Dempsey Hill Vacations from $439

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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.
Hotel 1900 @ Chinatown

Hotel 1900 @ Chinatown

4 out of 5
Downtown Singapore
Save 100% on your flight
Price was $706, price is now $439 per person
$439
per person
Jul 26 - Jul 29
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.8/10 Excellent! (180 reviews)
Very clean, staffs were very professional and friendly. Hope had more outlets for charging stations; also don’t like the water draining system in shower which floods the toilet areas every time use the shower.

Reviewed on May 11, 2026

Hmlet Kada at Maxwell

Hmlet Kada at Maxwell

4 out of 5
Downtown Singapore
Save 100% on your flight
Price was $829, price is now $451 per person
$451
per person
Sep 1 - 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

Hotel Bencoolen@Hong Kong Street

Hotel Bencoolen@Hong Kong Street

4 out of 5
Downtown Singapore
Save 100% on your flight
Price was $922, price is now $547 per person
$547
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.4/10 Very Good! (1,000 reviews)
Clean room and awesome staff

Reviewed on Jun 11, 2026

Oasia Residence Singapore

Oasia Residence Singapore

3.5 out of 5
Clementi
Save 100% on your flight
Price was $975, price is now $635 per person
$635
per person
Aug 31 - Sep 7
found 22 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9.4/10 Exceptional! (45 reviews)
very clean and professional staff

Reviewed on Apr 22, 2026

Habyt Cantonment (formerly Hmlet Cantonment)

Habyt Cantonment (formerly Hmlet Cantonment)

3.5 out of 5
Bukit Merah
Save 100% on your flight
Price was $675, price is now $442 per person
$442
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.8/10 Excellent! (230 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

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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
$316 nightly
The price is $344 total per night from Jun 19 to Jun 20
$344 total
Jun 19 - Jun 20
Total with taxes and fees
9.4/10 Exceptional! (2,180 reviews)
"Good stay but hosuekeeping needs to improve. Staff very helpful and cordial"

Reviewed on Jun 15, 2026

Pan Pacific Singapore
Carlton Hotel Singapore

Carlton Hotel Singapore

4.5 out of 5
76 Bras Basah Road Singapore
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Jun 26 to Jun 27
$168 total
Jun 26 - Jun 27
Total with taxes and fees
9.2/10 Wonderful! (2,613 reviews)
"Stayed here for 2 days. Hotel was very clean , upscale. Rooms were big and comfortable. The location is excellent, walking distance to Clarke quay, marina bay and shops and dining. Would stay here again"

Reviewed on Jun 15, 2026

Carlton Hotel Singapore
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
$151 nightly
The price is $167 total per night from Jun 19 to Jun 20
$167 total
Jun 19 - Jun 20
Total with taxes and fees
9.2/10 Wonderful! (1,513 reviews)
"Property seemed a little tired. Shower head and lack of hot water was an issue, but was fixed promptly when we brought it to thier attention. Lighting in the room insufficient, especially for older people with poorer eye sight. Also, it was the 1st hotel in our 4 weeks of travel not to have a TV ..."

Reviewed on Jun 14, 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

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Frequently asked questions

How much does a Dempsey Hill vacation package cost?
Offering excellent value package deals from $439 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.