Dempsey Hill Vacations from $366

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Your Dempsey Hill Vacation

With plenty of highlights as well as hidden gems, this city is best experienced with a Dempsey Hill vacation package. Find somewhere to stay in East Coast, which is great for camping, shopping and families. Love to venture out and explore? Haji Lane, Chinatown Heritage Center and National Orchid Garden are among the leading places to visit during your trip to Dempsey Hill. Your Dempsey Hill vacation is just a few clicks away. Search hotels, flights and more on Expedia for an adventure that's tailored to suit your style.

The Latest Dempsey Hill vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Royal

Aurum Royal

3 out of 5
Downtown Singapore
Price was $521, price is now $366 per person
$366
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9/10 Wonderful! (23 reviews)
Full breakfast provided. Central location in Chinatown, easy to walk to attractions and restaurants. Hot tub was out of order during our stay. Ice was not available most nights. Bed was way too hard. Room was small. Good price.

Reviewed on Jul 5, 2026

The Fullerton Bay Hotel

The Fullerton Bay Hotel

5 out of 5
Marina Bay
Save 100% on your flight
Price was $1,433, price is now $896 per person
$896
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9.6/10 Exceptional! (769 reviews)
Fabulous room, we loved the pool area and breakfast was lovely with many choices. We can’t wait to return to the hotel and stay again. Disappointed we couldn’t get our loyalty recognised as we booked through Wotif and not with hotel directly but we got a great deal so can’t complain.

Reviewed on Jun 22, 2026

Hotel Bencoolen@Hong Kong Street

Hotel Bencoolen@Hong Kong Street

4 out of 5
Downtown Singapore
Price was $603, price is now $419 per person
$419
per person
Sep 28 - Sep 30
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.4/10 Very Good! (1,000 reviews)
Staff are nice, the place is very convenient.

Reviewed on Jul 1, 2026

COMO Metropolitan Singapore

COMO Metropolitan Singapore

5 out of 5
Orchard
Save 100% on your flight
Price was $1,098, price is now $812 per person
$812
per person
Sep 13 - Sep 17
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9.2/10 Wonderful! (110 reviews)
Convenient location and great pool.

Reviewed on Jun 27, 2026

five6 Hotel Splendour

five6 Hotel Splendour

3.5 out of 5
Geylang
Price was $537, price is now $400 per person
$400
per person
Sep 13 - Sep 17
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.4/10 Very Good! (842 reviews)

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Stay near popular Dempsey Hill attractions

Lotto Carpets Gallery

You can spend an afternoon exploring the galleries in Lotto Carpets Gallery in Dempsey Hill. Wander 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

$34
per adult
84% of travellers recommend
Singapore: Gardens by the Bay Admission E-Ticket
Singapore River Cruise

Singapore River Cruise E-Ticket

$22
per adult
82% of travellers recommend
Singapore River Cruise E-Ticket
Singapore Cable Car

Singapore: Sentosa Cable Car Sky Pass Roundtrip Ticket

$23
per adult
94% of travellers recommend
Singapore: Sentosa Cable Car Sky Pass Roundtrip Ticket
See all activities in Dempsey Hill

Dempsey Hill Hotel Deals

YOTEL Singapore Orchard Road

YOTEL Singapore Orchard Road

4 out of 5
366 Orchard Road Singapore
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $137 total per night from Aug 2 to Aug 3
$137 total
Aug 2 - Aug 3
Total with taxes and fees
8.8/10 Excellent! (1,830 reviews)
"This is a nice hotel with seamless check in and check out process. The staff are very nice and ensure the customer is comfortable. The hotel is at a great location, right next to an MRT station and the Ion Orchard Mall."

Reviewed on Jul 5, 2026

YOTEL Singapore Orchard Road
Pan Pacific Singapore

Pan Pacific Singapore

5 out of 5
7 Raffles Boulevard Singapore
Fully refundableReserve now, pay when you stay
$320 nightly
The price is $349 total per night from Aug 5 to Aug 6
$349 total
Aug 5 - Aug 6
Total with taxes and fees
9.4/10 Exceptional! (2,176 reviews)
"For a family trip, the prime location, delicious breakfast, and clean rooms were impressive. The Marina Bay view was also excellent."

Reviewed on Jul 5, 2026

Pan Pacific Singapore
Paradox Singapore

Paradox Singapore

4.5 out of 5
Merchant Road, 20 Singapore SIN
Fully refundableReserve now, pay when you stay
$217 nightly
The price is $238 total per night from Jul 31 to Aug 1
$238 total
Jul 31 - Aug 1
Total with taxes and fees
9.2/10 Wonderful! (1,525 reviews)
"The air condition of the room is not that cold. We complain and they sent a worker to reset the system and is was only a little better. If you want cold air condition please don't come to this hotel it will disappoint you. Also the front staff that check us in wasn't that friendly either."

Reviewed on Jul 6, 2026

Paradox Singapore
See all 790 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.

Find the Best Dempsey Hill Vacation Packages

Dempsey Hill Essential Information

Language
Malaysian
Currency
Singapore dollars
Local Goodbye
Sampai jumpa lagi
Closest Airport
Changi Airport (SIN)
Max Temp Winter
85ºF
Max Temp Summer
90ºF
Top Sights
Universal Studios Singapore, Singapore Zoo and East Coast Park

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Frequently asked questions

How much does a Dempsey Hill vacation package cost?
Offering excellent value package deals from $366 on Expedia, you'll be surprised at how little a vacation 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?
You can generally find lower prices and better availability in November, December and January. Browse our cheap Dempsey Hill vacation packages and you could land some great off-season deals.
How many days is enough for Dempsey Hill?
Typically, a handful of days is enough to tick off the main sights during your Dempsey Hill vacation. However, if you'd like to have some time to kick back or take day tours, think about extending your itinerary.
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 vacation as a package?
Expedia vacation 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 vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation 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. Choose when to travel: Check your diary and get packing. Your favorite time of year and the type of activities available will also help you decide when to escape to Dempsey Hill.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and meals to experiences and flights. Your hotel will probably be the biggest expense during your trip to Dempsey Hill.
  3. Explore Dempsey Hill using our trip planning tool: Gain insights into the top attractions and best stays for your trip to Dempsey Hill. You can also save your favorite places, collaborate with your group and organize all your plans in one place.
  4. Decide your trip length: Think about how much time you want to spend exploring Dempsey Hill. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Dempsey Hill vacation package.
  6. Add on experiences and excursions: Read our dedicated travel guide to find some incredible things to do in Dempsey Hill. Book tickets or make reservations as soon as you can to save time and avoid the stress of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Dempsey Hill vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Dempsey Hill trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.