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Search results; Over 1,000 homes in Rolling Prairie

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Top guest favourite
Home in Rolling Prairie
Rustic & Cozy House in the Woods - Sleeps 10
4 bedrooms, 5 beds, 3 private bathrooms
20–25 Sept
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4.95 out of 5 average rating, 224 reviews
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Top guest favourite
Home in New Carlisle
Luxury home with pool.
5 bedrooms, 7 beds, 3.5 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 64 reviews
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Home in La Porte
Spacious Farmhouse Retreat/ Game Room+ More
4 bedrooms, 5 beds, 3 bathrooms
11–16 Oct
New place to stay
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Top guest favourite
Home in La Porte
HOLY Mother of all Lakehouses
7 bedrooms, 16 beds, 5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in La Porte
Stone's Throw Lake House
3 bedrooms, 3 beds, 1 bathroom
29 Sept – 4 Oct
4.89 out of 5 average rating, 38 reviews
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Superhost
Home in Michigan City
Michigan City Gem! Huge Backyard-Grill-Sleeps 10
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Barn in La Porte
Beautiful Barn (sleeps 16)
5 bedrooms, 16 beds, 3 bathrooms
19–24 Sept
4.93 out of 5 average rating, 61 reviews
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Guest favourite
Barn in Three Oaks
Barn of Three Oaks near Lake Michigan/Journeyman
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.89 out of 5 average rating, 150 reviews
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Guest favourite
Home in La Porte
Living Well
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 52 reviews
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Top guest favourite
Bungalow in New Buffalo
Beautiful garden oasis w/HOT TUB & screened porch!
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 187 reviews
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Top guest favourite
Home in Three Oaks
Dog Friendly Downtown Three Oaks Cottage! Fenced!
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 173 reviews
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Top guest favourite
Home in New Carlisle
Millie's Rose Cottage
3 bedrooms, 5 beds, 1 bathroom
21–26 Sept
4.96 out of 5 average rating, 54 reviews
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Top guest favourite
Cottage in New Carlisle
Private Beach Home on Hudson Lake New Carlisle
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 68 reviews
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Top guest favourite
Home in La Porte
Private Nature Retreat Abutting MI Harbor Country
5 bedrooms, 10 beds, 4 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 54 reviews
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Guest favourite
Tiny home in New Carlisle
Cozy Cabin 2.0 Mins from Michigan’s Harbor Country
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 223 reviews
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Top guest favourite
Home in Three Oaks
Oly's Cottage, Steps from Journeyman and Acorn!
3 bedrooms, 4 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Three Oaks
The Walnut House, Michigan Woods Retreat
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 248 reviews
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Top guest favourite
Home in La Porte
"Party on Pine" Pontoon Boat, Hot Tub & Games!
6 bedrooms, 12 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 97 reviews
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Guest favourite
Chalet in La Porte
Pet friendly, lakefront home sleeps 6 w/ 4 kayaks!
4 beds, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 506 reviews