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Compare 259 Vacation Homes in Winthrop Harbor with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (15)
"We were really looking forward to the stay, and it exceeded our expectations significantly. I appreciate how they turned a small house that could have just been a bit rundown into a very lovely space all around. "
The price is SAR 349
SAR 805 total
includes taxes & fees
5 Apr - 6 Apr
3-bedroom vacation home just a short walk to Lake Michigan

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

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (22)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (58)
"We drove up from Florida for our son’s Navy graduation. After 2 days on the road, the second day mostly in the freezing ice & snow, it was wonderful to come into this cozy, warm home. I loved the details & character of this older home. The floors squeak a little & there’s some clanging as the heater turns on, but I loved those little bits. It made it feel so much more like a home rather than a hotel. The location was perfect for travel to & from Naval Station Great Lakes. There are plenty of...
The price is SAR 506
SAR 1,144 total
includes taxes & fees
5 Apr - 6 Apr
Quaint Bungalow, near Great Lakes Naval Base

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

9.2 out of 10, Wonderful, (23)
"Is about 2 miles from great lakes for graduation. Layout is different. Sleeps 11 seats 5 or 6 in the living room, big table...half bath in kitchen...is cold in the winter...have to park in the back...walk around to front.can parknon the street but not overnight. The main bathroom with tyb sbower is high but has handrail. It snowed while we were there...owner shoveled sidewalk once. Overall it suit our need..its not high end but it was nice. Plenty of towels...no wash clothes...clean.."
New Your Home Away From Home! - Near Great Lakes Naval Base!!

Harbor Clubhouse 3-Bed 3.5-Bath Modern Waterfront - Pet Friendly

2.0 star property
Harbor Clubhouse 3-Bed 3.5-Bath Modern Waterfront - Pet Friendly

Cute and Cozy Cottage by the Lake! Kayaks! Paddleboard! HUGE Deck w/ Great Views

10.0 out of 10, Exceptional, (24)
"We came in for our annual family ice fishing trip. The host was very responsive and helpful. The location was almost as good as waterfront property. The cozy little house was perfect for what we needed."
Cute and Cozy Cottage by the Lake! Kayaks! Paddleboard! HUGE Deck w/ Great Views

Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed

10.0 out of 10, Exceptional, (79)
"Wonderful and clean home with all that you’ll need for a great getaway! Firepit and outdoor living is on point here!! Would definitely book again!"
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed

Family frndly TwnHm by navy base

2.0 star property
9.8 out of 10, Exceptional, (8)
"This place was as advertised! The house was clean and well stocked with everything you needed. The parking in the back of the house took a moment to find but was easy to access. The proximity to the Navy recruit training base was great and has several great restaurants near by.I would stay here again!"
Family frndly TwnHm by navy base

Lake/Beach Getaway (Remodeled)

9.8 out of 10, Exceptional, (30)
"Loved the view of the lake out the big front window. Perfect place for a family getaway. Apple play on tv worked great. We set up 5 yoga mats in living room and did yoga. Great full length mirror. Cute decor. Couch was comfy and bigger than I thought it would be from the pics. Wish the bunk bed had comfier mattresses - our teen girls were complaining - but they’ll survive lol! Bring coffee for standard coffee maker if you drink coffee. And have fun! Can’t wait to go back this summer. :) "
The price is SAR 563
SAR 1,024 total
includes taxes & fees
24 Mar - 25 Mar
Lake/Beach Getaway (Remodeled)

Charming Family home near Great Lakes Naval Base!

Charming Family home near Great Lakes Naval Base!

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

9.0 out of 10, Wonderful, (24)
"If you are looking for a place to stay for bootcamp graduation this is a great place. It’s minutes from the base. The pictures are accurate and the house had plenty of space for five people. Close to shopping, fast food, and casino. "
The price is SAR 656
SAR 1,099 total
includes taxes & fees
24 Mar - 25 Mar
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

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

The Sunset Manor - Luxe Mansion for Serene retreat

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 2,134
SAR 3,938 total
includes taxes & fees
24 Mar - 25 Mar
The Sunset Manor - Luxe Mansion for Serene retreat

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!

Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls

9.8 out of 10, Exceptional, (26)
"The property worked out perfectly for our family gathering. "
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls

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 SAR 244
SAR 413 total
includes taxes & fees
30 Mar - 31 Mar
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds

9.2 out of 10, Wonderful, (7)
"Perfect location and weather. "
Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds

Charming 2Bd Townhome Near Beach & Base

10.0 out of 10, Exceptional, (19)
"We stayed for Thanksgiving so we could cook our sailor a home cook meal. Everything was as listed. Kelly was very nice and answered all questions. We were upgraded to the 3 bedroom fromthe 2 bedroom "
Charming 2Bd Townhome Near Beach & Base

The Beach Life!— Newly Renovated Beach Home awaits you!

10.0 out of 10, Exceptional, (29)
"The property is lovely. A quick walk to the beach, which even in the winter, was absolutely wonderful to experience. During the first part of the stay there was snow. Bought sleds for everyone to use on the hills. The end of our trip saw all the snow gone and we were able to visit the lighthouse. Not only does the property contain a washer/dryer in the basement, there’s also a 1 car garage we could use. The host(s) are wonderful. The property contained all the little extras a traveling family...
The Beach Life!— Newly Renovated Beach Home awaits you!
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.

6.6 out of 10, (7)
"All features needed, it felt like being at home!!!"
The price is SAR 638
SAR 1,274 total
includes taxes & fees
24 Mar - 25 Mar
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.

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.

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

9.2 out of 10, Wonderful, (23)
"Is about 2 miles from great lakes for graduation. Layout is different. Sleeps 11 seats 5 or 6 in the living room, big table...half bath in kitchen...is cold in the winter...have to park in the back...walk around to front.can parknon the street but not overnight. The main bathroom with tyb sbower is high but has handrail. It snowed while we were there...owner shoveled sidewalk once. Overall it suit our need..its not high end but it was nice. Plenty of towels...no wash clothes...clean.."
New Your Home Away From Home! - Near Great Lakes Naval 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.