Winthrop Harbor Vacation Rentals from $242: Search Short-Term Rentals

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Our top choices for Winthrop Harbor vacation rentals

A living room with a sofa, coffee table, lamp, and a staircase.

1. Cute & Cozy, 1bd Condo Apartment/townhouse

Zion

Tristan P.

$244 nightly

Sep 15 - Sep 16

Total with taxes and fees

A modern living room with a flat-screen TV, a coffee table, a blue armchair, and a gray sofa.

2. The Beach Park Retreat

Beach Park

$233 nightly

Sep 8 - Sep 9

Total with taxes and fees

A living room with a sectional sofa, a patterned armchair, a coffee table, and a lamp.

3. The Rooftop - Haven!

Waukegan

$244 nightly

Sep 6 - Sep 7

Total with taxes and fees

A modern living room with a grey sofa, a blue armchair, and a dining area with a table and chairs.

4. Greenwood Loft & Rooftop

Waukegan

$236 nightly

Sep 15 - Sep 16

Total with taxes and fees

A kitchen with wooden cabinets, a black countertop, and a window.

5. Beautiful and Cozy With 5 Bedrooms

Zion

randy w.

$714 nightly

Sep 8 - Sep 9

Total with taxes and fees

A living room with a television on a stand, a potted plant, a glass coffee table, and a window with curtains.

6. Apartment Attached to a 1900 historic Farm house

Old Mill Creek

Matt H.

$227 nightly

Sep 8 - Sep 9

Total with taxes and fees

A compact RV bedroom with a bed, a small dresser, and a kitchenette.

7. Spacious 27’ RV on horse farm

Bristol

Faith N.

$110 nightly

Sep 8 - Sep 9

Total with taxes and fees

A two-story house with a stone chimney, a front porch with steps, and a flag.

8. Quaint Bungalow, near Great Lakes Naval Base

Mundelein

Jaclyn Z.

$333 nightly

Sep 8 - Sep 9

Total with taxes and fees

9. Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

North Chicago

"Rented this property for my sons navy graduation, Base was only 6 minutes from the home. Tons of places to eat and shop no more then 15 minutes away. The house was super cute, very clean. we flew in at 10am and without even having to ask the host reached out and let us know it was ready for check in a few hours early which was great. left some packaged up congrats grad decor that hopefully didnt get thrown out and the next navy fam can use. "

Linda U.

$555 nightly

Sep 8 - Sep 9

Total with taxes and fees

A group of people seated around a round table with a fire pit in the center, overlooking a marina with boats and a cityscape in the background.

10. Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19

Racine

Carrie

$211 nightly

Sep 8 - Sep 9

Total with taxes and fees

A dining area with a wooden table, chairs, a clock, and a pendant light.

11. Great America Getaway | Sleeps 12 | Near Navy Base

Gurnee

$689 nightly

Sep 12 - Sep 13

Total with taxes and fees

A small kitchenette area with a coffee maker, a toaster, a bottle of champagne, and a sign that reads "Welcome Mr. Cong."

12. Irish Mist V @ Reefpoint Marina

Racine

Joseph P.

$240 nightly

Sep 7 - Sep 8

Total with taxes and fees

A spacious living room with a wooden floor, a dining area, and a kitchen in the background.

13. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem

Shanna D.

$872 nightly

Sep 4 - Sep 5

Total with taxes and fees

A swimming pool with a curved edge and a single visible lane.

14. Marina Life II - 28 Carver @ Reef Point Marina

Racine

Douglas E.

$229 nightly

Sep 7 - Sep 8

Total with taxes and fees

An outdoor patio with a hot tub, wicker chairs, and a table.

15. Hot Tub Retreats

Lake Villa

Rosilynn B.

$314 nightly

Sep 7 - Sep 8

Total with taxes and fees

A modern living space with a kitchen, dining area, and a cozy seating area.

16. Charming 2-bedroom Channel house and kayaks in Paddock Lake

Salem

Rod L.

$239 nightly

Oct 1 - Oct 2

Total with taxes and fees

A glass-enclosed gazebo with a metal roof, wooden deck, and a statue of a person.

