Holiday Homes in Southern Highlands

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Southern Highlands and around

Kendall’s Beach Cottage
Experience the charm of a coastal town with a scenic beachfront and picturesque views of the ocean.

Kendall’s Beach Cottage

10.0 out of 10, Exceptional, (90)
"Great place very close to the beach."
Kendall’s Beach Cottage
Cosy country stay in beautiful Berrima.
Property grounds

Cosy country stay in beautiful Berrima.

10.0 out of 10, Exceptional, (11)
Cosy country stay in beautiful Berrima.
Tranquil Retreat with Stunning Mountain and Country Views –Your Perfect Getaway!
Relax in this inviting living space with a comfortable sofa, armchair, and large window offering a garden view.

Tranquil Retreat with Stunning Mountain and Country Views –Your Perfect Getaway!

9.8 out of 10, Exceptional, (6)
"We loved our stay at the Jean House. The house is very spacious and the games room is amazing. Host was very responsive."
The price is €447
includes taxes & fees
13 Aug - 14 Aug
Tranquil Retreat with Stunning Mountain and Country Views –Your Perfect Getaway!
Secret Garden – Stay 3, Pay 2!
Enjoy serene views of the lush garden from the large windows in this peaceful room.

Secret Garden – Stay 3, Pay 2!

The price is €1,509
includes taxes & fees
11 Aug - 12 Aug
Secret Garden – Stay 3, Pay 2!
Casa Antica, 200m walk to Bowral Township, family and PET friendly UPON REQUEST
Enjoy cooking in this well-equipped kitchen with a gas stove, sink, and ample counter space.

Casa Antica, 200m walk to Bowral Township, family and PET friendly UPON REQUEST

8.6 out of 10, Excellent, (107)
"We had a wonderful stay in this beautiful home! Very central to town centre walking distance to everything! Would definitely recommend this place!"
Casa Antica, 200m walk to Bowral Township, family and PET friendly UPON REQUEST
The Boathouse/ Luxury Home/4mins walk Marina/Shops
Cozy living space with a dining table, sofa, and coffee table, perfect for relaxing and socializing.

The Boathouse/ Luxury Home/4mins walk Marina/Shops

10.0 out of 10, Exceptional, (24)
"A lovely property, everything spot on ! "
The Boathouse/ Luxury Home/4mins walk Marina/Shops
Iona Park, Moss Vale, Southern Highlands
Enjoy cooking in this well-equipped kitchen with a stove and ample counter space.

Iona Park, Moss Vale, Southern Highlands

9.0 out of 10, Wonderful, (2)
"We had a large group of friends staying at Iona Park for a reunion and we were all absolutely blown away. From the moment you arrive, the facilities are jaw dropping. Both the inside, especially the pool room and library, and outside (double tennis court!) were stunning. The kitchen was well stocked and plenty big enough to accommodate all of us. The check-in process was very smooth and the hosts were a pleasure to deal with. I can’t recommend this stay highly enough!"
Iona Park, Moss Vale, Southern Highlands
Luxury Heritage Cottage In The Heart Of Town
Sit and unwind in this serene outdoor seating area surrounded by lush greenery.

Luxury Heritage Cottage In The Heart Of Town

10.0 out of 10, Exceptional, (169)
"Perfect location and beautiful home. "
Luxury Heritage Cottage In The Heart Of Town
Aloha - Short Drive to Berry & The Beach - Fireplace and Firepit
Enjoy a serene beach experience with gentle waves lapping at the shore.

Aloha - Short Drive to Berry & The Beach - Fireplace and Firepit

8.6 out of 10, Excellent, (27)
"Good property close to the beach and all the sights of the region."
The price is €347
includes taxes & fees
19 Aug - 20 Aug
Aloha - Short Drive to Berry & The Beach - Fireplace and Firepit
Beautifully renovated Mountain cottage with Ocean view
Step into a charming outdoor space with a garden view, a wooden bench, and a vintage wagon wheel.

Beautifully renovated Mountain cottage with Ocean view

10.0 out of 10, Exceptional, (105)
"Great stay"
Beautifully renovated Mountain cottage with Ocean view
Twin Peaks - Kangaroo Valley
Relax in a serene garden setting with a deck, wicker chairs, and a small table.

