Winthrop Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

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, (90)
"We had a wonderful stay at this lakefront property. The location is peaceful and scenic—perfect for relaxing or spending time outdoors. The host was incredibly welcoming, responsive, and made sure everything was perfect. Highly recommend for anyone looking for a great getaway!"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
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, (8)
The price is ￥27,506
￥75,365 total
includes taxes & fees
Oct 20 - Oct 21
North Chi retreat – Navy, Sauna, Tiki Bar, Games
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
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"
The price is ￥60,543
￥91,414 total
includes taxes & fees
Sep 29 - Sep 30
This is a VACATION spot with a million dollar view!
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, (245)
"Beautiful view, wonderful house. Great morings with coffee on balcony!!"
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
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
Cozy RV in our land with community private beach, fire pit, bring your boat.
Property grounds

Cozy RV in our land with community private beach, fire pit, bring your boat.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a nice time visiting Antioch, IL. The property clean, quiet and well maintained. The camper was adorable and very comfortable. Thank you!"
Cozy RV in our land with community private beach, fire pit, bring your boat.
Charming 3-bedroom house in Grayslake
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (17)
"Fells like home very cozy calm area definitely a get away relaxing place "
The price is ￥39,615
￥80,641 total
includes taxes & fees
Oct 1 - Oct 2
Charming 3-bedroom house in Grayslake
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
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
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! "
The price is ￥20,181
￥40,721 total
includes taxes & fees
Sep 29 - Sep 30
3-bedroom vacation home just a short walk to Lake Michigan
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
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, (13)
"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
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, (21)
"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
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, (28)
"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, (39)
"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
The Randolph Hotel Apt 201
Marina

The Randolph Hotel Apt 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. "
The price is ￥16,818
￥76,447 total
includes taxes & fees
Oct 5 - Oct 6
The Randolph Hotel Apt 201
Marina Life II - 28 Carver @ Reef Point Marina
Property grounds

Marina Life II - 28 Carver @ Reef Point Marina

9.6 out of 10, Exceptional, (48)
"We stayed for two nights at the house boat. The host communicated very efficiently and was nice. Even though the boat is small, it was cozy and we never felt cramped. We loved the amenities that are included in the marina. Walking distance from downtown so there was plenty to do. Would stay here again. "
Marina Life II - 28 Carver @ Reef Point Marina
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!!
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
"The hotel is beautifully decorated, every detail is coordinated throughout the building. Staff was very welcoming when we arrived. Common Hotel breakfast was served, and staff was friendly. We travel through the area often and will plan to return when we're back through again."
Amber 1-night trip
Posted 3 days ago
The Inn on Sheridan

Find out more about Winthrop Harbor

Find out more about Winthrop Harbor

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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?

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.