Winthrop Harbor Holiday Rentals

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Our top choices for Winthrop Harbor holiday rentals

The price is AU$344
includes taxes & fees
13 Jan - 14 Jan
Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
United States
Danielle S.
The price is AU$781
includes taxes & fees
13 Jan - 14 Jan
Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
9.6 out of 10, Exceptional, (87 reviews)
"Our room was perfect for our weekend visit with friends who lived nearby. The room had everything we needed and was very close to the lake, which has a lovely walking path. Our hosts were kind and helpful."
United States
Julia H.
The price is AU$168
includes taxes & fees
15 Jan - 16 Jan
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
The price is AU$974
includes taxes & fees
13 Jan - 14 Jan
Salem Vacation Home w/ Dock: Steps to Paddock Lake
9.8 out of 10, Exceptional, (68 reviews)
"Super cozy!! The neighborhood is so so so lovely! "
United States
Andrea M.
The price is AU$491
includes taxes & fees
13 Jan - 14 Jan
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (2 reviews)
"The property was very clean and has a very relaxing feel to it. The owner was very responsive when I had any questions and was very helpful. "
United States
Caleb C.
The price is AU$349
includes taxes & fees
13 Jan - 14 Jan
Cute & Cozy, 1bd Condo Apartment/townhouse
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"This is a wonderful space to enjoy time with family/friends. We hosted a birthday party and sleepover for young teens. The garage space was a perfect spot for a hangout. It was spacious for the sleepover and comfortable for everyone. It is close to modern conveniences. The host agency was super responsive!"
United States
Lisa Y.
The price is AU$789
includes taxes & fees
9 Feb - 10 Feb
Manor creek Vacation Getaway-Navy-PrivateYard-Game
9.0 out of 10, Wonderful, (16 reviews)
"Entire property clean, host very helpful and quick response time, family friendly, offered many extra amenities."
United States
Lesa S.
The price is AU$422
includes taxes & fees
14 Jan - 15 Jan
Beach Lake Michigan King Bed Pet Friendly

Apartment in Racine

Wisconsin Treehouse Getaway!
9.6 out of 10, Exceptional, (27 reviews)
"We had a wonderful time staying here while visiting the surrounding area!"
United States
Collin C.
The price is AU$369
includes taxes & fees
13 Jan - 14 Jan
Wisconsin Treehouse Getaway!
9.8 out of 10, Exceptional, (21 reviews)
"So easy to get to, right in the water. Has a dock for your boat. Sonja is very welcoming. "
United States
Kristina H.
The price is AU$402
includes taxes & fees
18 Jan - 19 Jan
This is a VACATION spot with a million dollar view!

Holiday Home in Waukegan

Home -2 bedroom, 4k projector
2.0 star property
8.8 out of 10, Excellent, (3 reviews)
"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "
United States
You Tha Truth B.
The price is AU$402
includes taxes & fees
13 Jan - 14 Jan
Home -2 bedroom, 4k projector
10.0 out of 10, Exceptional, (11 reviews)
"Excellent property and location!"
United States
Rod L.
The price is AU$305
includes taxes & fees
13 Jan - 14 Jan
Charming 2-bedroom house with a pier and kayaks in Paddock Lake
9.2 out of 10, Wonderful, (34 reviews)
"Great location near the beach, good kitchen, large fenced yard with lots of seating options, good communication with host"
United States
Donald N.
The price is AU$380
includes taxes & fees
20 Jan - 21 Jan
3-bedroom vacation home just a short walk to Lake Michigan
9.0 out of 10, Wonderful, (19 reviews)
"Everything was good"
United States
Jayden????
The price is AU$805
includes taxes & fees
13 Jan - 14 Jan
Beautiful and Cozy With 5 Bedrooms
8.8 out of 10, Excellent, (3 reviews)
"NICE PLACE, NICE NEIGHBORHOOD"
United States
stephen w.
The price is AU$507
includes taxes & fees
13 Jan - 14 Jan
Tiny Home Retreat with hot tub
8.6 out of 10, Excellent, (17 reviews)
"It was really nice and the host very understanding when my dog got sick and messed in the house "
United States
Ceceilia R.
The price is AU$390
includes taxes & fees
13 Jan - 14 Jan
Apartment Attached to a 1900 historic Farm house

Holiday Home in North Chicago

North Chi retreatNavySaunaTiki BarGames
9.8 out of 10, Exceptional, (18 reviews)
"Nice clean home, easy check in processes close to the base. Perfect for our stay with kids. "
United States
Thomas D.
The price is AU$764
includes taxes & fees
19 Jan - 20 Jan
North Chi retreatNavySaunaTiki BarGames

Holiday Home in Racine

Mid-Century Modern Dream Getaway
9.8 out of 10, Exceptional, (13 reviews)
"Overall very nice stay. Kids and family loved the backyard! "
United States
Jodie A.
The price is AU$720
includes taxes & fees
30 Jan - 31 Jan
Mid-Century Modern Dream Getaway

Holiday Home in Lake Villa

Hot Tub Retreats
2.0 star property
The price is AU$358
includes taxes & fees
13 Jan - 14 Jan
Hot Tub Retreats
2.0 star property
The price is AU$777
includes taxes & fees
13 Jan - 14 Jan
Greenbay Paradise-Huge outdoor-Trail-Game-Navy
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

Find out more about Winthrop Harbor

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$369 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, there are holiday rentals close to the most popular sights in Winthrop Harbor, or you can select a more secluded option if you're looking for a relaxing stay. Winthrop Harbor is known for its beaches and restaurants.

What are some of the best holiday rentals that Winthrop Harbor has to offer?

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft: This holiday home rental outside of Winthrop Harbor is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a pool table and 1 hot tub so that you can immerse yourself in your holiday.

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, Winthrop Harbor Village Hall and North Point Marina 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.