Winthrop Harbor Holiday 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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Winthrop Harbor

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

10.0 out of 10, Exceptional, (1)
"Very nice and newly remodeled property. Would definitely recommend. Property owner was pleasant and attended to maintenance issues promptly. Pool table and air hockey tables were fun to play on. There is even a sauna on the property but we did not use it. Great location for being near the Naval base."
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (30)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Tiny Home Retreat with hot tub

6.0 out of 10, (1)
"Just the pictures looked more entertaining than it actually was. .. small but pretty dam cool . Huge yard but hot tub was on the other end of the yard which has a camera. Who want to be video wial in the hot tub ? But over all.. we were not bothered at all and they had candy in the room ready .. "
The price is AU$479
includes taxes & fees
13 Aug - 14 Aug
Tiny Home Retreat with hot tub

New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

10.0 out of 10, Exceptional, (2)
"We were there for a horse show and it was the perfect place after a long day at the show. "
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (13)
"We had a wonderful stay! The home was immaculate and had a great layout that made it easy for our family to relax and connect. The pictures do not to the home justice, it’s even nicer than it appears. Kelly was incredibly kind and responsive throughout our visit. We’d be happy to return the next time we’re in the area!"
The price is AU$608
includes taxes & fees
11 Aug - 12 Aug
Charming 3-bedroom house in Grayslake

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

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

10.0 out of 10, Exceptional, (82)
"Very nice home very cozy beautiful view"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

Marina Life II - 28 Carver @ Reef Point Marina

9.6 out of 10, Exceptional, (44)
"This is a super fun place to stay! The marina has excellent amenities and the boat was clean and well appointed."
The price is AU$376
includes taxes & fees
7 Aug - 8 Aug
Marina Life II - 28 Carver @ Reef Point Marina

Roxan Corner

8.6 out of 10, Excellent, (37)
"Close to our family and friends. "
Roxan Corner

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (17)
"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

9.8 out of 10, Exceptional, (34)
"The view was spectacular!"
Cute and Cozy Cottage by the Lake! Kayaks! Paddleboard! HUGE Deck w/ Great Views

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (47)
"Overall nice stay, the master shower didn’t work but there were 2 other bathrooms, "
Beautiful and spacious lakefront home! Close to everything!

The Randolph Hotel Apt 201

6.0 out of 10, (2)
"Staying in the Round Lake Beach area to visiting family. Room is great and clean. Pretty view of Fox Lake. Only draw back is it is over a bar. Karaoke comes right up through the floor. Not to much of a problem as the bar closes at 11:00. So just have to suffer through the drunken super star want a be singers. It is good for some laughs. Over all I would recommend this place in a heartbeat. "
The price is AU$505
includes taxes & fees
7 Aug - 8 Aug
The Randolph Hotel Apt 201

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

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.

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

Entire Beautiful Grove Home

9.0 out of 10, Wonderful, (11)
"The space of the house was great. Didnt use any of the big back yard. Had a lot of loud music the last two nights. Kept us awake . Even heard with earplugs."
Entire Beautiful Grove Home

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

9.6 out of 10, Exceptional, (28)
"The home had everything we needed. The host was very attentive to any needs that came up. Neighborhood was close to navy bootcamp graduation. The neighborhood was quiet and we felt very safe being there. Would recommend this home to families that are coming in!"
great home in Waukegan for navy graduate families close distance to navy base!!

Scenic Waterfront Lake Michigan Escape

10.0 out of 10, Exceptional, (12)
"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

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

9.0 out of 10, Wonderful, (12)
"Our family gathered to visit our Carthage (Kenosha) student and view a lacrosse game. There was plenty of space for all and the outdoor area was very nice for eating and relaxing. Loved that there were multiple refrigerators, huge islands in the kitchen and a grill. We rented both units and had plenty of space for 12 people."
Lakefront home with firepit, 2 kitchens, & 2 W/Ds
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

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.

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 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.