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Search results; Over 1,000 homes in Highland

Top guest favourite
Guest suite in Highland
6th St Lofts beautifully designed w/modern comfort
3 bedrooms, 6 beds, 2 private bathrooms
6–11 Sept
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5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Highland
Beautiful craftsman style home, built in 1930.
6 bedrooms, 8 beds
16–21 Aug
5.0 out of 5 average rating, 115 reviews
Guest favourite
Home in Highland
Spacious luxury loft in the heart of Highland!
2 bedrooms, 2 queen beds
9–14 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Highland
Swiss Post Apartment - B
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Farm stay in Pocahontas
Hilltop Ranch Home on 25 acres bathed in starlight
4 bedrooms, 5 beds
16–21 Aug
4.93 out of 5 average rating, 280 reviews
Top guest favourite
Loft in Highland
Loft on the Square
3 bedrooms, 3 beds
23–28 Aug
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Highland
The Mulberry Haus
3 bedrooms, 5 beds
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Greenville
Cozy Home on College Ave
2 bedrooms, 2 beds
9–14 Aug
4.96 out of 5 average rating, 240 reviews
Top guest favourite
Cottage in Pocahontas
Cozy Cottage on 6 Private Acres!
2 bedrooms, 3 beds
21–26 Aug
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Loft in Pocahontas
Peaceful | Private | Lakeview | Highland-Breese
1 bedroom, 2 beds
9–14 Aug
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Home in Maryville
Hidden Woods Haven
4 bedrooms, 4 queen beds
17–22 Aug
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Beckemeyer
The Carol Inn
2 bedrooms, 3 beds
23–28 Aug
4.96 out of 5 average rating, 96 reviews
Top guest favourite
Home in Keyesport
Vintage Lakeside Cottage in Keyesport
2 bedrooms, 3 beds
18–23 Aug
4.97 out of 5 average rating, 62 reviews
Top guest favourite
Home in Glen Carbon
Sunset Cottage - 2 King beds! Downtown Glen Carbon
2 bedrooms, 2 king beds
9–14 Aug
4.93 out of 5 average rating, 112 reviews
Guest favourite
Home in Caseyville
The Maple Cottage
2 bedrooms, 3 beds
6–11 Sept
4.87 out of 5 average rating, 121 reviews
Top guest favourite
Home in Lebanon
Historic Lebanon 2Bed2Bath Home
2 bedrooms, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Staunton
2br home, private yard hot tub
2 bedrooms, 2 beds
9–14 Aug
4.87 out of 5 average rating, 150 reviews
Top guest favourite
Cottage in Belleville
The Historic Garfield Inn
1 bedroom, 1 double bed
10–15 Aug
4.96 out of 5 average rating, 610 reviews
Superhost
Cabin in Staunton
The Lodge On The Lake #1
3 bedrooms, 3 beds
10–15 Aug
5.0 out of 5 average rating, 7 reviews