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Search results; Over 1,000 homes in Highland

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Top guest favourite
Home in Highland
Beautiful craftsman style home, built in 1930.
6 bedrooms, 8 beds, 3 private bathrooms
18–23 Oct
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5.0 out of 5 average rating, 121 reviews
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Guest favourite
Flat in Highland
Swiss Post Apartment - A
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Highland
Spacious luxury loft in the heart of Highland!
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Loft in Highland
Loft on the Square
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 27 reviews
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Guest favourite
Home in Highland
The Mulberry Haus
3 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Farm stay in Pocahontas
Hilltop Ranch Home on 25 acres bathed in starlight
4 bedrooms, 5 beds, 3.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 283 reviews
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Top guest favourite
Guest suite in Highland
6th St Lofts beautifully designed w/modern comfort
3 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 39 reviews
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Guest favourite
Flat in St. Jacob
A Sweet Spot, catering to Traveling Tech/workers
1 bedroom, 1 queen bed, 1 bathroom
17–22 Sept
4.91 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Carlyle
The Nest @ OliveOaks near Breese and Carlyle
4 bedrooms, 5 beds, 3 bathrooms
19–24 Oct
4.97 out of 5 average rating, 64 reviews
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Top guest favourite
Home in Lebanon
Historic Lebanon 2Bed2Bath Home
2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Home in Mascoutah
The Doll House
3 bedrooms, 3 beds, 1 bathroom
20–25 Oct
4.96 out of 5 average rating, 494 reviews
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Top guest favourite
Home in Lebanon
The Dickens Retreat | English Cottage Charm
4 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Boutique hotel in Breese
Breese Inn - Executive Deluxe Room-No added fees!
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 53 reviews
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Top guest favourite
Flat in Greenville
Stay on the Historic Town Square in Greenville, IL
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.99 out of 5 average rating, 92 reviews
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Guest favourite
Home in Caseyville
Spacious 4BR Retreat w/ Hot Tub and Pool Table
4 bedrooms, 5 beds, 3 bathrooms
16–21 Sept
4.89 out of 5 average rating, 81 reviews
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Superhost
Home in Edwardsville
Brand New 3 bedroom home fully furnished
3 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.82 out of 5 average rating, 100 reviews
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Guest favourite
Home in Caseyville
3BR Private Pond Retreat Near Route 66 -Fire Pit
3 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
4.83 out of 5 average rating, 121 reviews
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Top guest favourite
Loft in Pocahontas
Peaceful | Private | Lakeview | Highland-Breese
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 57 reviews
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Guest favourite
Home in Edwardsville
Brick B&B - 3Bed 2Full Bath! Downtown Edwardsville
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.9 out of 5 average rating, 175 reviews