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Search results; Over 1,000 homes in Highland

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, 119 reviews
Guest favourite
Flat in Highland
Swiss Post Apartment - A
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Highland
The Mulberry Haus
3 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Highland
Spacious luxury loft in the heart of Highland!
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 11 reviews
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
Guest favourite
Farm stay in Pocahontas
Hilltop Ranch Home on 25 acres bathed in starlight
4 bedrooms, 5 beds, 3.5 bathrooms
23–28 Oct
4.93 out of 5 average rating, 282 reviews
Guest favourite
Flat in St. Jacob
A Sweet Spot, catering to Traveling Tech/workers
1 bedroom, 1 queen bed, 1 bathroom
10–15 Sept
4.91 out of 5 average rating, 33 reviews
Guest favourite
Home in Caseyville
3BR Private Pond Retreat Near Route 66 -Fire Pit
3 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
4.83 out of 5 average rating, 121 reviews
Top guest favourite
Guest suite in Highland
6th St Lofts beautifully designed w/modern comfort
3 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 39 reviews
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
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, 22 reviews
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, 174 reviews
Top guest favourite
Home in Maryville
Hidden Woods Haven
4 bedrooms, 4 queen beds, 3 bathrooms
14–19 Sept
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Caseyville
Spacious 4BR Retreat w/ Hot Tub and Pool Table
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
4.89 out of 5 average rating, 81 reviews
Top guest favourite
Home in Lebanon
Historic Lebanon 2Bed2Bath Home
2 bedrooms, 2 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Loft in Pocahontas
Peaceful | Private | Lakeview | Highland-Breese
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 56 reviews
Home in Belleville
"Saratoga Haven x4"
4 bedrooms, 7 beds, 2 bathrooms
12–17 Sept
New place to stay
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, 90 reviews
Guest favourite
Home in Beckemeyer
The Carol Inn
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 99 reviews