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Check prices for these dates

Next weekend
7 Mar - 9 Mar
In two weeks
14 Mar - 16 Mar
In one month
28 Mar - 30 Mar
In two months
25 Apr - 27 Apr

Compare 214 Vacation Homes in Winthrop Harbor with updated reviews, rates, and availability.

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

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

9.2 out of 10, Wonderful, (22)
"It’s a great location to Great Lakes navy grad. I was impressed that they supplied trash bags and paper products. One room looked to be an addition, it got a little cold. Heaters were provided tho. I didn’t like not having access codes til I was in Chicago and trying to reach owners. All in all, it was great. "
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Property grounds

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

9.6 out of 10, Exceptional, (81)
"Exactly as desribed. Very clean and quiet. Easy to find and very good good communication"
The price is AED 213
AED 367 total
includes taxes & fees
28 Feb - 1 Mar
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
IVP Manor House Close to Lake Beach & Naval Base
Fridge, microwave, oven, stovetop

IVP Manor House Close to Lake Beach & Naval Base

9.6 out of 10, Exceptional, (51)
"We needed a good centralized location for Thanksgiving with our relatives. This house was the perfect location, was very spacious, very clean, and comfortable beds and pillows. Would definitely stay again, thank you for your hospitality! "
IVP Manor House Close to Lake Beach & Naval Base
Roxan Corner
Terrace/patio

Roxan Corner

8.4 out of 10, Very Good, (32)
"We were very pleased with the location of the home. The property seemed to be well maintained and accomodating. The only downfall was that it seemed very pricey for the time of year"
Roxan Corner
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (21)
"This property was perfect for several family members to stay & be comfortable, especially with having their own bathroom. It was very clean & spacious. It is a unique & awesome property. I was in touch with the host. She was delightful & quick to reply. The neighborhood is very nice. The location was perfect to get to the base & close to the cute town of Libertyville. I would definitely stay here again! "
Riverfront Libertyville Retreat w/ Outdoor Kitchen
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, (5)
"We stayed here when our daughter graduated from the Navy. House is as described and sticked/furnished with all you need or would expect. House was clean. Neighborhood seemed a little "sketchy" but we had zero issues or concerns while we were there. If you are coming for a Navy graduation location is good. Less than 10 mintues to base except on graduatiin morning. Traffic is horrendous but were still able to get from home and in our seats in less than 90 minutes. Would recommend and stay again"
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, (233)
"This property is a TRUE GEM! The views and open-spaced layouts are amazing. The amenities are countless and plentiful; all that you'd want. No matter the season, this is a must stay. Everything was beautiful, clean, organized, well communicated, and just plain easy. A exemplary. Awesome Host. I will definitely be returning every year! "
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Quaint Bungalow, near Great Lakes Naval Base
TV, books

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (56)
"Got to stay in this wonderful home while visiting my son and his family. I loved it!"
The price is AED 496
AED 1,135 total
includes taxes & fees
6 Mar - 7 Mar
Quaint Bungalow, near Great Lakes Naval Base
Modern Lakeside Villa
Outdoor spa tub

Modern Lakeside Villa

10.0 out of 10, Exceptional, (15)
"Great home and beautiful location. Thank you!"
Modern Lakeside Villa
3-bedroom vacation home just a short walk to Lake Michigan
Terrace/patio

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

9.6 out of 10, Exceptional, (14)
"Great stay by the snow covered beach great communication"
The price is AED 342
AED 789 total
includes taxes & fees
2 Mar - 3 Mar
3-bedroom vacation home just a short walk to Lake Michigan
Adorable 2-bedroom home near downtown Grayslake!
Exterior

Adorable 2-bedroom home near downtown Grayslake!

10.0 out of 10, Exceptional, (22)
"Cute and cozy. Very clean. Hosted a successful Thanksgiving dinner with local family. Had everything we needed (we didn't cook a turkey, though). Also spent quality time with our Navy boot camp graduate! Great house!"
Adorable 2-bedroom home near downtown Grayslake!
Entire Lake Villa Home!
Beach nearby

Entire Lake Villa Home!

