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Hewn out of the living rock in the 1860s using hand tools and blasting powder, Big Hill Cutting was at one time the deepest railway cutting in the southern hemisphere. Taken as it was near the eastern end of the cutting, even this pic doesn't properly illustrate the depth. The cutting has a long and macabre history, with several workers killed during its construction due to a blasting accident and several drivers later perishing after crashing their automobiles through the old timber bridge's guardrails and down onto the rails below. Despite the history, it's a peaceful and beautiful place. The old railway line was abandoned in the 1970s and runs for around 50km between the towns of Thirlmere and Mittagong. Although not a proper rail trail, there are service trails parallelling the railway for much of its length. I've walked it a few times, including the trip pictured which was undertaken 2-Boot-Drive Swagman style ;-)

Mittagong

Vacations
Mittagong
Ye Old Bicycle shoppe in Bundanoon. You can rent bicycles and they can give you some good information on where to go. They also have a café attached. The building just looks really cool.

Bundanoon

Vacations
Bundanoon

Wingecarribee Shire Council flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Haven Glebe

Haven Glebe

4.5 out of 5
Glebe
Price was $1,858, price is now $1,308 per person
$1,308
per person
Apr 28 - May 2
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Sydney (SYD)
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Price was $3,113, price is now $2,466 per person
$2,466
per person
Mar 26 - Mar 31
found 2 days ago
Roundtrip flight included
San Francisco (SFO) to Sydney (SYD)
This luxury hotel includes 3 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and airport shuttle. Enjoy the a rooftop terrace and unwind at the bar/lounge and poolside bar.
APX World Square

APX World Square

4.5 out of 5
Haymarket
Price was $1,853, price is now $1,508 per person
$1,508
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
This aparthotel features an outdoor pool and a gym. WiFi in public areas is free. Self parking, dry cleaning, and luggage storage are also offered.
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Price was $1,546, price is now $1,342 per person
$1,342
per person
Mar 25 - Mar 27
found 15 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Sydney (SYD)
Free WiFi in public areas, express check-out, and luggage storage are available at this hotel. A safe deposit box is also provided.
Mariners Court Hotel Sydney

Mariners Court Hotel Sydney

3.5 out of 5
Woolloomooloo
Price was $1,519, price is now $1,324 per person
$1,324
per person
Apr 28 - May 2
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Sydney (SYD)
This motel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Business travelers can take advantage of the business center. A restaurant, a terrace, and a garden are also provided.

Top Wingecarribee Shire Council hotels deals

Park Proxi Gibraltar Bowral

Park Proxi Gibraltar Bowral

4 out of 5
Boronia Street (off Centennial Road) Bowral NSW
Free Cancellation
Reserve now, pay when you stay
The price is $173 total per night
$173 total
per night
Feb 15 - Feb 16
A golf course and a gym are featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.
Parking included
Free WiFi
Berrima Bakehouse Motel

Berrima Bakehouse Motel

3.5 out of 5
19 Old Hume Highway Berrima NSW
The price is $119 total per night
$119 total
per night
Feb 15 - Feb 16
Free WiFi in public areas, a garden, and a picnic area are available at this motel. Express check-out and barbecue grills are also provided.
Free WiFi
Air conditioning
The Robertson Hotel

The Robertson Hotel

3.5 out of 5
1 Fountaindale Rd Robertson NSW
The price is $117 total per night
$117 total
per night
Mar 9 - Mar 10
An outdoor pool is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.
Pool
Parking included
Berida Hotel

Berida Hotel

4 out of 5
6 David Street Bowral NSW
Free Cancellation
Reserve now, pay when you stay
The price is $156 total per night
$156 total
per night
Feb 23 - Feb 24
This guesthouse features a restaurant and 2 bars/lounges. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A terrace, a garden, and a snack bar/deli are also on offer.
Parking included
Free WiFi
Bundanoon Hotel

Bundanoon Hotel

3 out of 5
6-18 Erith Street Bundanoon NSW
Free Cancellation
Reserve now, pay when you stay
The price is $96 total per night
$96 total
per night
Mar 3 - Mar 4
This hotel features a restaurant, an outdoor tennis court, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden is also provided.
Parking included
Free WiFi
Links House

Links House

4 out of 5
17 Links Road Burradoo NSW
Free Cancellation
Reserve now, pay when you stay
The price is $156 total per night
$156 total
per night
Mar 10 - Mar 11
A restaurant and a bar/lounge are featured at this guesthouse. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A business center, a garden, and a snack bar/deli are also on offer.
Breakfast included
Pet friendly
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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.

Photos of local treasures

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Bradman Oval is situated at Bowral in the southern highlands area of New South Wales, Australia. It was named after cricketer Don Bradman, who lived locally and played at the ground in the 1920s. His ashes are scattered on and near the Oval
Bradman Oval is situated at Bowral in the southern highlands area of New South Wales, Australia. It was named after cricketer Don Bradman, who lived locally and played at the ground in the 1920s. His ashes are scattered on and near the Oval
. He suggested Carrington Falls, just 20 minutes away, as a better option. Disappointed, but somehow grateful, I did a U-turn and headed off. I’d been here before, but now had a better camera, my Samsung S10 phone. These days I rarely use my accumulated Nikon gear, saving it for telephoto and night shots only. I hadn’t fitted flowers into my calculations, but there they were, flexing their leaves to the tune of the falling rain. Only one other couple were present and they were 300 metres in front. I had it basically all to myself. There’s something fulfilling about being surrounded by nature in all its forms. Droplets of water assembled on the leaves, bushes flushed with flowers and lovely even light
Follow an unmarked track for 30 minutes through the bush, watch out for snakes and fallen trees, and end up at this secluded swimming hole! #trovember
Following the "unofficial" track down to the base of the top falls brings you to this secluded swimming spot. #nature #localsecrets

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