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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
5–10 Sept
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5.0 out of 5 average rating, 118 reviews
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Flat in Highland
Swiss Post Apartment - A
2 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Highland
Spacious luxury loft in the heart of Highland!
2 bedrooms, 2 queen beds
1–6 Sept
5.0 out of 5 average rating, 11 reviews
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Loft in Highland
Loft on the Square
3 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 26 reviews
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Home in Highland
The Mulberry Haus
3 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 7 reviews
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Farm stay in Pocahontas
Hilltop Ranch Home on 25 acres bathed in starlight
4 bedrooms, 5 beds
18–23 Sept
4.93 out of 5 average rating, 282 reviews
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Flat in St. Jacob
A Sweet Spot, catering to Traveling Tech/workers
1 bedroom, 1 queen bed
1–6 Sept
4.91 out of 5 average rating, 33 reviews
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Guest suite in Highland
6th St Lofts beautifully designed w/modern comfort
3 bedrooms, 6 beds
6–11 Sept
5.0 out of 5 average rating, 39 reviews
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Loft in Edwardsville
Main Street Loft
3 bedrooms, 4 beds
1–6 Sept
4.93 out of 5 average rating, 46 reviews
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Home in Maryville
Hidden Woods Haven
4 bedrooms, 4 queen beds
14–19 Sept
4.97 out of 5 average rating, 31 reviews
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Home in Caseyville
3BR Private Pond Retreat Near Route 66 -Fire Pit
3 bedrooms, 5 beds
4–9 Sept
4.83 out of 5 average rating, 121 reviews
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Home in Lebanon
Historic Lebanon 2Bed2Bath Home
2 bedrooms, 2 beds
19–24 Oct
5.0 out of 5 average rating, 28 reviews
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Home in Lebanon
The Dickens Retreat | English Cottage Charm
4 bedrooms, 4 beds
25–30 Oct
5.0 out of 5 average rating, 20 reviews
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Townhouse in Belleville
Cheerful 3-Bedroom Townhome | 1.5 Bath | King Bed
3 bedrooms, 5 beds
4–9 Oct
4.89 out of 5 average rating, 266 reviews
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Home in Caseyville
Spacious 4BR Retreat w/ Hot Tub and Pool Table
4 bedrooms, 5 beds
6–11 Sept
4.89 out of 5 average rating, 80 reviews
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Home in Breese
Heritage House, Small Town Comfort, Legion/KC Hall
3 bedrooms, 4 king beds
22–27 Oct
4.96 out of 5 average rating, 112 reviews
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Dome in Worden
Glamping Dome: Bunks, Hot Tub, Brewery & Farm Fun
1 bedroom, 5 beds
7–12 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Edwardsville
Brick B&B - 3Bed 2Full Bath! Downtown Edwardsville
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.9 out of 5 average rating, 173 reviews
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Home in Okawville
Historic Farmhouse on Working Farm
4 bedrooms, 5 beds
1–6 Sept
4.97 out of 5 average rating, 189 reviews