Winthrop Harbor Vacation Rentals

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Vacation Rentals in Winthrop Harbor

Our top choices for Winthrop Harbor vacation rentals

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (16)
"Fells like home very cozy calm area definitely a get away relaxing place "
The price is CA $344
CA $663 total
includes taxes & fees
Sep 1 - Sep 2
Charming 3-bedroom house in Grayslake

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

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.

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

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (32)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

Entire 3 Bedroom Cozy Unit

9.6 out of 10, Exceptional, (21)
"This property was comfortable and convenient for our attendance at the Navy boot camp graduation. "
Entire 3 Bedroom Cozy Unit

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 CA $206
CA $332 total
includes taxes & fees
Sep 1 - Sep 2
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

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!!

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!

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

This is a VACATION spot with a million dollar view!

9.8 out of 10, Exceptional, (14)
"Comfortable and pleasant view of the lake"
The price is CA $216
CA $423 total
includes taxes & fees
Sep 1 - Sep 2
This is a VACATION spot with a million dollar view!

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 CA $124
CA $159 total
includes taxes & fees
Sep 1 - Sep 2
Spacious 27’ RV on horse farm

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (21)
"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

Tiny Home Retreat with hot tub

8.0 out of 10, Very good, (2)
"We had the most wonderful time"
The price is CA $177
CA $418 total
includes taxes & fees
Sep 1 - Sep 2
Tiny Home Retreat with hot tub

3-bedroom vacation home just a short walk to Lake Michigan

9.4 out of 10, Exceptional, (27)
"Great location close to the water cute house clean comfortable. Host was very accommodating to my allergy. Needs really enjoyed our stay highly recommend."
The price is CA $172
CA $357 total
includes taxes & fees
Sep 8 - Sep 9
3-bedroom vacation home just a short walk to Lake Michigan

A Diamond in the Rough

9.4 out of 10, Exceptional, (90)
"I will be staying here again in the future. Great place at a great location."
A Diamond in the Rough
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

Find out more about Winthrop Harbor

Everything you need to know about Winthrop Harbor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop Harbor vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winthrop Harbor vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winthrop Harbor vacation rentals we have selected for you start as low as CA $124 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 vacation 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 vacation.

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 vacation rentals in Winthrop Harbor?

Yes, you can find vacation rentals where you'll be just 9.5 mi (15.3 km) from Six Flags Great America, giving you a secluded option to escape the hustle and bustle. Winthrop Harbor is known for its beaches and restaurants.

What are some of the best vacation rentals in Winthrop Harbor?

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar: This vacation home rental outside of Winthrop Harbor offers a fireplace, a garden, and a barbecue grill 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 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 favorite places to visit like Naval Base Great Lakes and Six Flags Great America in the larger area.

What’s a vacation rental in Winthrop Harbor like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Winthrop Harbor. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.