Dempsey Hill Vacations from $377

Book a Hotel + Flight or Car together to unlock savings

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.
Homix Hotel

Homix Hotel

2.5 out of 5
Novena
Price was $532, price is now $377 per person
$377
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
No reviews

Hotel Bencoolen@Hong Kong Street

Hotel Bencoolen@Hong Kong Street

4 out of 5
Downtown Singapore
Save 100% on your flight
Price was $664, price is now $393 per person
$393
per person
Oct 4 - Oct 7
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

A Hotel Joo Chiat

A Hotel Joo Chiat

2.5 out of 5
Geylang
Price was $701, price is now $503 per person
$503
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7.8/10 Good! (57 reviews)
Room is clean. Aircon and heater are working well

Reviewed on Jul 7, 2026

Aurum Royal

Aurum Royal

3 out of 5
Downtown Singapore
Price was $586, price is now $450 per person
$450
per person
Sep 7 - Sep 10
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 Bus Collective

The Bus Collective

3 out of 5
Changi
Save 100% on your flight
Price was $1,168, price is now $901 per person
$901
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.2/10 Very Good! (34 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Dempsey Hill
View all trips

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
$139 nightly
The price is $152 total per night from Aug 5 to Aug 6
$152 total
Aug 5 - Aug 6
Total with taxes and fees
8.8/10 Excellent! (1,838 reviews)
"The hotel was good for a central location, but is hidden away behind several other buildings. I am not fond of the self checkin at any hotel, especially when everyone can see your details on the large screens. Finding your way around from the hotel is difficult. Where you are dropped off is not on ..."

Reviewed on Jul 11, 2026

YOTEL Singapore Orchard Road
Swissotel The Stamford, Singapore

Swissotel The Stamford, Singapore

5 out of 5
2 Stamford Road Singapore
Fully refundableReserve now, pay when you stay
$299 nightly
The price is $326 total per night from Aug 3 to Aug 4
$326 total
Aug 3 - Aug 4
Total with taxes and fees
9.4/10 Exceptional! (1,021 reviews)
"Filter water fountain was at the room. Just need a water bottle."

Reviewed on Jul 11, 2026

Swissotel The Stamford, Singapore
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! (2,180 reviews)
"Great hotel - our choice whenever we are in Singapore"

Reviewed on Jul 9, 2026

Pan Pacific 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Dempsey Hill vacation package cost?
Offering excellent value package deals from $377 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.

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.