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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
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
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
20–25 Sept
4.93 out of 5 average rating, 61 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
Barn in New Carlisle
Be Our "Country" Guest
2 bedrooms, 4 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 172 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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Top guest favourite
Home in New Carlisle
Millie's Rose Cottage
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 54 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
27 Sept – 2 Oct
4.91 out of 5 average rating, 249 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
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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, 241 reviews
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Guest favourite
Home in La Porte
Private Nature Retreat Abutting MI Harbor Country
2 bedrooms, 2 beds
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
28 Sept – 3 Oct
5.0 out of 5 average rating, 64 reviews
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Home in Rolling Prairie
Harbor Country 7 acres Htd pool
3 bedrooms, 3 beds
23–28 Sept
4.71 out of 5 average rating, 14 reviews
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Guest favourite
Yurt in Buchanan
Off Grid Yurt Glamping on Permaculture Homestead
1 queen bed
20–25 Sept
4.97 out of 5 average rating, 230 reviews
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Top guest favourite
Flat in La Porte
Downtown Daydream - walk to shops + restaurants
2 bedrooms, 3 beds
21–26 Sept
5.0 out of 5 average rating, 98 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
27 Sept – 2 Oct
4.97 out of 5 average rating, 38 reviews
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Top guest favourite
Home in La Porte
Lake front 4 bedroom w/pier Best view of the lake
4 bedrooms, 7 beds
11–16 Oct
4.88 out of 5 average rating, 33 reviews