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Search results; 745 homes in Winthrop Harbor

Guest favourite
Guest suite in Zion
Cozy mother inlaw suite. Private. Next to beach.
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 254 reviews
Top guest favourite
Home in Winthrop Harbor
Harbor Haven/Near Base/Great America/Game Room/Gym
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
4.98 out of 5 average rating, 54 reviews
Home in Zion
Secluded Retreat with Workspaces & Nature Trails
3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.66 out of 5 average rating, 113 reviews
Top guest favourite
Home in Winthrop Harbor
The Harbor House - Amazing!
3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 36 reviews
Home in Zion
Beautiful & Cozy, Sears Home.
5 bedrooms, 9 beds, 2 bathrooms
9–14 Aug
4.7 out of 5 average rating, 114 reviews
Guest favourite
Room in Winthrop Harbor
3. Modern Retreat
1 double bed, 3 bathrooms
29 Aug – 3 Sept
4.97 out of 5 average rating, 67 reviews
Guest favourite
Room in Zion
Homie's House
1 bed, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 21 reviews
Superhost
Dome in Pleasant Prairie
Unique Dome Home Golf Range Experience by the Lake
4 bedrooms, 8 beds, 2.5 bathrooms
15–20 Aug
4.86 out of 5 average rating, 112 reviews
Guest favourite
Flat in Waukegan
The Rooftop Haven
2 bedrooms, 2 queen beds, 1.5 bathrooms
11–16 Sept
4.95 out of 5 average rating, 148 reviews
Top guest favourite
Home in Waukegan
Kalo House | Mid-Century Modern Retreat with Pool
4 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Beach Park
B’s Farmhouse Cottage 2-bedroom duplex.
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 273 reviews
Guest favourite
Room in Winthrop Harbor
2. Modern Retreat
1 bed, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Pleasant Prairie
Breathtaking view @lakefront
3 bedrooms, 8 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Kenosha
Little House by the BIG LAKE
3 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Salem Lakes
Twin Pines at Cross Lake
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.93 out of 5 average rating, 40 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds, 1 bathroom
17–22 Oct
4.95 out of 5 average rating, 190 reviews
Guest favourite
Home in Waukegan
Modern & Spacious Retreat • Fast Wi-Fi •Desk• Yard
4 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.93 out of 5 average rating, 27 reviews
Superhost
Home in Bristol
Aspen on Shangrila | Lakefront, hot tub & golf sim
6 bedrooms, 10 beds, 4 bathrooms
14–19 Aug
New place to stay