Winthrop Harbor Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

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 NZ$563
includes taxes & fees
17 May - 18 May
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 NZ$175
includes taxes & fees
22 May - 23 May
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, (39)
"Quaint and very clean."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$384
includes taxes & fees
19 May - 20 May
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
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
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.2 out of 10, Wonderful, (10)
"We were in North Chicago for PIR. It is less than 2 miles to the ceremony (we walked to avoid traffic and parking), there are ample rooms and beds for a family crew. Space to cook and serve and lounge about while your sailor decompresses. Restaurants are near enough (we got pizza from LouMalnatis in Gurnee), and grocery stores were close too. Communication was spot on, every time I had a question, they were on top of it (no issues, just questions)"
New Your Home Away From Home! - Near Great Lakes Naval Base!!
TV, books
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (45)
"This is one of the most charming vrbo that i have stayed at. the house is just as 1 described My son graduated Navy Bootcamp and it was so nice to have the comfort of this home vs sharing 3 hotel rooms."
The price is NZ$511
includes taxes & fees
20 May - 21 May
Quaint Bungalow, 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
Exterior
1929 charmer
The price is NZ$336
includes taxes & fees
19 May - 20 May
1929 charmer
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!
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
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
Luxury lake home with dock, patio, and deck!
10.0 out of 10, Exceptional, (23)
"Beautiful house. Clean"
Luxury lake home with dock, patio, and deck!
Property grounds
Lakefront Bliss: Your Ultimate Vacation Haven Surrounded by Nature
Lakefront Bliss: Your Ultimate Vacation Haven Surrounded by Nature
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 NZ$1,942
includes taxes & fees
23 May - 24 May
Serene Home! 6 Bed&4.5 Bath w/Kids den, Steam shower, Hot tub, Theatre, Bar..
Fridge, microwave, stovetop, coffee/tea maker
Salem Lakeside Getaway w/ Grill & Deck!
Salem Lakeside Getaway w/ Grill & Deck!
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
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
Property grounds
Lake/Beach Getaway (Remodeled)
10.0 out of 10, Exceptional, (15)
"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 NZ$333
includes taxes & fees
20 May - 21 May
Lake/Beach Getaway (Remodeled)
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!
Don't see what you're looking for?
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
7.2 out of 10, Good, (1002)
"Not bad at all"
The price is NZ$109
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, (999)
"Enjoyed the stay."
The price is NZ$154
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, (1002)
"We loved the space available in each room. It was clean and accessible to the Naval Base. The staff was friendly and accommodating. "
The price is NZ$189
includes taxes & fees
23 May - 24 May
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.

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.

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.

Recent reviews of Winthrop Harbor properties
Expedia verified reviews