Twin Peaks - Kangaroo Valley

10.0 out of 10, Exceptional, (5)
"Convenient location to village amenities and surrounding activities. Very clean and comfortable with excellent decor and furnishings. Perfect for weekend getaway."
Twin Peaks - Kangaroo Valley
The South Coasts Ultimate Luxury Beachfront - NEW LISTING
Relax on the deck with a serene view of the surrounding landscape, surrounded by comfortable seating and a glass railing.

The South Coasts Ultimate Luxury Beachfront - NEW LISTING

10.0 out of 10, Exceptional, (33)
"Excellent premium property with the best location on 7 mile beach"
The South Coasts Ultimate Luxury Beachfront - NEW LISTING
Beautiful Large Country Home in the Perfect Location with tennis court & theatre
Relax in a serene outdoor space with a palm tree, bench, and barbecue grill.

Beautiful Large Country Home in the Perfect Location with tennis court & theatre

10.0 out of 10, Exceptional, (20)
"Very nice accommodation, great hosts. Very easy to communicate with. We had a great weekend"
Beautiful Large Country Home in the Perfect Location with tennis court & theatre
Razorback Dream Farmhouse: 10BR, Space & Serenity
Surrounded by lush greenery and mature trees, this serene pool area offers a tranquil escape with a panoramic view of distant hills.

Razorback Dream Farmhouse: 10BR, Space & Serenity

8.2 out of 10, Very good, (38)
"Good for large group"
Razorback Dream Farmhouse: 10BR, Space & Serenity
Greenview Bowral Southern Highlands
Relax in a comfortable, contemporary space with a sofa, dining table, and outdoor seating area.

Greenview Bowral Southern Highlands

10.0 out of 10, Exceptional, (91)
"The entire process from booking to the actual stay was seamless. There was plenty of room for our 20 guests, the hosts have thought of everything and the property manager was excellent. It made our wedding weekend fabulous!"
Greenview Bowral Southern Highlands
Timbalah - a luxurious country retreat
Enjoy cooking in this well-equipped kitchen with a refrigerator, stove, and sink, plus ample storage space.

Timbalah - a luxurious country retreat

9.2 out of 10, Wonderful, (112)
"Good communication and flexibility from hosts to accomodate our group. "
Timbalah - a luxurious country retreat
Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima
Enjoy a serene view of the surrounding landscape from the balcony.

Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima

9.6 out of 10, Exceptional, (64)
"This was our fourth visit to Daphne Cottage. It was a terrific stay - the cottage is cosy and beautifully located and Phil, the owner, is excellent to deal with."
Daphne cottage - Heritage two storey 2 bedroom cottage in Historical Berrima
Beachfront House with direct access to the Beach. Just bring your beach towel!
Enjoy serene ocean views and stroll along the sandy beach.

Beachfront House with direct access to the Beach. Just bring your beach towel!

9.6 out of 10, Exceptional, (110)
"Location & view of the beach was perfect.Ten of us stayed & we were all very comfortable We had a fun few days together. Amanda was a great host- she was very easy to communicate with."
Beachfront House with direct access to the Beach. Just bring your beach towel!
Cabbage Tree Art House. $50 food & drinks voucher for all 3 night winter stays.
Enjoy a serene view of the lush garden from the large window, surrounded by a clean and minimalist design.

Cabbage Tree Art House. $50 food & drinks voucher for all 3 night winter stays.

10.0 out of 10, Exceptional, (1)
"Beautiful, clean and practical layout."
Cabbage Tree Art House. $50 food & drinks voucher for all 3 night winter stays.
Belle in Bowral - walk to town
Enjoy al fresco dining and social gatherings in this outdoor patio area with a dining table and comfortable seating.

Belle in Bowral - walk to town

9.8 out of 10, Exceptional, (54)
"Great location. Perfect accommodation for a Centennial Vineyard concert short stay."
The price is €291
includes taxes & fees
21 Aug - 22 Aug
Belle in Bowral - walk to town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southern Highlands Hotel Reviews

Nova Kiama

Nova Kiama

10/10 Excellent
" Great location . Pub next door with great food We loved that it was so clean . Staff were very helpfull . Shower pressure was great . "
Lisa 2-night trip
Posted 2 days ago
Nova Kiama