Holiday Rentals in Winthrop Harbor

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Winthrop Harbor

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

9.6 out of 10, Exceptional, (4)
"Home was cute and as advertised, outdoor area great for families to relax. Only recommendation to have some information at the home for guests in the event the alarm system is activated so it can be acknowledged quickly. "
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (15)
"The house, yard and location were all perfect. "
The price is €454
includes taxes & fees
1 Sept - 2 Sept
Charming 3-bedroom house in Grayslake

Marina Life II - 28 Carver @ Reef Point Marina

9.6 out of 10, Exceptional, (45)
"We stayed for two nights at the house boat. The host communicated very efficiently and was nice. Even though the boat is small, it was cozy and we never felt cramped. We loved the amenities that are included in the marina. Walking distance from downtown so there was plenty to do. Would stay here again. "
The price is €212
includes taxes & fees
27 Aug - 28 Aug
Marina Life II - 28 Carver @ Reef Point Marina

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (30)
"Thank you very much"
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, (84)
"Was here for a funeral. Good place to stay and relaxing."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (48)
"Overall nice stay, the master shower didn’t work but there were 2 other bathrooms, "
Beautiful and spacious lakefront home! Close to everything!

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (241)
"What an incredible stay! The house was clean and organized. The open floor plan had lots of good spaces for family to gather. The views and property overall was beautiful! "
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Entire 3 Bedroom Cozy Unit

9.6 out of 10, Exceptional, (20)
"Just the right place for a quick trip with family! Great place if you are heading to Great Lakes for a Bootcamp graduation."
Entire 3 Bedroom Cozy Unit

Beautiful Spacious Escape On The Chain O'Lakes

9.2 out of 10, Wonderful, (61)
"Beautiful location, easy access. Could use carpet replaced, bed in large bedroom replaced. Otherwise we had a good stay."
Beautiful Spacious Escape On The Chain O'Lakes

A Diamond in the Rough

9.4 out of 10, Exceptional, (89)
"I will be staying here again in the future. Great place at a great location."
A Diamond in the Rough

Cozy RV in our land with community private beach, fire pit, bring your boat.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a nice time visiting Antioch, IL. The property clean, quiet and well maintained. The camper was adorable and very comfortable. Thank you!"
Cozy RV in our land with community private beach, fire pit, bring your boat.

Large Group Retreat w/ secluded party room and private pool

8.0 out of 10, Very good, (20)
"This property is better than advertised, it was exactly what we were hoping for. Pool area is awesome, all of the teenage boys LOVED the clubhouse, plenty of space to host. Communication with JJ was awesome. Would book again in a heartbeat and will have more stays there."
Large Group Retreat w/ secluded party room and private pool

Spacious 27’ RV on horse farm

8.6 out of 10, Excellent, (7)
"My stay here was great and I had everything I needed to be comfortable and enjoy myself. I was given a quick tour of the camper and shown how everything works, which was very helpful. I even got shown around the farm and really enjoyed seeing all of the beautiful horses and cute chickens."
The price is €103
includes taxes & fees
27 Aug - 28 Aug
Spacious 27’ RV on horse farm

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (20)
"Great little place to stay near the base. "
Family frndly TwnHm by navy base

Cute and Cozy Cottage by the Lake! Kayaks! Paddleboard! HUGE Deck w/ Great Views

10.0 out of 10, Exceptional, (35)
"The view was spectacular!"
Cute and Cozy Cottage by the Lake! Kayaks! Paddleboard! HUGE Deck w/ Great Views

Lakefront home with firepit, 2 kitchens, & 2 W/Ds

9.2 out of 10, Wonderful, (14)
"This property was perfect for a large group of people! Plenty of space for everyone to spread out and sleep comfortably. Overall we had a great experience at this property! "
Lakefront home with firepit, 2 kitchens, & 2 W/Ds

great home in Waukegan for navy graduate families close distance to navy base!!

9.6 out of 10, Exceptional, (28)
"Great place and very convenient to base"
great home in Waukegan for navy graduate families close distance to navy base!!

Beach Lake Michigan King Bed Pet Friendly

9.0 out of 10, Wonderful, (7)
"Judy's townhouse was a perfect spot for us to visit our family in Kenosha. We were all able to gather here to visit and enjoy the beautiful lakefront setting! "
Beach Lake Michigan King Bed Pet Friendly

Tiny Home Retreat with hot tub

8.0 out of 10, Very good, (2)
"We had the most wonderful time"
The price is €266
includes taxes & fees
27 Aug - 28 Aug
Tiny Home Retreat with hot tub

3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

9.2 out of 10, Wonderful, (11)
"Very happy with this stay. Clean and everything was as described. Bed was comfy. I would definatly recommend and stay again if needed. "
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winthrop Harbor Hotel Reviews

Find out more about Winthrop Harbor

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, 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 €103 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?

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar: This holiday home rental outside of Winthrop Harbor offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

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.