Winthrop Harbor Holiday Rentals

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Check prices for these dates

Tonight
14 Jan - 15 Jan
Tomorrow
15 Jan - 16 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Winthrop Harbor holiday rentals

Living area

Holiday Home in Winthrop Harbor

Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"This was everything in the description and more! Pet friendly, clean, quiet, spacious, and well-stocked! Our only regret was not being able to enjoy the nice yard and firepit because of the frigid temperatures. Our host was responsive friendly, and helpful. Excellent experience all the way around!"
United States
David B.
The price is HK$975
HK$2,050 total
includes taxes & fees
19 Jan - 20 Jan
Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
Property grounds

Holiday Home in Kenosha

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
9.6 out of 10, Exceptional, (87 reviews)
"Our room was perfect for our weekend visit with friends who lived nearby. The room had everything we needed and was very close to the lake, which has a lovely walking path. Our hosts were kind and helpful."
United States
Julia H.
The price is HK$507
HK$859 total
includes taxes & fees
15 Jan - 16 Jan
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Fridge, microwave, oven, stovetop

Holiday Home in Gages Lake

Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
United States
Danielle S.
The price is HK$858
HK$4,140 total
includes taxes & fees
18 Jan - 19 Jan
Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
Microwave, oven, stovetop, dishwasher

Holiday Home in Waukegan

Home -2 bedroom, 4k projector
2.0 star property
8.8 out of 10, Excellent, (3 reviews)
"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "
United States
You Tha Truth B.
The price is HK$975
HK$2,100 total
includes taxes & fees
16 Jan - 17 Jan
Home -2 bedroom, 4k projector
Interior

Cottage in Salem

Salem Vacation Home w/ Dock: Steps to Paddock Lake
3.0 star property
The price is HK$803
HK$5,077 total
includes taxes & fees
25 Jan - 26 Jan
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Smart TV

Holiday Home in Salem

Charming 2-bedroom house with a pier and kayaks in Paddock Lake
10.0 out of 10, Exceptional, (11 reviews)
"Excellent property and location!"
United States
Rod L.
The price is HK$858
HK$1,588 total
includes taxes & fees
20 Jan - 21 Jan
Charming 2-bedroom house with a pier and kayaks in Paddock Lake
Smart TV, offices

Holiday Home in North Chicago

North Chi retreatNavySaunaTiki BarGames
9.8 out of 10, Exceptional, (18 reviews)
"Nice clean home, easy check in processes close to the base. Perfect for our stay with kids. "
United States
Thomas D.
The price is HK$975
HK$4,052 total
includes taxes & fees
19 Jan - 20 Jan
North Chi retreatNavySaunaTiki BarGames
Smart TV

Condo in Zion

Cute & Cozy, 1bd Condo Apartment/townhouse
10.0 out of 10, Exceptional, (2 reviews)
"The property was very clean and has a very relaxing feel to it. The owner was very responsive when I had any questions and was very helpful. "
United States
Caleb C.
The price is HK$772
HK$1,860 total
includes taxes & fees
28 Jan - 29 Jan
Cute & Cozy, 1bd Condo Apartment/townhouse
Beach nearby

Villa in Downtown Kenosha

Beach Lake Michigan King Bed Pet Friendly
9.0 out of 10, Wonderful, (16 reviews)
"The place was nice and in a great location."
United States
Wyatt K.
The price is HK$1,030
HK$2,242 total
includes taxes & fees
15 Jan - 16 Jan
Beach Lake Michigan King Bed Pet Friendly
Exterior detail

Holiday Home in Mundelein

Quaint Bungalow, near Great Lakes Naval Base
9.8 out of 10, Exceptional, (68 reviews)
"Super cozy!! The neighborhood is so so so lovely! "
United States
Andrea M.
The price is HK$1,053
HK$2,563 total
includes taxes & fees
18 Jan - 19 Jan
Quaint Bungalow, near Great Lakes Naval Base
Marina

Holiday Home in fox lake

This is a VACATION spot with a million dollar view!
9.8 out of 10, Exceptional, (21 reviews)
"So easy to get to, right in the water. Has a dock for your boat. Sonja is very welcoming. "
United States
Kristina H.
The price is HK$975
HK$2,100 total
includes taxes & fees
18 Jan - 19 Jan
This is a VACATION spot with a million dollar view!
Marina

