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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
18–23 Oct
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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
Barn in New Carlisle
Be Our "Country" Guest
2 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.98 out of 5 average rating, 173 reviews
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Guest favourite
Home in New Carlisle
Lakehouse Getaway- Minutes to Notre Dame/Michigan
3 bedrooms, 3 beds, 2 bathrooms
31 Dec – 5 Jan
4.89 out of 5 average rating, 18 reviews
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Top guest favourite
Guest house in New Buffalo
Rainbows End 🌈 Puryear
1 double bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 532 reviews
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Top guest favourite
Home in New Carlisle
Millie's Rose Cottage
3 bedrooms, 5 beds, 1 bathroom
4–9 Oct
4.96 out of 5 average rating, 54 reviews
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Top guest favourite
Cabin in New Carlisle
Cozy Cabin Minutes from Michigan's Harbor Country
1 queen bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 241 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
9–14 Nov
4.94 out of 5 average rating, 54 reviews
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Top guest favourite
Home in New Carlisle
The Hudson 14mi to New Buffalo!
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 64 reviews
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Guest favourite
Farm stay in New Carlisle
Relaxing Glamping Experience in a Tiny Cabin
2 beds, 1 bathroom
4–9 Oct
4.91 out of 5 average rating, 250 reviews
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Top guest favourite
Cabin in New Carlisle
Cozy Cabin 3.0 Mins from Michigan Harbor Country
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 22 reviews
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Top guest favourite
Flat in La Porte
Second Floor Apartment sitting on Pine Lake
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 544 reviews
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Top guest favourite
Barn in La Porte
Beautiful Barn (sleeps 16)
5 bedrooms, 16 beds, 3 bathrooms
1–6 Oct
4.93 out of 5 average rating, 61 reviews
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Superhost
Home in Michigan City
Michigan City Gem! Huge Backyard-Grill-Sleeps 10
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Tiny home in Michigan City
The Pocket House - A Getaway Surrounded by Nature
1 bedroom, 4 beds, 1 bathroom
12–17 Oct
4.97 out of 5 average rating, 38 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
4–9 Oct
4.89 out of 5 average rating, 150 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
4–9 Oct
4.98 out of 5 average rating, 173 reviews
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Guest favourite
Home in La Porte
La Casita De Lago
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 131 reviews