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Search results; 591 homes

Photo 1 of 29
Top guest favourite
Home in Sheboygan
Modern Lakeshore Home with Treehouse
4 bedrooms, 8 beds, 3.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 37 reviews
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Guest favourite
Home in Sheboygan
Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub
4 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
4.92 out of 5 average rating, 64 reviews
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Superhost
Home in Sheboygan
Black River Retreat
4 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.83 out of 5 average rating, 48 reviews
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Guest favourite
Home in Sheboygan
Pelican Point - Private Retreat
4 bedrooms, 8 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 8 reviews
Photo 1 of 29
Top guest favourite
Home in Oostburg
Lake Michigan Beach Home by Frank Lloyd Wright pro
2 bedrooms, 3 beds, 1.5 bathrooms
27 Oct – 3 Nov
4.96 out of 5 average rating, 184 reviews
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Top guest favourite
Home in Oostburg
Outdoor Sauna | 6-BRs | Kohler-Andrae
6 bedrooms, 11 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 119 reviews
Photo 1 of 22
Top guest favourite
Guest house in Oostburg
Beach House
2 bedrooms, 2 double beds, 1 bathroom
18–23 Oct
4.92 out of 5 average rating, 431 reviews
Photo 1 of 29
Top guest favourite
Home in Sheboygan
Woodland Creek Retreat: explore & relax!
3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 251 reviews
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Home in Oostburg
Awesome Game Room-XL Beachfront HM-Pool Table, ETC
4 bedrooms, 8 beds, 3 bathrooms
27 Sept – 2 Oct
4.53 out of 5 average rating, 40 reviews
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Guest favourite
Home in Sheboygan
Stylish Getaway | Cozy Vibes | Perfect Girls Trip
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.94 out of 5 average rating, 226 reviews
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Guest favourite
Cottage in Oostburg
Find your Autumn calm at Beachdaze
3 bedrooms, 7 beds, 1.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Sheboygan
Feel at home in this 3 bedroom, 2 bath home.
3 bedrooms, 3 beds, 2 bathrooms
29 Sept – 4 Oct
4.98 out of 5 average rating, 40 reviews
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Top guest favourite
Flat in Sheboygan
Modern Upstairs Apt - Steps from Lake Michigan
2 bedrooms, 2 beds, 2 bathrooms
1–6 Nov
4.99 out of 5 average rating, 277 reviews
Photo 1 of 29
Top guest favourite
Flat in Sheboygan
Riverfront Loft - Fantastic location
1 bedroom, 4 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 42 reviews
Photo 1 of 29
Guest favourite
Home in Oostburg
Hello Pumpkin! Fall Dates available at Surfdaze!
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 31 reviews
Photo 1 of 29
Top guest favourite
Home in Sheboygan
Luxury Pool Retreat-2 Acres-Near Whistling Straits
4 bedrooms, 8 beds, 4 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Top guest favourite
Cabin in Oostburg
Rare Find! Huge Beach & Luxe Woodsy Cabin
3 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.92 out of 5 average rating, 49 reviews
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Top guest favourite
Flat in Sheboygan
Lovely modern home with fire pit
1 bedroom, 1 queen bed, 1.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 55 reviews