Winthrop Harbor Vacation Rentals

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Check prices for these dates

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Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Winthrop Harbor vacation rentals

Exterior
Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.

Vacation Home in Winthrop Harbor

Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
2.0 star property
The price is ￥19,258
￥41,153 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
Microwave, oven, stovetop, dishwasher
Home -2 bedroom, 4k projector

Vacation Home in Waukegan

Home -2 bedroom, 4k projector
2.0 star property
8.8 out of 10, Excellent, (3)
"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 ￥15,657
￥37,500 total
includes taxes & fees
Dec 30 - Dec 31
Home -2 bedroom, 4k projector
House (4 Bedrooms) | Interior
Salem Vacation Home w/ Dock: Steps to Paddock Lake

Cottage in Salem

Salem Vacation Home w/ Dock: Steps to Paddock Lake
3.0 star property
The price is ￥16,127
￥101,948 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Property grounds
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Vacation Home in Kenosha

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
9.6 out of 10, Exceptional, (87)
"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 ￥10,177
￥17,238 total
includes taxes & fees
Dec 30 - Dec 31
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Bar (on property)
Randolph Hotel Capone Suite 201

Apartment in Fox Lake

Randolph Hotel Capone Suite 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. "
United States
Daniel H.
The price is ￥17,614
￥79,071 total
includes taxes & fees
Dec 30 - Dec 31
Randolph Hotel Capone Suite 201
Smart TV
Charming 2-bedroom house with a pier and kayaks in Paddock Lake

Vacation Home in Salem

Charming 2-bedroom house with a pier and kayaks in Paddock Lake
10.0 out of 10, Exceptional, (10)
"Excellent property and location!"
United States
Rod L.
The price is ￥19,571
￥35,020 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming 2-bedroom house with a pier and kayaks in Paddock Lake
Fridge, microwave, oven, stovetop
Newly remodeled-Near Lake 4BR w/ Hot Tub & Games

Vacation Home in Gages Lake

Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
2.0 star property
10.0 out of 10, Exceptional, (1)
"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 ￥36,168
￥105,563 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
Beach nearby
Beach Lake Michigan King Bed Pet Friendly

Villa in Downtown Kenosha

Beach Lake Michigan King Bed Pet Friendly
9.0 out of 10, Wonderful, (16)
"This is a lovely place to stay…it’s cozy, well-stocked and located right near the beach (Lake Michigan). We had a wonderful week here! "
United States
Robert D.
The price is ￥20,104
￥44,216 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beach Lake Michigan King Bed Pet Friendly
Terrace/patio
Manor creek Vacation Getaway-Navy-PrivateYard-Game

Vacation Home in Beach Park

Manor creek Vacation Getaway-Navy-PrivateYard-Game
2.0 star property
10.0 out of 10, Exceptional, (1)
"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 ￥34,759
￥104,956 total
includes taxes & fees
Dec 30 - Dec 31
Manor creek Vacation Getaway-Navy-PrivateYard-Game
Microwave, oven, stovetop
Cute & Cozy, 1bd Condo Apartment/townhouse

Condo in Zion

Cute & Cozy, 1bd Condo Apartment/townhouse
10.0 out of 10, Exceptional, (2)
"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 ￥15,500
￥37,334 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cute & Cozy, 1bd Condo Apartment/townhouse
Dining
Quaint Bungalow, near Great Lakes Naval Base

Vacation Home in Mundelein

Quaint Bungalow, near Great Lakes Naval Base
9.8 out of 10, Exceptional, (68)
"Great place and great price. Lots of restaurants around. Minutes from the highway for city access."
United States
Joseph B.
The price is ￥21,137
￥51,937 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Quaint Bungalow, near Great Lakes Naval Base
Exterior
Wisconsin Treehouse Getaway!

