Winthrop Harbor Vacation Rentals

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    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 24 - Oct 26
In one month
Nov 7 - Nov 9
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4

Vacation Rentals in Winthrop Harbor

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Dining

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (91)
"We throughly enjoyed our stay! The home was beautiful inside and the outside was nice being on the lake. I definitely would recommend this property to others!"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Family frndly TwnHm by navy base
Fridge, microwave, oven, stovetop

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (24)
"Great little place to stay near the base. "
Family frndly TwnHm by navy base
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (247)
"Beautiful view, wonderful house. Great morings with coffee on balcony!!"
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
great home in Waukegan for navy graduate families close distance to navy base!!
Fridge, microwave, oven, stovetop

great home in Waukegan for navy graduate families close distance to navy base!!

9.6 out of 10, Exceptional, (29)
"Great place and very convenient to base"
great home in Waukegan for navy graduate families close distance to navy base!!
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Fridge, microwave, oven, stovetop

3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

9.4 out of 10, Exceptional, (14)
"Very happy with this stay. Clean and everything was as described. Bed was comfy. I would definatly recommend and stay again if needed. "
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
North Chi retreat – Navy, Sauna, Tiki Bar, Games
Fridge, microwave, oven, stovetop

North Chi retreat – Navy, Sauna, Tiki Bar, Games

9.8 out of 10, Exceptional, (10)
North Chi retreat – Navy, Sauna, Tiki Bar, Games
This is a VACATION spot with a million dollar view!
Exterior

This is a VACATION spot with a million dollar view!

9.8 out of 10, Exceptional, (16)
"The house was beautiful and very close to my sisters house"
$577 nightly
The price is $612
Oct 7 - Oct 8
Total with taxes and fees
This is a VACATION spot with a million dollar view!
New Your Home Away From Home! - Near Great Lakes Naval Base!!
TV, fireplace

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.0 out of 10, Wonderful, (29)
"This was a great stay. Cute house with all the amenities . The neighborhood was quiet and close to everything. Definitely recommend for any families coming in for Navy graduations, the house is five minutes away from Great Lakes Navy base. "
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Roxan Corner
Fridge, microwave, oven, stovetop

Roxan Corner

8.6 out of 10, Excellent, (42)
"We enjoyed our stay! The neighborhood felt safe and we very much loved the space as they made it quite inviting with books and candles. I would have loved more blankets on the beds but overall we had a great stay!"
Roxan Corner
Lake/Beach Getaway (Remodeled)
Children's area

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (41)
"Perfect for what we needed. Right across from the lake, theres a cool little bature walk there as well."
Lake/Beach Getaway (Remodeled)
3-bedroom vacation home just a short walk to Lake Michigan
Terrace/patio

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

9.0 out of 10, Wonderful, (30)
"We stayed for one night since we had a nearby reservation and were coming from Chicago. Location was terrific and we wanted to keep it mind for future booking in the summertime given the proximity to the beach. Really large yard was a plus and accommodations were in nice shape! "
$193 nightly
The price is $220
Oct 13 - Oct 14
Total with taxes and fees
3-bedroom vacation home just a short walk to Lake Michigan
Beach Lake Michigan King Bed Pet Friendly
On the beach

Beach Lake Michigan King Bed Pet Friendly

9.2 out of 10, Wonderful, (9)
"Judy's townhouse was a perfect spot for us to visit our family in Kenosha. We were all able to gather here to visit and enjoy the beautiful lakefront setting! "
Beach Lake Michigan King Bed Pet Friendly
Beautiful and spacious lakefront home! Close to everything!
Exterior detail

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (51)
"A three night stay We were comfortable and pleased with all the amenities. Fishing by the dock, kayaking and enjoying an adult beverage. A magical place to celebrate a new stage. Just one hour away but distant enough to relax the mind "
Beautiful and spacious lakefront home! Close to everything!
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Marina

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

9.4 out of 10, Exceptional, (15)
"Great place to stay! Very nice boat and beautiful area. Host was very prompt in responding and easy to work with. "
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Large Group Retreat w/ secluded party room and private pool
Fridge, microwave, oven, stovetop

Large Group Retreat w/ secluded party room and private pool

7.8 out of 10, Good, (22)
"This property is better than advertised, it was exactly what we were hoping for. Pool area is awesome, all of the teenage boys LOVED the clubhouse, plenty of space to host. Communication with JJ was awesome. Would book again in a heartbeat and will have more stays there."
Large Group Retreat w/ secluded party room and private pool
Entire Beautiful Grove Home
Fridge, microwave, oven, stovetop

Entire Beautiful Grove Home

9.0 out of 10, Wonderful, (11)
"The space of the house was great. Didnt use any of the big back yard. Had a lot of loud music the last two nights. Kept us awake . Even heard with earplugs."
Entire Beautiful Grove Home
A Diamond in the Rough
Outdoor dining

A Diamond in the Rough

9.4 out of 10, Exceptional, (92)
"I will be staying here again in the future. Great place at a great location."
A Diamond in the Rough
Modern Rooftop Retreat in Downtown Mundelein
Microwave, oven, stovetop, dishwasher

Modern Rooftop Retreat in Downtown Mundelein

10.0 out of 10, Exceptional, (1)
"As advertised and close to so many great neighborhood places. "
Modern Rooftop Retreat in Downtown Mundelein
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Smart TV, music library, video library, stereo

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (35)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Spacious 27’ RV on horse farm
Property grounds

Spacious 27’ RV on horse farm

8.6 out of 10, Excellent, (7)
"My stay here was great and I had everything I needed to be comfortable and enjoy myself. I was given a quick tour of the camper and shown how everything works, which was very helpful. I even got shown around the farm and really enjoyed seeing all of the beautiful horses and cute chickens."
$110 nightly
The price is $116
Oct 7 - Oct 8
Total with taxes and fees
Spacious 27’ RV on horse farm
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

Hilton Garden Inn Lake Forest Mettawa

Hilton Garden Inn Lake Forest Mettawa

10/10 Excellent
"Super friendly staff and great bartender. "
Jeremy 2-night trip
Posted 3 days ago
Hilton Garden Inn Lake Forest Mettawa

Find out more about Winthrop Harbor

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 $116 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

This is a VACATION spot with a million dollar view!: This vacation home rental outside of Winthrop Harbor offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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. You’ll find favorite places to visit like Naval Base Great Lakes and Six Flags Great America in the larger area.

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.