Dempsey Hill Vacations from $471

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.
A Hotel Bugis

A Hotel Bugis

3 out of 5
Downtown Core
Save 100% on your flight
Price was $687, price is now $471 per person
$471
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7.4/10 Good! (110 reviews)
Close to Bugis Street

Reviewed on Jul 3, 2026

Hmlet Kada at Maxwell

Hmlet Kada at Maxwell

4 out of 5
Downtown Singapore
Save 100% on your flight
Price was $949, price is now $531 per person
$531
per person
Aug 31 - Sep 7
found 22 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.4/10 Very Good! (17 reviews)

Aurum Royal

Aurum Royal

3 out of 5
Downtown Singapore
Save 100% on your flight
Price was $1,219, price is now $756 per person
$756
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.6/10 Excellent! (30 reviews)
Thr hotel is located very close to a subway station, and a food Hawker. The hotel is simple, fair clean, room has what you can expect and suitable for my needs. The location is its best asset.

Reviewed on Jul 29, 2026

Hmlet Cantonment

Hmlet Cantonment

3.5 out of 5
Bukit Merah
Save 100% on your flight
Price was $739, price is now $504 per person
$504
per person
Aug 31 - Sep 7
found 22 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.8/10 Excellent! (239 reviews)
Clean room, tastefully furnished, communal kitchen, great work area and a pool on site.

Reviewed on Jul 14, 2026

Hotel Bencoolen@Hong Kong Street

Hotel Bencoolen@Hong Kong Street

4 out of 5
Downtown Singapore
Save 100% on your flight
Price was $842, price is now $587 per person
$587
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.4/10 Very Good! (1,004 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
Southern Albatross Adventure - Singapore Speedboat Thrills

Albatross Hop-On Hop-Off Speedboat Pass (1-Day Unlimited Speedboat Rides)

$31
per adult
Albatross Hop-On Hop-Off Speedboat Pass (1-Day Unlimited Speedboat Rides)
Gardens by the Bay

Singapore Gardens by the Bay

$8
per adult
90% of travellers recommend
Singapore Gardens by the Bay
See all activities in Dempsey Hill

Dempsey Hill Hotel Deals

Pan Pacific Singapore

Pan Pacific Singapore

5 out of 5
7 Raffles Boulevard Singapore
Fully refundableReserve now, pay when you stay
$314 nightly
The price is $342 total per night from Aug 26 to Aug 27
$342 total
Aug 26 - Aug 27
Total with taxes and fees
9.4/10 Exceptional! (2,205 reviews)
"The rooms were great and the staff were very friendly and helpful"

Reviewed on Jul 30, 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
$259 nightly
The price is $282 total per night from Aug 28 to Aug 29
$282 total
Aug 28 - Aug 29
Total with taxes and fees
9.4/10 Exceptional! (1,029 reviews)
"Very convenient location attached to the Raffles City Mall which made dining/shopping very easy. It’s also centrally located so you’re close to everything, including the train to & from Changi airport. Very happy with this beautiful hotel and will be back."

Reviewed on Jul 29, 2026

Swissotel The Stamford, Singapore
YOTEL Singapore Orchard Road

YOTEL Singapore Orchard Road

4 out of 5
366 Orchard Road Singapore
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $155 total per night from Aug 10 to Aug 11
$155 total
Aug 10 - Aug 11
Total with taxes and fees
8.8/10 Excellent! (1,829 reviews)
"The room was small like the picture, but it makes you feel cozy. I would highly recommend this hotel since it has so many accessible restaurants and malls nearby. Pretty good location with the given peice and hotel room."

Reviewed on Jul 30, 2026

YOTEL Singapore Orchard Road
See all 799 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 $471 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.