Dempsey Hill Vacations from $377

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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.
Hmlet Essentials Clarke Quay

Hmlet Essentials Clarke Quay

3.5 out of 5
Downtown Singapore
Price was $481, price is now $377 per person
$377
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.2/10 Very Good! (633 reviews)
It was a great experience it was close to the river and easy enough to walk to attractions and clean and comfortable room

Reviewed on Oct 28, 2026

Homix Hotel

Homix Hotel

2.5 out of 5
Central Singapore
Price was $561, price is now $384 per person
$384
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8/10 Very Good! (2 reviews)
Property is very small . Staff is good . Too small the dormitories are

Reviewed on Nov 3, 2026

A Hotel Farrer Park - Newly Renovated

A Hotel Farrer Park - Newly Renovated

3 out of 5
Little India
Price was $601, price is now $448 per person
$448
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7.2/10 Good! (72 reviews)
A

Reviewed on Nov 11, 2026

Hotel Grand Central

Hotel Grand Central

4 out of 5
Orchard
Price was $660, price is now $506 per person
$506
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7.4/10 Good! (856 reviews)
Hotel Grand Central Orchard Rd was not what I expected. This hotel does not have an actual lobby and looks dated and in need of an upgrade. Staff was very friendly and helpful though. Our room was a decent size but out bathroom was small and uncomfortable to take a shower in. We tried the paid breakfast and it was disappointing. There is a rooftop pool that we didn’t use, but it looked nice. The hotel if a bit far from the center, but there is a nearby subway station that would take you there in a few minutes.

Reviewed on Nov 2, 2026

Owen House by Hmlet

Owen House by Hmlet

3 out of 5
Central Singapore
Price was $507, price is now $396 per person
$396
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.4/10 Very Good! (360 reviews)
Room are pretty good space

Reviewed on Nov 6, 2026

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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

$33
per adult
86% of travellers recommend
Singapore: Gardens by the Bay Admission E-Ticket
Singapore River Cruise

Singapore River Cruise E-Ticket

$20
per adult
82% of travellers recommend
Singapore River Cruise E-Ticket
Singapore Gardens by the Bay Flower Dome Cloud Forest

Singapore Gardens by the Bay Flower Dome Cloud Forest

$32
per adult
86% of travellers recommend
Singapore Gardens by the Bay Flower Dome Cloud Forest
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
$329 nightly
The price is $358 total per night from Nov 21 to Nov 22
$358 total
Nov 21 - Nov 22
Total with taxes and fees
9.4/10 Exceptional! (2,364 reviews)
"We love the room and the robes were heavenly soft. The only complaint we have is the shower area. The water seeps out quite a lot if you use the shower heads that hit you middle part of the body…love that the restaurant downstairs offers local dishes :) will stay here again next time"

Reviewed on Nov 10, 2026

Pan Pacific Singapore
YOTEL Singapore Orchard Road

YOTEL Singapore Orchard Road

4 out of 5
366 Orchard Road Singapore
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $108 total per night from Nov 26 to Nov 27
$108 total
Nov 26 - Nov 27
Total with taxes and fees
8.8/10 Excellent! (1,817 reviews)
"Staff"

Reviewed on Nov 11, 2026

YOTEL Singapore Orchard Road
Hotel Boss

Hotel Boss

3.5 out of 5
500 Jalan Sultan Road Singapore
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $109 total per night from Nov 22 to Nov 23
$109 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (1,377 reviews)
"We enjoyed our one night stay at the Hotel Boss. It is well located within 10 minutes walk to Bugis Junction mall. Our room was clean but the downside is that it was quite small so storage for our two large suitcases and two small ones was abit challenging. The breakfast buffet was good with a decent ..."

Reviewed on Nov 10, 2026

Hotel Boss
See all 770 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 $377 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.