Dempsey Hill Vacations from $369

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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.
Habyt Clarke Quay - Previously Champion City

Habyt Clarke Quay - Previously Champion City

3.5 out of 5
Downtown Singapore
Price was $456, price is now $369 per person
$369
per person
Aug 23 - Aug 26
found 22 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.2/10 Very Good! (603 reviews)
Clean and functional, Premium room has a lovely view on the park. For that price, a great deal.

Reviewed on May 26, 2026

Check-Inn at Little India

Check-Inn at Little India

3.5 out of 5
Little India
Save 100% on your flight
Price was $728, price is now $419 per person
$419
per person
Jul 23 - Jul 27
found 23 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7.4/10 Good! (433 reviews)
There were shops close by and the MRT was across the road. For the price, the place was OK. Rooms were tiny but tidy. Basic amenities and staff were very nice. Didn't know that they did not have elevators.

Reviewed on May 6, 2026

Amara Sanctuary Sentosa

Amara Sanctuary Sentosa

5 out of 5
Sentosa Island
Save 100% on your flight
Price was $1,511, price is now $1,086 per person
$1,086
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7.6/10 Good! (1,001 reviews)
Pros: Bed is clean, air con is silent and works well. The restaurant (Tearoom) served wonderful 5 stars food, including its breakfast. There is a shuttle bus from hotel to nearby and to Vivo city. Fast check in and check out. Cons: The hotel (for Premier room w balcony) need some facilities upgrading soon and to do a throughout cleaning. Room is generally dusty (seen from cups and parts of cabinets) and tile floor need proper mopping (the tiles had some chocolate stains from previous occupant which i had to clean), the cleaners were rushing to clean during peak hours. The basin and shower area wasn't clean properly. The shower water will wet the restroom as the glass door is not properly sealed. There are no space or equipment to hang multiple wet clothes and shower towels (poor design) Additional towel and toiletries requests (from room TV app) only came the next day afternoon.

Reviewed on Jun 8, 2026

Ascott Orchard Singapore

Ascott Orchard Singapore

5 out of 5
Orchard
Price was $1,214, price is now $991 per person
$991
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.8/10 Excellent! (383 reviews)
Rooms were very modern and clean. Staff very friendly and in a great location.

Reviewed on Apr 16, 2026

Resorts World Sentosa - Hotel Ora

Resorts World Sentosa - Hotel Ora

5 out of 5
Sentosa Island
Price was $1,546, price is now $1,303 per person
$1,303
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9/10 Wonderful! (250 reviews)
Great location. Rooms were big. Would have been good to have some outdoor furniture on balcony to enjoy the outdoor view, but all in all very great place to stay

Reviewed on May 25, 2026

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Discover the most popular places to visit in Dempsey Hill

Universal Studios Singapore

Universal Studios Singapore

Enjoy the thrills at Universal Studios Singapore and see why everyone loves this amusement park in Singapore. Amble around this vibrant area's marina and enjoy its top-notch restaurants.

Universal Studios Singapore
Orchard Road

Orchard Road

Spend the day shopping for the world’s biggest brands at one of the most popular shopping destinations in Asia.

Orchard Road
A nighttime cityscape with illuminated bridges and modern architecture.

Marina Bay Sands Skypark

Marina Bay Sands Skypark is just one of the places to see in Singapore, so why not enjoy the other things to explore during your travels? Amble within picturesque gardens or visit the shops in this vibrant area.

Marina Bay Sands Skypark

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
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)
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
$307 nightly
The price is $335 total per night from Jun 13 to Jun 14
$335 total
Jun 13 - Jun 14
Total with taxes and fees
9.4/10 Exceptional! (2,170 reviews)
"非常棒住宿体验，服务也是一流水平"

Reviewed on Jun 6, 2026

Pan Pacific 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
$196 nightly
The price is $215 total per night from Jul 1 to Jul 2
$215 total
Jul 1 - Jul 2
Total with taxes and fees
9.2/10 Wonderful! (1,501 reviews)
"Very clean and spacious room. Easy access to the MRT. We received a complimentary upgrade at check-in. We did not have an opportunity to enjoy the pool but are returning in just 2 days after a quick visit to Bintan and plan to spend the afternoon at the pool upon arrival."

Reviewed on Jun 9, 2026

Paradox Singapore Merchant Court at Clarke Quay
YOTEL Singapore Orchard Road

YOTEL Singapore Orchard Road

4 out of 5
366 Orchard Road Singapore
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $129 total per night from Jun 22 to Jun 23
$129 total
Jun 22 - Jun 23
Total with taxes and fees
8.8/10 Excellent! (1,831 reviews)
"Great hotel to stay while visiting Singapore! Especially for a couple. Very clean, organized and wonderful staff. The restaurant is very good, the buffet breakfast is amazing. Location is convenient to all the attractions, only short taxi service to most all locations. Will definitely be our first ..."

Reviewed on Jun 8, 2026

YOTEL Singapore Orchard Road
See all 774 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 $369 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.