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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
17–22 Sept
5.0 out of 5 average rating, 8 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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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
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
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
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
Guest house in Pocahontas
Cozy Loft near Winery & Venues
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 8 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
Cottage in Pocahontas
Cozy Cottage on 6 Private Acres!
2 bedrooms, 3 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 48 reviews
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Superhost
Barn in Alhambra
Boho Barn Loft Countryside Getaway
5 beds, 1 bathroom
17–22 Sept
4.83 out of 5 average rating, 92 reviews
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Guest favourite
Home in Greenville
Cozy Home on College Ave
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 249 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
Home in Maryville
Hidden Woods Haven
4 bedrooms, 4 queen beds, 3 bathrooms
18–23 Sept
4.97 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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Farm stay in Staunton
Patriot on Route 66
2 bedrooms, 3 beds, 1 bathroom
17–22 Sept
New place to stay
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Guest favourite
Home in Caseyville
The Maple Cottage
2 bedrooms, 3 beds, 1 bathroom
8–13 Oct
4.87 out of 5 average rating, 127 reviews
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Superhost
Home in Edwardsville
Brand New 3 bedroom home fully furnished
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.82 out of 5 average rating, 100 reviews