Dempsey Hill Vacations from $460

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.
CUBE Boutique Capsule Hotel @ Chinatown

CUBE Boutique Capsule Hotel @ Chinatown

2 out of 5
Downtown Singapore
Price was $645, price is now $460 per person
$460
per person
Aug 31 - Sep 7
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.2/10 Very Good! (268 reviews)
This is more like a hostel than a hotel. There’s limited floor space in the room (we had to keep our checked luggage outside the room) while we were in the room. The bathrooms were clean and all individual units which was more than expected. There’s also no elevator in the “hotel”. Although the staff was willing to help bring luggage up the stairs as needed. There was a water fill station in reception which was great and the “hotel” is right in the heart of Chinatown so the location is great! Overall was had a good stay - just a bit more cramped than expected.

Reviewed on Mar 24, 2026

Hmlet Kada at Maxwell

Hmlet Kada at Maxwell

4 out of 5
Downtown Singapore
Save 100% on your flight
Price was $978, price is now $524 per person
$524
per person
Aug 31 - Sep 7
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.4/10 Very Good! (16 reviews)
Great location close to food centre. Rooms are a bit old

Reviewed on Apr 24, 2026

Hmlet Cantonment

Hmlet Cantonment

3.5 out of 5
Tanjong Pagar
Save 100% on your flight
Price was $768, price is now $501 per person
$501
per person
Aug 31 - Sep 7
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.8/10 Excellent! (233 reviews)
Convenient access to any transportation - MRT or busses. Place is quiet, bed is comfortable,room was small but it has everything I need. Staff was courteous especially Jonathan. I will stay here again on my next trip to Singapore.

Reviewed on May 30, 2026

CUBE Family Boutique Capsule Hotel

CUBE Family Boutique Capsule Hotel

2.5 out of 5
Downtown Singapore
Save 100% on your flight
Price was $836, price is now $558 per person
$558
per person
Aug 31 - Sep 7
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

Le Grove Serviced Residences

Le Grove Serviced Residences

3.5 out of 5
Tanglin
Save 100% on your flight
Price was $926, price is now $649 per person
$649
per person
Aug 31 - Sep 7
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.8/10 Excellent! (377 reviews)
Staff and rooms were nice but breakfast buffet was very stingy and low rent…..quite disappointing….felt like staff were “guarding” the limited food available

Reviewed on Jan 24, 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

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 Jun 21 to Jun 22
$342 total
Jun 21 - Jun 22
Total with taxes and fees
9.4/10 Exceptional! (2,162 reviews)
"Good stay but hosuekeeping needs to improve. Staff very helpful and cordial"

Reviewed on Jun 15, 2026

Pan Pacific Singapore
Hotel Waterloo Singapore - Handwritten Collection

Hotel Waterloo Singapore - Handwritten Collection

4 out of 5
78 Waterloo Street Singapore
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $173 total per night from Jul 5 to Jul 6
$173 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (154 reviews)
"Great hotel. Close to many attractions. Rooms are very small but have everything."

Reviewed on Jun 15, 2026

Hotel Waterloo Singapore - Handwritten Collection
Paradox Singapore Merchant Court at Clarke Quay

Paradox Singapore Merchant Court at Clarke Quay

4.5 out of 5
Merchant Road, 20 Singapore SIN
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $206 total per night from Jun 28 to Jun 29
$206 total
Jun 28 - Jun 29
Total with taxes and fees
9.2/10 Wonderful! (1,495 reviews)
"Beautiful and clean property"

Reviewed on Jun 17, 2026

Paradox Singapore Merchant Court at Clarke Quay
See all 777 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 $460 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.