Apartment in Fox Lake

Randolph Hotel Capone Suite 201
6.0 out of 10, (2 reviews)
"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. "
United States
Daniel H.
The price is HK$878
HK$3,940 total
includes taxes & fees
15 Jan - 16 Jan
Randolph Hotel Capone Suite 201
Exterior

Apartment in Racine

Wisconsin Treehouse Getaway!
9.6 out of 10, Exceptional, (27 reviews)
"We had a wonderful time staying here while visiting the surrounding area!"
United States
Collin C.
The price is HK$983
HK$1,913 total
includes taxes & fees
19 Jan - 20 Jan
Wisconsin Treehouse Getaway!
Outdoor dining

Holiday Home in Racine

3-bedroom vacation home just a short walk to Lake Michigan
9.2 out of 10, Wonderful, (34 reviews)
"Great location near the beach, good kitchen, large fenced yard with lots of seating options, good communication with host"
United States
Donald N.
The price is HK$948
HK$1,961 total
includes taxes & fees
20 Jan - 21 Jan
3-bedroom vacation home just a short walk to Lake Michigan
TV, fireplace, table football, offices

Holiday Home in Beach Park

Manor creek Vacation Getaway-Navy-PrivateYard-Game
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"This is a wonderful space to enjoy time with family/friends. We hosted a birthday party and sleepover for young teens. The garage space was a perfect spot for a hangout. It was spacious for the sleepover and comfortable for everyone. It is close to modern conveniences. The host agency was super responsive!"
United States
Lisa Y.
The price is HK$1,623
HK$5,085 total
includes taxes & fees
18 Jan - 19 Jan
Manor creek Vacation Getaway-Navy-PrivateYard-Game
Interior

Holiday Home in Zion

Beautiful and Cozy With 5 Bedrooms
9.0 out of 10, Wonderful, (19 reviews)
"Everything was good"
United States
Jayden????
The price is HK$1,755
HK$4,200 total
includes taxes & fees
15 Jan - 16 Jan
Beautiful and Cozy With 5 Bedrooms
Outdoor dining

Holiday Home in Lake Villa

Hot Tub Retreats
2.0 star property
The price is HK$1,242
HK$1,812 total
includes taxes & fees
15 Jan - 16 Jan
Hot Tub Retreats
Interior

Apartment in Old Mill Creek

Apartment Attached to a 1900 historic Farm house
8.6 out of 10, Excellent, (17 reviews)
"It was really nice and the host very understanding when my dog got sick and messed in the house "
United States
Ceceilia R.
The price is HK$1,123
HK$2,042 total
includes taxes & fees
15 Jan - 16 Jan
Apartment Attached to a 1900 historic Farm house
WiFi, bed sheets

Holiday Home in North Chicago

Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
2.0 star property
The price is HK$1,498
HK$3,233 total
includes taxes & fees
15 Jan - 16 Jan
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
Smart TV, fireplace, books, music library

Holiday Home in Racine

Mid-Century Modern Dream Getaway
9.8 out of 10, Exceptional, (13 reviews)
"Overall very nice stay. Kids and family loved the backyard! "
United States
Jodie A.
The price is HK$1,759
HK$3,864 total
includes taxes & fees
30 Jan - 31 Jan
Mid-Century Modern Dream Getaway
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

Wingate by Wyndham Gurnee

Wingate by Wyndham Gurnee

10/10 Excellent
"Everything was just excellent "
Princess 2-night trip
Posted 9 hours ago
Wingate by Wyndham Gurnee

Find out more about Winthrop Harbor

Search for holiday rentals in Winthrop Harbor on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop Harbor using one of the methods below:

  • View our selection of featured holiday rentals in Winthrop Harbor
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Look no further and take a look at our great range of rental properties in Winthrop Harbor!

Frequently asked questions

Are there holiday rentals in Winthrop Harbor?

Yes, there are holiday rentals close to the most popular sights in Winthrop Harbor, or you can select a more secluded option if you're looking for a relaxing stay. Winthrop Harbor is known for its beaches and restaurants.

What are some of the best holiday rentals that Winthrop Harbor has to offer?

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft: This holiday home rental outside of Winthrop Harbor is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a pool table and 1 hot tub so that you can immerse yourself in your holiday.

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. While here, Winthrop Harbor Village Hall and North Point Marina are other places worth a visit.

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.