Winthrop Harbor Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

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.
10.0 out of 10, Exceptional, (3 reviews)
"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$665
HK$1,749 total
includes taxes & fees
3 Mar - 4 Mar
Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
Interior

Cottage in Salem

Salem Vacation Home w/ Dock: Steps to Paddock Lake
3.0 star property
The price is HK$806
HK$5,094 total
includes taxes & fees
8 Mar - 9 Mar
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Property grounds

Holiday Home in Kenosha

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
9.6 out of 10, Exceptional, (88 reviews)
"Beautiful neighborhood homes. The lake is very close with great views. Clean room and a comfortable bed."
United States
Lynette C.
The price is HK$509
HK$861 total
includes taxes & fees
7 Mar - 8 Mar
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Exterior detail

Holiday Home in Mundelein

Quaint Bungalow, near Great Lakes Naval Base
9.8 out of 10, Exceptional, (69 reviews)
"Really amazing place. Adorable house, plenty of space, conveniently located. Great linens on the beds & amenities in the bathroom. Owner was incredibly flexible and responsive and great to work here. Had three visitors from Europe and they absolutely loved the place and had a great time. Would 100% stay here again the next time we're in the area. "
United States
Erika H.
The price is HK$1,056
HK$2,595 total
includes taxes & fees
3 Mar - 4 Mar
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, (23 reviews)
"Host was very responsive and view of lake was beautiful. Always nice to have lots of space to enjoy time with grandkids and have meals together. "
United States
Wendie B.
The price is HK$978
HK$2,123 total
includes taxes & fees
3 Mar - 4 Mar
This is a VACATION spot with a million dollar view!
Fridge, microwave, oven, stovetop

Holiday Home in Gages Lake

Newly remodeled Near Lake 4BR Hot Tub Navy Family home
10.0 out of 10, Exceptional, (4 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
The price is HK$1,181
HK$5,948 total
includes taxes & fees
3 Mar - 4 Mar
Newly remodeled Near Lake 4BR Hot Tub Navy Family home
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$775
HK$1,882 total
includes taxes & fees
3 Mar - 4 Mar
Cute & Cozy, 1bd Condo Apartment/townhouse
Interior

Holiday Home in Zion

Beautiful and Cozy With 5 Bedrooms
9.0 out of 10, Wonderful, (20 reviews)
"Cool"
United States
??????? ?.
The price is HK$1,760
HK$4,237 total
includes taxes & fees
3 Mar - 4 Mar
Beautiful and Cozy With 5 Bedrooms
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$951
HK$1,967 total
includes taxes & fees
3 Mar - 4 Mar
3-bedroom vacation home just a short walk to Lake Michigan
Exterior

Apartment in Racine

Wisconsin Treehouse Getaway!
9.6 out of 10, Exceptional, (28 reviews)
"Such an amazing stay! Everything was clean, the hosts were so friendly and accommodating. The place is gorgeous; and quiet. Thank you for everything! "
United States
Danielle B.
The price is HK$986
HK$1,918 total
includes taxes & fees
3 Mar - 4 Mar
Wisconsin Treehouse Getaway!
Outdoor dining

Cabin in Lake Villa

Tiny Home Retreat with hot tub
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
The price is HK$1,244
HK$2,678 total
includes taxes & fees
3 Mar - 4 Mar
Tiny Home Retreat with hot tub
Outdoor dining

Holiday Home in Lake Villa

Hot Tub Retreats
The price is HK$1,557
HK$2,247 total
includes taxes & fees
3 Mar - 4 Mar
Hot Tub Retreats
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$939
HK$1,700 total
includes taxes & fees
3 Mar - 4 Mar
Charming 2-bedroom house with a pier and kayaks in Paddock Lake
Interior

Apartment in Old Mill Creek

Apartment Attached to a 1900 historic Farm house
8.6 out of 10, Excellent, (18 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$1,127
HK$2,065 total
includes taxes & fees
3 Mar - 4 Mar
Apartment Attached to a 1900 historic Farm house
Smart TV, offices

Holiday Home in North Chicago

North Chi retreatNavySaunaTiki BarGames
10.0 out of 10, Exceptional, (22 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$1,510
HK$6,100 total
includes taxes & fees
3 Mar - 4 Mar
North Chi retreatNavySaunaTiki BarGames
TV, fireplace

Holiday Home in North Chicago

Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
The price is HK$1,515
HK$3,214 total
includes taxes & fees
10 Mar - 11 Mar
Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base
Microwave, oven, stovetop, dishwasher

Holiday Home in Waukegan

Home -2 bedroom, 4k projector
9.0 out of 10, Wonderful, (4 reviews)
"Very nice stay, plenty of room with a garage and very quiet. Great location to the naval base recruit graduation. Owner was in constant contact and very helpful!!"
United States
Tim and kelsey J.
Home -2 bedroom, 4k projector
Dining

Holiday Home in Beach Park

Greenbay Paradise-Navy 3 Mile Private Huge outdoor
The price is HK$1,549
HK$6,439 total
includes taxes & fees
8 Mar - 9 Mar
Greenbay Paradise-Navy 3 Mile Private Huge outdoor
Smart TV, fireplace, books, music library

Holiday Home in Racine

Mid-Century Modern Dream Getaway
9.8 out of 10, Exceptional, (13 reviews)
"Had a couple glitches but host helped fix right away…..it was just like being at home.We have stayed here before and will hopefully return next year!"
United States
Teresa Y.
The price is HK$2,151
HK$4,292 total
includes taxes & fees
28 Mar - 29 Mar
Mid-Century Modern Dream Getaway
TV, fireplace, table football, offices

Holiday Home in Beach Park

Manor creek Vacation Getaway-Navy-PrivateYard-Game
10.0 out of 10, Exceptional, (3 reviews)
"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$1,549
HK$6,439 total
includes taxes & fees
8 Mar - 9 Mar
Manor creek Vacation Getaway-Navy-PrivateYard-Game
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

Days Inn by Wyndham Waukegan

Days Inn by Wyndham Waukegan

10/10 Excellent
"It was really nice "
Kristina 5-night trip
Posted 3 days ago
Days Inn by Wyndham Waukegan

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?

Large Group Retreat w/ secluded party room and private pool: This holiday home rental outside of Winthrop Harbor offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with an arcade/games room and 1 hot tub.

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.