Pleasure Point Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Pleasure Point

Price found within the past 48 hours. Click for updated prices.
Sunny Apartment in Quiet and Green Neighbourhood

Sunny Apartment in Quiet and Green Neighbourhood

Lane Cove
CA $2,325
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
No reviews
Stylish Inner City 2-bed Unit by Fig Lane Park

Stylish Inner City 2-bed Unit by Fig Lane Park

Ultimo
CA $3,060
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Sydney (SYD)
No reviews
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

Sydney Central Business District
CA $2,566
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Sydney (SYD)
8.4/10 Very good! (1,002 reviews)
Silverwater Stay Near Parks and Cafes

Silverwater Stay Near Parks and Cafes

Silverwater
CA $2,655
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
No reviews
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District
CA $2,630
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
8.2/10 Very good! (2,903 reviews)
Stayed here before and they are still maintaining their excellent standards. Very well located right beside darling harbour. Enjoyed the free upgrade to the penthouse. Much appreciated.

Reviewed on Sep 5, 2026

Where to stay in Pleasure Point

Find the best Pleasure Point areas and neighborhoods for the activities you enjoy most. Learn more about Pleasure Point
A historic clock tower with a modern skyscraper in the background.

Sydney Central Business District

2 out of top 10 points of interest in this area

Historical and commercial heart of Sydney, the CBD boasts towering skyscrapers, lively café culture, and nightlife in areas like Darling Harbour. Explore parks such as Hyde Park and cultural institutions, while enjoying easy access to public transport.

Find hotels in Sydney Central Business District
A nighttime cityscape with illuminated buildings reflecting on the water.

Darling Harbour

Adjacent to Sydney's city centre, Darling Harbour boasts a pedestrian precinct with attractions like the Australian National Maritime Museum and Chinese Garden of Friendship. Enjoy dining at Cockle Bay Wharf, explore Tumbalong Park, and access various transport options, including the Inner West Light Rail and ferry services.

Find hotels in Darling Harbour
A large, arched building with multiple entry points, including signs for 'Entry' and 'No entry'.

Sydney Olympic Park

2 out of top 10 points of interest in this area

Featuring a large sports and entertainment area, commercial developments, and extensive parklands, this Greater Western Sydney suburb offers attractions like Bicentennial Park and Newington Armory. Easily accessible via Olympic Park railway line and ferry services.

Find hotels in Sydney Olympic Park
A crowded beach with people sunbathing and swimming, surrounded by buildings and trees.

Manly

Beach-side suburb with easy ferry access, Manly offers a mix of ocean and harbor beaches, scenic cycle tracks, and a lively commercial area along The Corso. Explore historic sites like North Head Quarantine Station and enjoy outdoor dining.

Find hotels in Manly
A street with vintage buildings, pedestrians, and parked cars.

The Rocks

1 out of top 10 points of interest in this area

Historic area near Sydney's city center, The Rocks boasts close proximity to Circular Quay and Harbour Bridge views. Explore weekend Rocks Market, galleries, and historic pubs like Fortune of War, while enjoying walkable streets and easy rail access.

Find hotels in The Rocks

Pleasure Point Hotel Deals

Shangri-La Sydney

Shangri-La Sydney

176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
CA $304
CA $334 total
Sep 6 - Sep 7
includes taxes & fees
9.2/10 Wonderful! (2,840 reviews)
"Really friendly and helpful staff. Spacious rooms. Clean with great amenities."

Reviewed on Sep 5, 2026

Shangri-La Sydney
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

252 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
CA $141
CA $155 total
Sep 20 - Sep 21
includes taxes & fees
8.2/10 Very good! (2,913 reviews)
"Stayed here before and they are still maintaining their excellent standards. Very well located right beside darling harbour. Enjoyed the free upgrade to the penthouse. Much appreciated."

Reviewed on Sep 5, 2026

YEHS Hotel Sydney Harbour Suites
Hyatt Regency Sydney

Hyatt Regency Sydney

161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
CA $244
CA $268 total
Sep 20 - Sep 21
includes taxes & fees
Hyatt Regency Sydney
See all 5,662 properties in Pleasure Point
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Frequently asked questions

How much does a Pleasure Point vacation package cost?
Live it up in Pleasure Point from as little as CA $2,325. We offer a wonderful selection of hotels, flights and rental cars to suit every budget. You can score even better deals when you add a couple of sightseeing tours to your package.
How do I get a cheap travel package to Pleasure Point?
Lock in flights that suit your schedule, add a hotel room to your booking and watch the savings stack up with a Pleasure Point vacation package. It's as simple as that! From hotels and flights to rental cars and tours, Expedia is your gateway to cheap travel. And with more than 550 airlines and 1,000,000 properties throughout the world to select from, you'll never be short of choice.
Where should I stay in Pleasure Point?
If you're eager to be in the middle of the action, stay near Sydney Showground. Many visitors book a hotel around this top attraction.
How far in advance should I book my Pleasure Point vacation?
To bag rock-bottom prices, book ASAP. Airlines typically advertise flights, along with some of the lowest fares, around 12 months in advance. Hotels, activities and car rental should also be booked well in advance so you can have the pick of the bunch. If you're in need of a last-minute getaway in Pleasure Point, there are always lots of great deals on Expedia. Check them out now!
What does an Expedia Pleasure Point travel package include?
Flights, rental cars and hotels, or any combination of the three — the choice is yours. Whether you're visiting Pleasure Point with the entire family or traveling solo, there's a bundle to suit every style and budget. Once you've made your booking, why not add on a few tours or activities?
What should I know before booking a Pleasure Point travel package?
Whether it's relaxation or adventure you're craving, a Pleasure Point vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Pleasure Point Expedia vacation package?
With a vacation package, you're in control. Whether you want to fly to Pleasure Point in coach or business class, simply pick from the available airline options. Expedia has access to more than 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Pleasure Point vacation package?
You sure can, and we'll help you every step of the way. You may be able to amend or cancel your Pleasure Point vacation package at no cost within 24 hours of booking. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If life throws you a curveball, look up our Customer Service Portal for more information.

Things to do

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

CA $51
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Sydney Opera House Official Guided Walking Tour

Sydney Opera House Official Guided Walking Tour

CA $49
per adult
96% of travellers recommend
Sydney Opera House Official Guided Walking Tour
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

CA $28
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
See all activities in Sydney
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.