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Search results; Over 1,000 homes

Top guest favourite
Barn in Wingecarribee Shire Council
Farm stay unique barn in Southern Highlands
1 bedroom, 2 beds, 1 private bathroom
27 Sept – 2 Oct
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4.91 out of 5 average rating, 91 reviews
Top guest favourite
Home in Bowral
The Croft - Enchanting Bowral stone cottage
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 81 reviews
Luxe
Home in Sutton Forest
“Southern Highlands Estate”, Private Rural Oasis.
4 bedrooms, 4 beds, 4 bathrooms
14–19 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Woodlands
Cuttaway Cottage
3 bedrooms, 3 king beds, 2 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 68 reviews
Top guest favourite
Home in Sutton Forest
Sutton View - Sweeping Hilltop Views
4 bedrooms, 7 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Mittagong
Yambora ' Luxe Hideaway' Minutes to Bowral
3 bedrooms, 4 beds, 2 bathrooms
24–29 Oct
5.0 out of 5 average rating, 12 reviews
Home in Burradoo
Birchgrove | Entire Country Home & Loft
7 bedrooms, 10 beds, 5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Glenquarry
Rustic Luxury at The Old Dairy – A Stunning Escape
3 bedrooms, 3 beds, 3 bathrooms
14–19 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Tiny home in Moss Vale
Woodvilla
2 bedrooms, 4 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Burradoo
Open Country Homestead - New Luxury accommodation
5 bedrooms, 6 beds, 3 bathrooms
12–17 Oct
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Cottage in Exeter
Southern Highlands - "Woodbury" Lodge Exeter
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 369 reviews
Top guest favourite
Home in Joadja
The Lodge - a spectacular chalet-style residence
6 bedrooms, 12 beds, 5 bathrooms
21–26 Nov
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Bowral
Beautiful Bendooley Garden Cottage
4 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 93 reviews
Top guest favourite
Cottage in Bundanoon
Pear Tree Cottage
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.95 out of 5 average rating, 418 reviews
Top guest favourite
Guest suite in Mittagong
Unique Southern Highlands Cottage
2 bedrooms, 4 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Bowral
Chateau Bowral – Luxury Southern Highlands Estate
4 bedrooms, 7 beds, 3 bathrooms
25–30 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cottage in Mittagong
Laurel Cottage, Southern Highlands
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 344 reviews
Guest favourite
Home in Bowral
The Cottage: luxury & Heritage in Bowral's heart
3 bedrooms, 3 king beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 153 reviews
Top guest favourite
Earthen home in Bundanoon
The Artist's House, Bundanoon NSW
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Oct
4.96 out of 5 average rating, 329 reviews