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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
Home in Highland
Spacious luxury loft in the heart of Highland!
2 bedrooms, 2 queen beds
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
26 Sept – 1 Oct
5.0 out of 5 average rating, 27 reviews
Guest favourite
Flat in Highland
Swiss Post Apartment - A
2 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Highland
The Mulberry Haus
3 bedrooms, 5 beds
10–15 Sept
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
23–28 Oct
4.93 out of 5 average rating, 282 reviews
Top guest favourite
Guest suite in Highland
6th St Lofts beautifully designed w/modern comfort
3 bedrooms, 6 beds
14–19 Sept
5.0 out of 5 average rating, 39 reviews
Guest favourite
Flat in St. Jacob
A Sweet Spot, catering to Traveling Tech/workers
1 bedroom, 1 queen bed
10–15 Sept
4.91 out of 5 average rating, 33 reviews
Farm stay in Staunton
Patriot on Route 66
2 bedrooms, 3 beds
10–15 Sept
New place to stay
Top guest favourite
Home in Lebanon
The Dickens Retreat | English Cottage Charm
4 bedrooms, 4 beds
25–30 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Loft in Pocahontas
Peaceful | Private | Lakeview | Highland-Breese
1 bedroom, 2 beds
13–18 Sept
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Cottage in Pocahontas
Cozy Cottage on 6 Private Acres!
2 bedrooms, 3 beds
26–31 Oct
5.0 out of 5 average rating, 47 reviews
Guest favourite
Flat in Carlyle
Downtown Apartment w/ Gameroom
3 bedrooms, 3 beds
11–16 Sept
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Townhouse in Belleville
Cheerful 3-Bedroom Townhome | 1.5 Bath | King Bed
3 bedrooms, 5 beds
13–18 Sept
4.89 out of 5 average rating, 267 reviews
Guest favourite
Home in Greenville
Cozy Home on College Ave
2 bedrooms, 2 beds
11–16 Oct
4.96 out of 5 average rating, 246 reviews
Guest favourite
Home in Edwardsville
Charming Edwardsville Home: Walk to Downtown!
3 bedrooms, 5 beds
14–19 Sept
4.81 out of 5 average rating, 64 reviews
Guest favourite
Home in Caseyville
Spacious 4BR Retreat w/ Hot Tub and Pool Table
4 bedrooms, 5 beds
10–15 Sept
4.89 out of 5 average rating, 81 reviews
Top guest favourite
Home in Carlyle
Dam side Getaway
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Guest house in Pocahontas
Cozy Loft near Winery & Venues
1 bedroom, 1 queen bed
13–18 Sept
5.0 out of 5 average rating, 7 reviews