Dempsey Hill Vacations from $364

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.
Owen House by Habyt

Owen House by Habyt

3 out of 5
Rochor
Price was $507, price is now $364 per person
$364
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.6/10 Excellent! (319 reviews)
The hotel looks aesthetic and new but this is deceiving. The beds are not comfy and the bathroom has a weird smell (like sewage) coming from the drains. The cleaning service is every 3 days which is poor since you need to request replacements for towels and TP via WhatsApp (and sometimes requests are not replied to in a reasonable time) - at times the front desk is also unmanned. The facilities in the room are poorly designed: only 3 plugs (out of 5) worked and once the "main switch" for lights is turned off at night no outlets work (so you can't charge phones overnight). The coffee and food in the cafe downstairs is poor too: the coffee and food at other places nearby is better. The only positive I can think to add is this hotel is close to MRT lines, a shopping mall and near to a variety of restaurants (South Asian, East Asian, Turkish food etc).

Reviewed on Jul 7, 2026

A Hotel Bugis

A Hotel Bugis

3 out of 5
Downtown Core
Save 100% on your flight
Price was $966, price is now $600 per person
$600
per person
Oct 5 - Oct 9
found 1 hour ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7.4/10 Good! (106 reviews)
Close to Bugis Street

Reviewed on Jul 3, 2026

CUBE Family Boutique Capsule Hotel

CUBE Family Boutique Capsule Hotel

2.5 out of 5
Downtown Singapore
Price was $539, price is now $376 per person
$376
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7/10 Good! (144 reviews)
Location location location. Nicely centralized in Chinatown. Easy access to the MRT. Walking reachable to Newton Food Center. Little bit more to Lau Pa Sat too.

Reviewed on May 6, 2026

Homix Hotel

Homix Hotel

2.5 out of 5
Novena
Price was $533, price is now $378 per person
$378
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
No reviews

METT Singapore

METT Singapore

5 out of 5
Downtown Singapore
Save 100% on your flight
Price was $777, price is now $554 per person
$554
per person
Sep 7 - Sep 10
found 23 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9.6/10 Exceptional! (41 reviews)
Such a sweet hotel which is in a gorgeous and peaceful spot but very conveniently located for all of Singapore. Staff are so helpful, great beds and enjoyed the pools. The gym is fantastic but not easy to find first time round! Thanks for a great stay.

Reviewed on Jun 22, 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
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
$153 nightly
The price is $167 total per night from Aug 2 to Aug 3
$167 total
Aug 2 - Aug 3
Total with taxes and fees
8.8/10 Excellent! (1,840 reviews)
"staff helpful and kind. close to main orchard amd full of options for restaurants bar and shopping"

Reviewed on Jul 13, 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
$292 nightly
The price is $319 total per night from Aug 3 to Aug 4
$319 total
Aug 3 - Aug 4
Total with taxes and fees
9.4/10 Exceptional! (1,023 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
$327 nightly
The price is $357 total per night from Aug 10 to Aug 11
$357 total
Aug 10 - Aug 11
Total with taxes and fees
9.4/10 Exceptional! (2,185 reviews)
"I stayed 2 nights at the Marina Bay Sands and was apprehensive about the next hotel. I needn't have been. The Pan Pacific was wonderful experience. Food was good, staff was very helpful and the room was beautiful!! I would absolutely stay there again!!"

Reviewed on Jul 12, 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 $364 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.