Dempsey Hill Holidays from NZ$2,633
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The Latest Dempsey Hill Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Bencoolen@Hong Kong Street
Downtown Singapore
NZ$2,711
per person
2 Oct - 4 Oct
found 6 hours ago
Return direct flight included
Auckland (AKL) to Singapore (SIN)
8.4/10 Very good! (1,002 reviews)
Did not like anything other than the quick check in and central location.Tiny room, tiny outdated bathroom, stained carpets in the corridors, dont even bother with breakfast. It will be an ok place if you only sleep in the room.
Reviewed on 10 Aug 2026
Dao by Dorsett AMTD Singapore
Marina Bay
NZ$2,717
per person
2 Oct - 4 Oct
found 6 hours ago
Return direct flight included
Auckland (AKL) to Singapore (SIN)
9.4/10 Exceptional! (761 reviews)
Staff were helpful, solo traveler and they gave me an upgrade. Close to great shopping and food, and nice walk along the marina bay.
Room was amazing
Reviewed on 8 Aug 2026
Dempsey Hill Holiday
Our pick of the best Dempsey Hill Hotel Deals
Swissotel The Stamford, Singapore
2 Stamford Road Singapore
Fully refundableReserve now, pay when you stay
NZ$524
1 Sept - 2 Sept
includes taxes & fees
9.4/10 Exceptional! (1,043 reviews)
"Really hope that there was complimentary parking. We had to repark our car which was a 15min walk away. Food was ok We felt that more could be done for the service"
Reviewed on 10 Aug 2026
Pan Pacific Singapore
7 Raffles Boulevard Singapore
Fully refundableReserve now, pay when you stay
NZ$586
29 Aug - 30 Aug
includes taxes & fees
9.4/10 Exceptional! (2,214 reviews)
"Second time staying and excellent as usual"
Reviewed on 11 Aug 2026
Hotel Boss
500 Jalan Sultan Road Singapore
Fully refundableReserve now, pay when you stay
NZ$174
3 Sept - 4 Sept
includes taxes & fees
7.8/10 Good! (1,282 reviews)
"Family-friendly"
Reviewed on 11 Aug 2026
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.
Stay near popular Dempsey Hill attractions
Lotto Carpets Gallery
You can spend an afternoon studying the exhibits at Lotto Carpets Gallery in Dempsey Hill. Wander through the picturesque gardens and marina in this vibrant area.
What to do in Dempsey Hill
Singapore: Gardens by the Bay Admission E-Ticket
NZ$57
per adult
84% of travellers recommend
Singapore Hop-On Hop-Off Bus Tour by Open-Top Bus
NZ$85
per adult
84% of travellers recommend
Frequently asked questions
How much does a Dempsey Hill holiday package cost?
Offering excellent value package deals from NZ$2,633 on Expedia, you'll be surprised at how little a holiday to Dempsey Hill costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Dempsey Hill?
If you'd like to book a cheap Dempsey Hill holiday package, consider travelling in January, February and June. You're likely to find better rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Dempsey Hill?
With a well-organised schedule, you can easily visit the most popular Dempsey Hill sights in a few days. But if you want to explore off the beaten track or go on day trips, consider booking your Dempsey Hill holiday for longer.
How to find the best Dempsey Hill package deals?
Start your search for a Dempsey Hill package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Dempsey Hill package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Dempsey Hill getaway off to a flying start.
Is it cheaper to book a Dempsey Hill holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still have the freedom to create a tailored Dempsey Hill holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Dempsey Hill?
If you're considering an impromptu Dempsey Hill getaway, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Dempsey Hill?
- Pick your dates: What you'd like to do in Dempsey Hill and your favourite season can help you decide when to get away.
- Plan your budget wisely: Besides the cost of your stay, you should consider other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may arise during your trip to Dempsey Hill.
- Work out your trip length: Think about how much time you want to spend exploring Dempsey Hill. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
- Combine your accommodation and airfare: After you've nailed down your dates and duration, book the right Dempsey Hill holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
