Winthrop Harbor Vacation Rentals

    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
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jun 24 - Jun 25
Tomorrow
Jun 25 - Jun 26
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Winthrop Harbor

Charming 3-bedroom apartment with AC and WiFi in Waukegan.
Fridge, microwave, oven, stovetop

Charming 3-bedroom apartment with AC and WiFi in Waukegan.

9.6 out of 10, Exceptional, (5)
The price is ￥25,534
￥51,287 total
includes taxes & fees
Jun 30 - Jul 1
Charming 3-bedroom apartment with AC and WiFi in Waukegan.
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Smart TV, stereo

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

9.0 out of 10, Wonderful, (30)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.8 out of 10, Excellent, (27)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Scenic Waterfront Lake Michigan Escape
Property grounds

Scenic Waterfront Lake Michigan Escape

10.0 out of 10, Exceptional, (5)
"A small group of friends and I celebrated a birthday for a weekend here, and we loved it! The house is beautifully decorated (great for pictures) and had everything we needed. We loved the record player and backyard space. Thanks Daniel for the great stay!"
Scenic Waterfront Lake Michigan Escape
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Dining

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (78)
"We stayed here while skiing in Wilmot. Easy drive there and back. Plenty of room upstairs and down stairs to hang out. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Large Group Retreat w/ secluded party room and private pool
Fridge, microwave, oven, stovetop

Large Group Retreat w/ secluded party room and private pool

8.4 out of 10, Very Good, (16)
"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
Corporate Housing by MGM
Fridge, microwave, oven, stovetop

Corporate Housing by MGM

8.8 out of 10, Excellent, (9)
"We stayed here for a week for our sons Navy Graduation, 2/20/25...It was 12 mins from base, convenient, and although some reviews have that it was a little noisey, it was actually very quiet for us..quiet when we went."
The price is ￥25,231
￥44,661 total
includes taxes & fees
Jun 30 - Jul 1
Corporate Housing by MGM
Beautiful Huge Lakefront Remodeled Home with Incredible Views
Outdoor dining

Beautiful Huge Lakefront Remodeled Home with Incredible Views

9.8 out of 10, Exceptional, (27)
"This rental was excellent for our family vacation. We enjoyed beautiful views of the lake and sunset, meals on back deck and time spent on the lake. The owners is easy to communicate with and made us feel very welcomed. We would love to stay here again!"
Beautiful Huge Lakefront Remodeled Home with Incredible Views
Beautiful and spacious lakefront home! Close to everything!
Exterior detail

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (46)
"This property is beautiful!!! Very spacious and plenty of room for all of us. The bedrooms are all great sizes with room for pack n plays. Beautiful view of the lake! The kitchen was very stocked with plenty of dishes and cookware and your basic cooking needs. "
Beautiful and spacious lakefront home! Close to everything!
Chic Oasis/Game Room/Near Base/5 Bedroom
Fridge, microwave, oven, stovetop

Chic Oasis/Game Room/Near Base/5 Bedroom

2.0 star property
10.0 out of 10, Exceptional, (3)
"This was a great experience. Marta was great to work with and responded quickly to my questions before and during the stay. The house was clean and had everything we needed for our stay. The kids enjoyed the games and separate space in the basement. "
Chic Oasis/Game Room/Near Base/5 Bedroom
Chain O Lakes Lake Front Channel Lake
Fridge, microwave, oven, stovetop

Chain O Lakes Lake Front Channel Lake

10.0 out of 10, Exceptional, (7)
"Enjoyed peaceful time on the lake, house was clean and comfortable. Close to all kinds of food and places we liked to go. Would recommend."
Chain O Lakes Lake Front Channel Lake
Enjoy Lakefront living with family!
On the beach, beach towels

Enjoy Lakefront living with family!

9.8 out of 10, Exceptional, (68)
"Great location. Comfortable housing."
Enjoy Lakefront living with family!
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Marina

Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19

9.4 out of 10, Exceptional, (6)
"The boat was super clean, the bed was comfy, the host was communicative, and all the instructions were clear. We enjoyed the onsite hot tub and restaurant, and there’s plenty to do within walking distance as well."
The price is ￥19,698
￥32,481 total
includes taxes & fees
Jun 26 - Jun 27
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Entire Beautiful Grove Home
Smart TV, fireplace

Entire Beautiful Grove Home

9.0 out of 10, Wonderful, (10)
"It was an absolute delight. It is a beautiful home. Wonderful for Navy bootcamp famlies at graduation, 3 minutes from base!"
Entire Beautiful Grove Home
Wisconsin Treehouse Getaway!
Exterior

Wisconsin Treehouse Getaway!

9.8 out of 10, Exceptional, (21)
"Had a great time very relaxing with the creek there"
The price is ￥19,041
￥36,686 total
includes taxes & fees
Jul 7 - Jul 8
Wisconsin Treehouse Getaway!
Cozy second floor deplex 2-bedroom in peaceful Kenosha with AC, heat and WiFi
Interior

Cozy second floor deplex 2-bedroom in peaceful Kenosha with AC, heat and WiFi

2.0 star property
9.6 out of 10, Exceptional, (5)
"Caleb and family were so welcoming and easy to get a hold of if needed. Location was great for Kenosha and Pleasant Prairie. The apartment was perfect size and with all basic amenities needed. Thanks for a great stay! "
Cozy second floor deplex 2-bedroom in peaceful Kenosha with AC, heat and WiFi
Entire 3 Bedroom Cozy Unit
Smart TV, books

Entire 3 Bedroom Cozy Unit

9.4 out of 10, Exceptional, (15)
"First of all the place looked just like the pictures which we so appreciate! The property was very clean and had everything you would need! Location was very nice and felt like a very safe neighborhood. I would definitely stay there again as it checked all the boxes. Also, I really appreciated how quickly Karla got back to me every time I had a question. Thanks for a great stay....cheers!"
Entire 3 Bedroom Cozy Unit
Charming 3-bedroom house in Grayslake
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (10)
Charming 3-bedroom house in Grayslake
New Your Home Away From Home! - Near Great Lakes Naval Base!!
TV

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.2 out of 10, Wonderful, (25)
"Great stay for our Navy Sailor’s graduation, minutes away from the base."
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Near Lake 4BR w/ Hot Tub & Games | LCP Collection
Fridge, microwave, oven, stovetop

Near Lake 4BR w/ Hot Tub & Games | LCP Collection

10.0 out of 10, Exceptional, (10)
"This house had everything we needed and could have wanted! We had a wonderful stay. "
The price is ￥52,819
￥103,963 total
includes taxes & fees
Jul 22 - Jul 23
Near Lake 4BR w/ Hot Tub & Games | LCP Collection
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
Sign in
Sign up, it's free

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?

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families : This vacation home rental outside of Winthrop Harbor has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Winthrop Harbor?

With 3 Expedia vacation rentals, you're sure 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 favorite places to visit like Six Flags Great America and Naval Base Great Lakes 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.