Dempsey Hill Vacations from $442

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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.
Four Chain View Hotel

Four Chain View Hotel

3 out of 5
Geylang
Price was $649, price is now $442 per person
$442
per person
Feb 1 - Feb 7
found 10 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
6.6/10 (185 reviews)

CUBE Family Boutique Capsule Hotel

CUBE Family Boutique Capsule Hotel

2.5 out of 5
Downtown Singapore
Price was $833, price is now $557 per person
$557
per person
Jan 14 - Jan 18
found 5 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7/10 Good! (153 reviews)

Hotel Mono

Hotel Mono

3 out of 5
Downtown Singapore
Price was $800, price is now $609 per person
$609
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.2/10 Very Good! (994 reviews)
Convenient, have a little window

Reviewed on Nov 9, 2026

Furama City Centre

Furama City Centre

4 out of 5
Downtown Singapore
Price was $630, price is now $505 per person
$505
per person
Feb 8 - Feb 11
found 1 day ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
7.8/10 Good! (1,444 reviews)
The location is excellent. The rooms are good size but could benefit from a refresh. Although the shower was hot and has good pressure you could not adjust the head so on full pressure it hit the back wall of the shower and leaked all over the floor. I do believe they were refreshing the rooms on my floor so unfortunately the last 2 nights of my stay my room smelled of paint? fumes or something. Perhaps they shouldn’t have people staying on the floor when they are working on the rooms.

Reviewed on Nov 13, 2026

Rest Rochor Hotel

Rest Rochor Hotel

3 out of 5
Little India
Price was $718, price is now $576 per person
$576
per person
Jan 6 - Jan 9
found 18 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9.6/10 Exceptional! (5 reviews)
Good location at a reasonable price.

Reviewed on Oct 7, 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
$327 nightly
The price is $357 total per night from Nov 21 to Nov 22
$357 total
Nov 21 - Nov 22
Total with taxes and fees
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
$110 nightly
The price is $120 total per night from Nov 15 to Nov 16
$120 total
Nov 15 - Nov 16
Total with taxes and fees
8.8/10 Excellent! (1,819 reviews)
"So far so good"

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! (1,380 reviews)
"Hotel Boss is in a great location. Lavender MRT is a short walk and the bus is right outside. There is a fabulous cafe serving amazing coffee just up the road, and superettes all around for bottled water and snacks. It is a busy hotel with lots of people coming and going all the time. It has a great ..."

Reviewed on Nov 12, 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 $442 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.