Winthrop Harbor Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Winthrop Harbor holiday rentals

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

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

Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
2.0 star property
Winthrop Harbor
Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
Fridge, microwave, oven, stovetop
Newly remodeled-Near Lake 4BR w/ Hot Tub & Games

Newly remodeled-Near Lake 4BR w/ Hot Tub & Games

Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
2.0 star property
Gages Lake
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$4,146 total
includes taxes & fees
19 Jan - 20 Jan
Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
Property grounds
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Kenosha
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$858 total
includes taxes & fees
15 Jan - 16 Jan
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Interior
Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem Vacation Home w/ Dock: Steps to Paddock Lake
3.0 star property
Salem
The price is HK$803
HK$5,077 total
includes taxes & fees
15 Jan - 16 Jan
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Exterior detail
Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
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$2,561 total
includes taxes & fees
18 Jan - 19 Jan
Quaint Bungalow, near Great Lakes Naval Base
Smart TV
Cute & Cozy, 1bd Condo Apartment/townhouse

Cute & Cozy, 1bd Condo Apartment/townhouse

Cute & Cozy, 1bd Condo Apartment/townhouse
Zion
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$733
HK$1,793 total
includes taxes & fees
15 Jan - 16 Jan
Cute & Cozy, 1bd Condo Apartment/townhouse
TV, fireplace, table football, offices
Manor creek Vacation Getaway-Navy-PrivateYard-Game

Manor creek Vacation Getaway-Navy-PrivateYard-Game

Manor creek Vacation Getaway-Navy-PrivateYard-Game
2.0 star property
Beach Park
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$1,622
HK$5,082 total
includes taxes & fees
18 Jan - 19 Jan
Manor creek Vacation Getaway-Navy-PrivateYard-Game
Beach nearby
Beach Lake Michigan King Bed Pet Friendly

Beach Lake Michigan King Bed Pet Friendly

Beach Lake Michigan King Bed Pet Friendly
Downtown Kenosha
9.0 out of 10, Wonderful, (16 reviews)
"The place was nice and in a great location."
United States
Wyatt K.
Beach Lake Michigan King Bed Pet Friendly
Exterior
Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
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$982
HK$1,911 total
includes taxes & fees
19 Jan - 20 Jan
Wisconsin Treehouse Getaway!
Marina
This is a VACATION spot with a million dollar view!

This is a VACATION spot with a million dollar view!

This is a VACATION spot with a million dollar view!
fox lake
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$2,099 total
includes taxes & fees
18 Jan - 19 Jan
This is a VACATION spot with a million dollar view!
Microwave, oven, stovetop, dishwasher
Home -2 bedroom, 4k projector

Home -2 bedroom, 4k projector

Home -2 bedroom, 4k projector
2.0 star property
Waukegan
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$2,099 total
includes taxes & fees
16 Jan - 17 Jan
Home -2 bedroom, 4k projector
Smart TV
Charming 2-bedroom house with a pier and kayaks in Paddock Lake

Charming 2-bedroom house with a pier and kayaks in Paddock Lake

Charming 2-bedroom house with a pier and kayaks in Paddock Lake
Salem
10.0 out of 10, Exceptional, (11 reviews)
"Excellent property and location!"
United States
Rod L.
The price is HK$858
HK$1,604 total
includes taxes & fees
15 Jan - 16 Jan
Charming 2-bedroom house with a pier and kayaks in Paddock Lake
Outdoor dining
3-bedroom vacation home just a short walk to Lake Michigan

3-bedroom vacation home just a short walk to Lake Michigan

3-bedroom vacation home just a short walk to Lake Michigan
Racine
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$947
HK$1,960 total
includes taxes & fees
20 Jan - 21 Jan
3-bedroom vacation home just a short walk to Lake Michigan
Interior
Beautiful and Cozy With 5 Bedrooms

Beautiful and Cozy With 5 Bedrooms

Beautiful and Cozy With 5 Bedrooms
Zion
9.0 out of 10, Wonderful, (19 reviews)
"Everything was good"
United States
Jayden????
The price is HK$1,754
HK$4,198 total
includes taxes & fees
15 Jan - 16 Jan
Beautiful and Cozy With 5 Bedrooms
Outdoor dining
Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub
Lake Villa
8.8 out of 10, Excellent, (3 reviews)
"NICE PLACE, NICE NEIGHBORHOOD"
United States
stephen w.
The price is HK$1,240
HK$2,652 total
includes taxes & fees
26 Jan - 27 Jan
Tiny Home Retreat with hot tub
Interior
Apartment Attached to a 1900 historic Farm house

Apartment Attached to a 1900 historic Farm house

Apartment Attached to a 1900 historic Farm house
Old Mill Creek
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$2,041 total
includes taxes & fees
22 Jan - 23 Jan
Apartment Attached to a 1900 historic Farm house
Smart TV, offices
North Chi retreatNavySaunaTiki BarGames

North Chi retreatNavySaunaTiki BarGames

North Chi retreatNavySaunaTiki BarGames
North Chicago
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$4,050 total
includes taxes & fees
19 Jan - 20 Jan
North Chi retreatNavySaunaTiki BarGames
Smart TV, fireplace, books, music library
Mid-Century Modern Dream Getaway

Mid-Century Modern Dream Getaway

Mid-Century Modern Dream Getaway
Racine
9.8 out of 10, Exceptional, (13 reviews)
"Overall very nice stay. Kids and family loved the backyard! "
United States
Jodie A.
Mid-Century Modern Dream Getaway
Outdoor dining
Hot Tub Retreats

Hot Tub Retreats

Hot Tub Retreats
2.0 star property
Lake Villa
The price is HK$1,241
HK$1,836 total
includes taxes & fees
19 Jan - 20 Jan
Hot Tub Retreats
Dining
Greenbay Paradise-Huge outdoor-Trail-Game-Navy

Greenbay Paradise-Huge outdoor-Trail-Game-Navy

Greenbay Paradise-Huge outdoor-Trail-Game-Navy
2.0 star property
Beach Park
The price is HK$826
HK$4,139 total
includes taxes & fees
25 Jan - 26 Jan
Greenbay Paradise-Huge outdoor-Trail-Game-Navy
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Harbor Hotel Reviews

Super 8 by Wyndham Sturtevant/Racine

Super 8 by Wyndham Sturtevant/Racine

10/10 Excellent
"Everything good."
Shonette 1-night trip
Posted 3 days ago
Super 8 by Wyndham Sturtevant/Racine

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
  • Use the map to find apartments and other holiday homes in the Winthrop Harbor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winthrop Harbor while they last

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.