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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
Home in Three Oaks
Oly's Cottage, Steps from Journeyman and Acorn!
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 27 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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Superhost
Home in La Porte
Living Well
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.85 out of 5 average rating, 52 reviews
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Guest favourite
Home in New Buffalo
New buffalo Farmstead main home pool hot tub
6 bedrooms, 8 queen beds, 2 bathrooms
30 Oct – 4 Nov
4.94 out of 5 average rating, 143 reviews
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Top guest favourite
Home in La Porte
HOLY Mother of all Lakehouses
7 bedrooms, 16 beds, 5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 12 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
1–6 Oct
5.0 out of 5 average rating, 33 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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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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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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Guest favourite
Flat in La Porte
Mainstay Mini
1 queen bed, 1 bathroom
1–6 Dec
4.93 out of 5 average rating, 44 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
18–23 Oct
5.0 out of 5 average rating, 98 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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Superhost
Home in South Bend
Hot Tub | 2 Game Rooms | Indoor Playground | 17ppl
5 bedrooms, 12 beds, 3 bathrooms
4–9 Oct
New place to stay
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Guest favourite
Home in La Porte
New! Modern lakeside retreat-hot tub-trails-kayak
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 33 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
4.95 out of 5 average rating, 55 reviews
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Top guest favourite
Home in New Buffalo
5BR on 5 Acres w/ Hot Tub, Pickleball, Arcade
5 bedrooms, 9 beds, 3 bathrooms
1–6 Nov
4.96 out of 5 average rating, 101 reviews