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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.
View Sydney

View Sydney

4 out of 5
North Sydney
Price was $3,253, price is now $1,670 per person
$1,670
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a terrace, and a picnic area are also offered.
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Price was $3,568, price is now $1,757 per person
$1,757
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)
This aparthotel features an indoor pool and a gym. Traveling on business? Take advantage of the express check-out and WiFi in public areas. A hot tub is on site, while self parking and concierge services are also offered.
InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Price was $3,904, price is now $1,963 per person
$1,963
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Serene Studio With Balcony in Prime Location

Serene Studio With Balcony in Prime Location

2.5 out of 5
Wollstonecraft
Price was $3,275, price is now $1,674 per person
$1,674
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)
Stylish Studio in the Heart of Vibrant Surry Hills

Stylish Studio in the Heart of Vibrant Surry Hills

2 out of 5
Surry Hills
Price was $3,315, price is now $1,699 per person
$1,699
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Sydney (SYD)

Top Wingecarribee Shire Council hotels deals

Berrima Bakehouse Motel

Berrima Bakehouse Motel

3.5 out of 5
19 Old Hume Highway Berrima NSW
$99 nightly
The price is $109 total per night
$109 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
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
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
$133 nightly
The price is $146 total per night
$146 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
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
The Imperial Motel

The Imperial Motel

4 out of 5
Cnr Bong Bong & Bundaroo Sts Bowral NSW
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $122 total per night
$122 total
Dec 22 - Dec 23
Total with taxes and fees
This smoke-free motel features 2 restaurants and 3 bars/lounges. Guests will appreciate free perks like free self parking and WiFi in public areas. Luggage storage is also provided.
Parking included
Free WiFi
Berida Hotel

Berida Hotel

4 out of 5
6 David Street Bowral NSW
Free Cancellation
Reserve now, pay when you stay
$138 nightly
The price is $152 total per night
$152 total
Dec 23 - Dec 24
Total with taxes and fees
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
Links House

Links House

4 out of 5
17 Links Road Burradoo NSW
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $141 total per night
$141 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
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
Bundanoon Hotel

Bundanoon Hotel

3 out of 5
6-18 Erith Street Bundanoon NSW
Free Cancellation
Reserve now, pay when you stay
$82 nightly
The price is $90 total per night
$90 total
Dec 22 - Dec 23
Total with taxes and fees
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
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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.

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Wingecarribee Shire Council
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