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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, 120 reviews
Guest favourite
Home in Highland
Spacious luxury loft in the heart of Highland!
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 12 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
Home in Highland
The Mulberry Haus
3 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Highland
Swiss Post Apartment - A
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in Highland
6th St Lofts beautifully designed w/modern comfort
3 bedrooms, 6 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 39 reviews
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
Guest favourite
Flat in St. Jacob
A Sweet Spot, catering to Traveling Tech/workers
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept
4.91 out of 5 average rating, 33 reviews
Guest favourite
Home in Belleville
Charming 3BR/2BA Retreat w/ King Bed & Fenced Yard
3 bedrooms, 5 beds, 2 bathrooms
5–10 Nov
4.9 out of 5 average rating, 90 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, 23 reviews
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, 56 reviews
Guest favourite
Flat in Carlyle
Downtown Apartment w/ Gameroom
3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Oct
4.96 out of 5 average rating, 25 reviews
Guest favourite
Home in Caseyville
The Maple Cottage
2 bedrooms, 3 beds, 1 bathroom
8–13 Oct
4.87 out of 5 average rating, 126 reviews
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
Home in Greenville
Heavenly Hideaway
4 bedrooms, 13 beds, 3 bathrooms
15–20 Sept
4.75 out of 5 average rating, 4 reviews
Top guest favourite
Home in Edwardsville
Cozy Chicken Cottage
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 107 reviews
Guest favourite
Loft in Edwardsville
Main Street Loft
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.94 out of 5 average rating, 49 reviews
Guest favourite
Home in Caseyville
Spacious 4BR Retreat w/ Hot Tub and Pool Table
4 bedrooms, 5 beds, 3 bathrooms
15–20 Sept
4.89 out of 5 average rating, 81 reviews
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