17. Wisconsin Treehouse Getaway!

Racine

Stephanie

$219 nightly

Sep 8 - Sep 9

Total with taxes and fees

18. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem

$852 nightly

Sep 4 - Sep 5

Total with taxes and fees

A hotel room with a bed, two bedside lamps, a chair, a nightstand, a framed picture on the wall, and a window with a view.

19. Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Chicago

Anonymous traveler

$91 nightly

Sep 30 - Oct 1

Total with taxes and fees

20. Tiny Home Retreat with hot tub

Lake Villa

Aaron L.

$399 nightly

Sep 6 - Sep 7

Total with taxes and fees

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Top Winthrop Harbor Hotel Reviews

Comfort Suites Grayslake near Libertyville North

10/10 Excellent

"I could use a little bit of cleaning on the couches. But overall, the staff and the place is great for the price."

Days Inn by Wyndham Great Lakes Naval Base

10/10 Excellent

"Room was clean, staff was very helpful. Breakfast tasted good but would have loved some meat and protein like sausage and eggs. Parking was plentiful and there was a handicapped spot easily accessible for us to load and unload our things. We definitely would stay here again. Thank you."

Motel Sun Inn

8/10 Good

"As 2 women traveling, we were a bit hesitant after seeing the lobby. The check-in counter is behind plexiglass, and the decor is pretty dated. There are smoking rooms in the hotel so there is a smell throughout. However we were content with our room. It was clean enough and quiet. The air conditioner was old but worked. Honestly, no complaints. It was located conveniently for our event. We got what we paid for in a totally acceptable way 🙂"

Illinois Beach Hotel

8/10 Good

"This property has so much potential because of its location and proximity to the beach, but it was unfortunately sad and deflated when we went. The best part of the property was the staff, who were polite and gracious. The room was also clean, but they have a pretty archaic temperature regulating system. I think at one time the property might have been a magnificent resort, but it was obvious that its prime was long past gone when we visited. There appeared to be some remodeling in progress, so I hope the redesign vamps it up and brings it life again. The restaurant food was cafeteria-ish too, which made me all the more sad because I could tell they were trying their best to give the illusion of high-end standards on a budget. To be fair, the weather was rainy, so maybe the gloom impacted the ambiance. I'm not opposed to coming back after the remodeling is done. I'm curious to see if my subpar experience was just due to the circumstances at the time."

Find out more about Winthrop Harbor

Everything you need to know about Winthrop Harbor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop Harbor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winthrop Harbor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop Harbor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winthrop Harbor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winthrop Harbor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $242 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop Harbor rentals

At Expedia, we put the best Winthrop Harbor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winthrop Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winthrop Harbor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winthrop Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Winthrop Harbor?

Yes, you can find vacation rentals where you'll be just 9.5 mi (15.3 km) from Six Flags Great America, giving you a secluded option to escape the hustle and bustle. 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 Spring Bluff Forest Preserve are a couple of lovely local spots to get outside and enjoy nature. While here, North Point Marina Beach and Winthrop Harbor Village Hall 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.

Winthrop Harbor Vacation Rentals

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Check prices for these dates

Our top choices for Winthrop Harbor vacation rentals

1. Cute & Cozy, 1bd Condo Apartment/townhouse

2. The Beach Park Retreat

3. The Rooftop - Haven!

4. Greenwood Loft & Rooftop

5. Beautiful and Cozy With 5 Bedrooms

6. Apartment Attached to a 1900 historic Farm house

7. Spacious 27’ RV on horse farm

8. Quaint Bungalow, near Great Lakes Naval Base

9. Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

10. Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19

11. Great America Getaway | Sleeps 12 | Near Navy Base

12. Irish Mist V @ Reefpoint Marina

13. Salem Vacation Home w/ Dock: Steps to Paddock Lake

14. Marina Life II - 28 Carver @ Reef Point Marina

15. Hot Tub Retreats

16. Charming 2-bedroom Channel house and kayaks in Paddock Lake

17. Wisconsin Treehouse Getaway!

18. Salem Vacation Home w/ Dock: Steps to Paddock Lake

19. Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

20. Tiny Home Retreat with hot tub

Find vacation rentals that suit your style

Top Winthrop Harbor Hotel Reviews

Comfort Suites Grayslake near Libertyville North

Find out more about Winthrop Harbor

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