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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
28 Nov – 3 Dec
5.0 out of 5 average rating, 64 reviews
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Top guest favourite
Guest house in New Buffalo
Rainbows End 🌈 Puryear
1 double bed
27 Sept – 2 Oct
4.97 out of 5 average rating, 532 reviews
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Home in La Porte
Spacious Farmhouse Retreat/ Game Room+ More
4 bedrooms, 5 beds
11–16 Oct
New place to stay
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Top guest favourite
Barn in La Porte
Beautiful Barn (sleeps 16)
5 bedrooms, 16 beds
19–24 Sept
4.93 out of 5 average rating, 61 reviews
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Guest favourite
Cabin in Union Pier
McComb's Cabin, Union Pier, MI
2 beds
11–16 Oct
4.94 out of 5 average rating, 394 reviews
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Top guest favourite
Home in La Porte
Private Nature Retreat Abutting MI Harbor Country
5 bedrooms, 10 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 54 reviews
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Guest favourite
Flat in La Porte
8 Mi to Lake Michigan: Creative Retreat w/ Deck!
1 bedroom, 2 beds
20–25 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Michigan City
Escape to nature at The Meadow home in Tryon Farm
3 bedrooms, 3 beds
3–8 Nov
New place to stay
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Top guest favourite
Cabin in New Carlisle
Cozy Cabin Minutes from Michigan's Harbor Country
1 queen bed
20–25 Sept
4.95 out of 5 average rating, 240 reviews
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Top guest favourite
Home in New Carlisle
Millie's Rose Cottage
3 bedrooms, 5 beds
21–26 Sept
4.96 out of 5 average rating, 54 reviews
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Guest favourite
Barn in Three Oaks
Barn of Three Oaks near Lake Michigan/Journeyman
3 bedrooms, 4 beds
20–25 Sept
4.89 out of 5 average rating, 150 reviews
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Guest favourite
Home in New Carlisle
Lakehouse Getaway- Minutes to Notre Dame/Michigan
3 bedrooms, 3 beds
31 Dec – 5 Jan
4.89 out of 5 average rating, 18 reviews
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Top guest favourite
Home in New Buffalo
New Buffalo Getaway: Hot Tub + Fire Pit
4 bedrooms, 6 beds
23–28 Sept
4.96 out of 5 average rating, 57 reviews
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Guest favourite
Farm stay in New Carlisle
Relaxing Glamping Experience in a Tiny Cabin
2 beds
20–25 Sept
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
20–25 Sept
4.98 out of 5 average rating, 173 reviews
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Top guest favourite
Cottage in New Carlisle
Private Beach Home on Hudson Lake New Carlisle
2 bedrooms, 3 beds
20–25 Sept
4.99 out of 5 average rating, 68 reviews
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Top guest favourite
Flat in La Porte
Downtown Daydream - walk to shops + restaurants
2 bedrooms, 3 beds
19–24 Sept
5.0 out of 5 average rating, 98 reviews
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Guest favourite
Home in La Porte
Cozy home on Pine Lake. Huge lakefront yard
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.83 out of 5 average rating, 80 reviews