Dempsey Hill Holidays

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Top hotels in Dempsey Hill

Pan Pacific Singapore

Pan Pacific Singapore

7 Raffles Boulevard Singapore
Fully refundableReserve now, pay when you stay
S$520
18 Sept - 19 Sept
includes taxes & fees
Pan Pacific Singapore
JEN Singapore Tanglin by Shangri-La

JEN Singapore Tanglin by Shangri-La

1A Cuscaden Road Singapore
Fully refundableReserve now, pay when you stay
S$240
19 Sept - 20 Sept
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Great location by the TEL mrt. Excellent service, very helpful staff, great breakfast. Highly recommend!"

Reviewed on 14 Sept, 2026

JEN Singapore Tanglin by Shangri-La
Hotel Boss

Hotel Boss

500 Jalan Sultan Road Singapore
Fully refundableReserve now, pay when you stay
S$136
12 Oct - 13 Oct
includes taxes & fees
7.8/10 Good! (1,303 reviews)
"Rooms were small, bed was like a rock. Really nice outdoor pool."

Reviewed on 15 Sept, 2026

Hotel Boss
See all 797 properties in Dempsey Hill
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.
See properties

What to do in Dempsey Hill

Singapore: Gardens by the Bay Admission E-Ticket

Singapore: Gardens by the Bay Admission E-Ticket

S$43
per adult
84% of travellers recommend
Singapore: Gardens by the Bay Admission E-Ticket
Gardens by the Bay

Singapore: Gardens by the Bay Entry Ticket

S$10
per adult
90% of travellers recommend
Singapore: Gardens by the Bay Entry Ticket
Singapore Night Safari E-Ticket

Night Safari Admission Ticket

S$61
per adult
86% of travellers recommend
Night Safari Admission Ticket
See all activities in Dempsey Hill

Frequently asked questions

How much does a Dempsey Hill holiday package cost?
Offering excellent value package deals 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?
  1. Pick your dates: What you'd like to do in Dempsey Hill and your favourite season can help you decide when to get away.
  2. 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.
  3. 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.
  4. Combine your accommodation and airfare: After you've nailed down your dates and duration, book the right Dempsey Hill holiday package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.