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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
Guest house in New Buffalo
Rainbows End 🌈 Puryear
1 double bed, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 532 reviews
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Top guest favourite
Barn in New Carlisle
Be Our "Country" Guest
2 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
4.98 out of 5 average rating, 171 reviews
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Top guest favourite
Home in New Carlisle
Millie's Rose Cottage
3 bedrooms, 5 beds, 1 bathroom
27 Sept – 2 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
20–25 Sept
4.95 out of 5 average rating, 240 reviews
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Guest favourite
Farm stay in New Carlisle
Relaxing Glamping Experience in a Tiny Cabin
2 beds, 1 bathroom
27 Sept – 2 Oct
4.91 out of 5 average rating, 249 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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Guest favourite
Home in La Porte
Cozy home on Pine Lake. Huge lakefront yard
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.83 out of 5 average rating, 80 reviews
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Guest favourite
Home in La Porte
Private Nature Retreat Abutting MI Harbor Country
2 bedrooms, 2 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 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
28 Sept – 3 Oct
5.0 out of 5 average rating, 64 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 Bridgman
The Schmidt House
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 109 reviews
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Top guest favourite
Home in La Porte
3-BR cottage w/ hot tub
3 bedrooms, 5 beds, 1 bathroom
17–22 Nov
4.96 out of 5 average rating, 82 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
27 Sept – 2 Oct
4.97 out of 5 average rating, 38 reviews
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Top guest favourite
Home in Three Oaks
The Bank- Historic Charm | Modern Stay
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 33 reviews
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Flat in La Porte
Downtown Daydream - walk to shops + restaurants
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 98 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
20–25 Sept
4.93 out of 5 average rating, 544 reviews