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Top 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, (3)
"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

Marina Life II - 28 Carver @ Reef Point Marina

9.6 out of 10, Exceptional, (45)
"This is a super fun place to stay! The marina has excellent amenities and the boat was clean and well appointed."
The price is £183
includes taxes & fees
6 Sept - 7 Sept
Marina Life II - 28 Carver @ Reef Point Marina

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (15)
"The house, yard and location were all perfect. "
The price is £406
includes taxes & fees
25 Aug - 26 Aug
Charming 3-bedroom house in Grayslake

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.

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, (19)
"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

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

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

8.4 out of 10, Very good, (19)
"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

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (19)
"Great little place to stay near the base. "
Family frndly TwnHm by navy base

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 £89
includes taxes & fees
21 Aug - 22 Aug
Spacious 27’ RV on horse farm

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

Tiny Home Retreat with hot tub

8.0 out of 10, Very good, (2)
"We had the most wonderful time"
The price is £230
includes taxes & fees
24 Aug - 25 Aug
Tiny Home Retreat with hot tub

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

9.2 out of 10, Wonderful, (14)
"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

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

9.0 out of 10, Wonderful, (10)
"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

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

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 £261
includes taxes & fees
26 Aug - 27 Aug
The Randolph Hotel Apt 201

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (38)
"Nice and clean"
Lake/Beach Getaway (Remodeled)
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

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.