Dempsey Hill Vacations from $316

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

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.
Habyt Clarke Quay - Previously Champion City

Habyt Clarke Quay - Previously Champion City

3.5 out of 5
Downtown Singapore
Price was $425, price is now $316 per person
$316
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.2/10 Very Good! (608 reviews)
Clean and functional, Premium room has a lovely view on the park. For that price, a great deal.

Reviewed on May 26, 2026

One Farrer Hotel

One Farrer Hotel

5 out of 5
Rochor
Price was $646, price is now $450 per person
$450
per person
Sep 7 - Sep 10
found 24 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9.2/10 Wonderful! (1,001 reviews)
Room waa clean and good. I got free upgrade. Thanks to the friendly staff.

Reviewed on Jun 1, 2026

Goodwood Park Hotel

Goodwood Park Hotel

4.5 out of 5
Orchard
Price was $634, price is now $470 per person
$470
per person
Aug 4 - Aug 6
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9/10 Wonderful! (1,002 reviews)
I think the Goodwood is a hidden Gem in an oasis of its own on the hill. Grand building with dedicated staff. We love it .

Reviewed on Jun 27, 2026

Homix Hotel

Homix Hotel

2.5 out of 5
Novena
Price was $536, price is now $424 per person
$424
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
No reviews
Aurum Royal

Aurum Royal

3 out of 5
Downtown Singapore
Price was $545, price is now $433 per person
$433
per person
Sep 7 - Sep 10
found 24 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9/10 Wonderful! (20 reviews)
Great property with lots of shops and restaurants close by, and next to a metro station. Staff were very helpful when we came in early and the nice noon checkout was appreciated

Reviewed on Jun 17, 2026

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
82% of travellers recommend
Singapore: Gardens by the Bay Admission E-Ticket
Singapore River Cruise

Singapore River Cruise E-Ticket

$23
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
$104 nightly
The price is $113 total per night from Jun 28 to Jun 29
$113 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (1,822 reviews)
"The hotel is conveniently located and nice overall. However, there was no hot water in the faucet and some of the electric fixtures were quite flimsy."

Reviewed on Jun 25, 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
$340 nightly
The price is $371 total per night from Jul 1 to Jul 2
$371 total
Jul 1 - Jul 2
Total with taxes and fees
9.4/10 Exceptional! (2,175 reviews)
"TJ is one of your best employees hands down!!!! He is the one by the door, goes out of his way to serve and deliver. Please thank him for us. It was clean location was perfect, the cleaning was on point, the music at night was such a welcome gesture and I am so grateful that the 1st time I come to ..."

Reviewed on Jun 25, 2026

Pan Pacific Singapore
Swissotel The Stamford, Singapore

Swissotel The Stamford, Singapore

5 out of 5
2 Stamford Road Singapore
Fully refundableReserve now, pay when you stay
$271 nightly
The price is $296 total per night from Jul 5 to Jul 6
$296 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"Lovely hotel with great pool area. Worth noting that we were required to upgrade our reservation in order to receive an early check in, which we were fine with. Also, some confusion as to whether the pool could be used post check out (we were told both yes and no). Other than that, the rooms were ..."

Reviewed on Jun 25, 2026

Swissotel The Stamford, Singapore
See all 784 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 $316 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.