Apartment in Racine

Wisconsin Treehouse Getaway!
9.6 out of 10, Exceptional, (26)
"We had a wonderful time staying here while visiting the surrounding area!"
United States
Collin C.
The price is ￥19,728
￥38,386 total
includes taxes & fees
Dec 30 - Dec 31
Wisconsin Treehouse Getaway!
Outdoor dining
Hot Tub Retreats

Vacation Home in Lake Villa

Hot Tub Retreats
2.0 star property
The price is ￥24,926
￥37,201 total
includes taxes & fees
Dec 30 - Dec 31
Hot Tub Retreats
Fridge, microwave, oven, stovetop
North Chi retreatNavySaunaTiki BarGames

Vacation Home in North Chicago

North Chi retreatNavySaunaTiki BarGames
10.0 out of 10, Exceptional, (15)
"Perfect location so close to Great Lakes Naval Base! We couldn’t have asked for a better location. The house was lovely and had many thoughtful amenities. We would definitely stay again. "
United States
nancy f.
The price is ￥34,602
￥99,807 total
includes taxes & fees
Jan 4 - Jan 5, 2026
North Chi retreatNavySaunaTiki BarGames
Exterior
This is a VACATION spot with a million dollar view!

Vacation Home in fox lake

This is a VACATION spot with a million dollar view!
9.8 out of 10, Exceptional, (19)
"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 ￥17,614
￥39,740 total
includes taxes & fees
Jan 1 - Jan 2, 2026
This is a VACATION spot with a million dollar view!
Fridge, microwave, oven, stovetop
Apartment Attached to a 1900 historic Farm house

Apartment in Old Mill Creek

Apartment Attached to a 1900 historic Farm house
8.6 out of 10, Excellent, (17)
"If I had to choose a word, it would be thoughtful. From the extra toiletries and towels to the coffee selection and soft bedding, it was an enjoyable stay. It was also wonderful to feel like my doggo was not just allowed but welcomed. Bowls and bed provided, with a short trail cut for us to explore. "
United States
Mary M.
The price is ￥22,546
￥40,985 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Apartment Attached to a 1900 historic Farm house
Terrace/patio
3-bedroom vacation home just a short walk to Lake Michigan

Vacation Home in Racine

3-bedroom vacation home just a short walk to Lake Michigan
9.2 out of 10, Wonderful, (34)
"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 ￥21,137
￥41,583 total
includes taxes & fees
Jan 20 - Jan 21, 2026
3-bedroom vacation home just a short walk to Lake Michigan
Terrace/patio
Beautiful and Cozy With 5 Bedrooms

Vacation Home in Zion

Beautiful and Cozy With 5 Bedrooms
9.0 out of 10, Wonderful, (18)
"Everything was good"
United States
Jayden????
The price is ￥35,228
￥84,294 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beautiful and Cozy With 5 Bedrooms
Exterior
Greenbay Paradise-Huge outdoor-Trail-Game-Navy

Vacation Home in Beach Park

Greenbay Paradise-Huge outdoor-Trail-Game-Navy
2.0 star property
The price is ￥34,602
￥104,298 total
includes taxes & fees
Dec 30 - Dec 31
Greenbay Paradise-Huge outdoor-Trail-Game-Navy
Smart TV, fireplace, foosball, video library
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls

Vacation Home in Gurnee

Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
9.8 out of 10, Exceptional, (37)
"Perfect for 3 families with a couple of dogs."
United States
Hans Z.
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
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

The Inn on Sheridan

The Inn on Sheridan

10/10 Excellent
"All"
Tisha 2-night trip
Posted 3 days ago
The Inn on Sheridan

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:

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Frequently asked questions

Are there vacation rentals in Winthrop Harbor?

Yes, you can find vacation rentals close to the most popular sights in Winthrop Harbor, or you can select a secluded option if you're looking for relaxation. Winthrop Harbor is known for its beaches and restaurants.

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

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft: This vacation home rental outside of Winthrop Harbor is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a pool table, and a hot tub so you can immerse yourself in your vacation.

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 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.