc. Shouldn't be needed and now I'm already getting fresh new spam! Yay! House rules: Don't use laundry room, it's unsafe. Oh but if you need to clean something, go ahead and use the laundry! OK, now the house. I WISH I...
The price is £196
includes taxes & fees
27 May - 28 May
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
Property grounds
The Beach Life!— Newly Renovated Beach Home awaits you!
10.0 out of 10, Exceptional, (14)
"Don’t be fooled by the modest exterior—the renovated interior of this house is charming and cozy. The owners have gone out of their way to provide the most comfortable bedrooms and fully equipped kitchen. There was autumn decor, new fleece blankets for snuggling, and 3 big TVs. Just a few hundred feet from a huge, clean beach, we also enjoyed the Racine Zoo, giant playground, board games, nearby haunted houses, and local eats. A friendly, diverse neighborhood great for a quiet but enjoyable...
The Beach Life!— Newly Renovated Beach Home awaits you!
Private kitchen
Modern Luxe home w/Gameroom and Electric Fireplace
8.4 out of 10, Very good, (6)
"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
Fridge, microwave, oven, stovetop
Serene Home! 6 Bed&4.5 Bath w/Kids den, Steam shower, Hot tub, Theatre, Bar..
10.0 out of 10, Exceptional, (1)
"This was a beautiful house with great service and response time. Thank you for making our board retreat special :)"
The price is £959
includes taxes & fees
27 May - 28 May
Serene Home! 6 Bed&4.5 Bath w/Kids den, Steam shower, Hot tub, Theatre, Bar..
Smart TV
5 min to Naval station Great Lake, Great lakes Commissary, RFU Medical School.
5 min to Naval station Great Lake, Great lakes Commissary, RFU Medical School.
Fridge, microwave, oven, stovetop
Lovely 4BR Lakeview House w/ Water Access
9.0 out of 10, Wonderful, (6)
"The house was really nice, we enjoyed our stay, enough space for 10-12 people, the only problem we had was the lighting outside of the house we didn’t have any light after sunset, we had to use our phone to us bbq grill."
Lovely 4BR Lakeview House w/ Water Access
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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.

Other types of properties in Winthrop Harbor you may be interested in

Indoor pool
La Quinta Inn & Suites by Wyndham Chicago Gurnee
2.5 star property
7.4 out of 10, Good, (1003)
"Stay was better than expected. Was met by what I think is the manager Turahn (spelling?) who did the best he could to allow an early check-in as my flight had arrived early for my granddaughter's HS Graduation. I got lost for an hour at the Cracker Barrel next door and came back and he assigned me a room. The room had recently been remodeled and was very updated. Staff is very friendly and do their best to please with a smile. I would recommend this as a comfortable, clean, safe placed to...
The price is £51
includes taxes & fees
28 May - 29 May
La Quinta Inn & Suites by Wyndham Chicago Gurnee
Exterior
Wingate by Wyndham Gurnee
2.5 star property
8.8 out of 10, Excellent, (1000)
"Enjoyed the stay."
The price is £73
includes taxes & fees
27 May - 28 May
Wingate by Wyndham Gurnee
Terrace/patio
Sonesta ES Suites Chicago Waukegan Gurnee
3.0 star property
8.8 out of 10, Excellent, (1004)
"Clean and quiet! Would definitely use this again. "
The price is £108
includes taxes & fees
17 Jun - 18 Jun
Sonesta ES Suites Chicago Waukegan 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.

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, apart-hotels, 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 favorite 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 depends 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 £88 per night. Entering your travel dates in the search wizard you might find 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?

Unique and Charming Private Quarters: This holiday home rental outside of Winthrop Harbor is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

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 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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