9.4 out of 10, Exceptional, (37)
"We stayed over the weekend to attend family events. The location is very near where we needed it to be. If you are here to go to Six Flags or Great Lakes Naval Base. You should be good as it’s about 20 minutes out. Quiet neighborhood"
Entire Lake Villa Home!
Charming 2-bedroom house with a pier and kayaks in Paddock Lake
Miscellaneous

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

10.0 out of 10, Exceptional, (2)
"Cute, clean, and a quick and easy drive to Kenosha. We enjoyed our stay. Highly recommend!"
The price is AED 404
AED 709 total
includes taxes & fees
3 Mar - 4 Mar
Charming 2-bedroom house with a pier and kayaks in Paddock Lake
2bed /1bath TH - 7min Six Flags, 14min Navy Base
Microwave, oven, stovetop, dishwasher

2bed /1bath TH - 7min Six Flags, 14min Navy Base

10.0 out of 10, Exceptional, (4)
"The listing online was very accurate to what we arrived. And experienced everything we needed was pretty much on hand easily.The best accommodations I could have asked for"
The price is AED 294
AED 854 total
includes taxes & fees
1 Mar - 2 Mar
2bed /1bath TH - 7min Six Flags, 14min Navy Base
Captain's Quarters 2/2 Lake Life Dream Home
Miscellaneous

Captain's Quarters 2/2 Lake Life Dream Home

Captain's Quarters 2/2 Lake Life Dream Home
Huge 6-bedroom house with WiFi, fitness, Games and Comfort in Great Lake
Fridge, microwave, oven, stovetop

Huge 6-bedroom house with WiFi, fitness, Games and Comfort in Great Lake

10.0 out of 10, Exceptional, (2)
"Check in was a breeze. The house was perfect for our family. Just enough room for 2 grandmothers two couples and a sibling with kiddo. The host was very attentive and even had snacks for us when we arrived. Which was nice b/c we had been traveling the entire day. The house was in a great location not far to get to the Great Lakes base for my son’s and nephews graduation. The house was spacious enough and cozy for our family to gather around and have great conversations lol we had a lot of fun...
Huge 6-bedroom house with WiFi, fitness, Games and Comfort in Great Lake
SPACIOUS and Stylish Lakefront Retreat, Views, Fireworks!, Fire pit
Property grounds

SPACIOUS and Stylish Lakefront Retreat, Views, Fireworks!, Fire pit

9.4 out of 10, Exceptional, (28)
"Perfect house for a girl’s weekend. There were 11 of us and we all fit comfortably!"
SPACIOUS and Stylish Lakefront Retreat, Views, Fireworks!, Fire pit
Beautiful Spacious Escape On The Chain O'Lakes
Outdoor dining

Beautiful Spacious Escape On The Chain O'Lakes

9.4 out of 10, Exceptional, (56)
"Everyone enjoyed the view "
Beautiful Spacious Escape On The Chain O'Lakes
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Smart TV, stereo

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

9.0 out of 10, Wonderful, (23)
"My wife and I had a wonderful stay for our son's graduation for boot camp. The house was located 5 minutes from Great Lakes, and our host was very responsive and accommodating whenever we needed anything."
The price is AED 643
AED 1,039 total
includes taxes & fees
30 Mar - 31 Mar
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Enjoy Spectacular Sunset Views ☀️ On True Lakefront
Beach

Enjoy Spectacular Sunset Views ☀️ On True Lakefront

10.0 out of 10, Exceptional, (53)
"Had a wonderful time at this property over President's Day weekend. It was cozy and well-appointed, and the view is amazing, even if it was mostly a snowy frozen lake! We got a nice sunset the last evening. We were provided many amenities like coffee and some snacks, and we had what we needed in the kitchen to make yummy meals. The beds and pillows were great, and the bathrooms were nice. The ice maker line might have been frozen, but there were ice cube trays and it was fine. Having the...
Enjoy Spectacular Sunset Views ☀️ On True Lakefront
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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Other property types in Winthrop Harbor

Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
Exterior

Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.

6.6 out of 10, (7)
"All features needed, it felt like being at home!!!"
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Miscellaneous

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

10.0 out of 10, Exceptional, (65)
"We stayed here while skiing in Wilmot. Easy drive there and back. Plenty of room upstairs and down stairs to hang out. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
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, (233)
"This property is a TRUE GEM! The views and open-spaced layouts are amazing. The amenities are countless and plentiful; all that you'd want. No matter the season, this is a must stay. Everything was beautiful, clean, organized, well communicated, and just plain easy. A exemplary. Awesome Host. I will definitely be returning every year! "
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
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.