Dempsey Hill Vacation Packages

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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.

Top Dempsey Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Bugis Social- Newly Renovated

Bugis Social- Newly Renovated

3 out of 5
Bugis Village
Price was CA $529, price is now CA $430 per person
CA $430
per person
Sep 23 - Sep 26
found 17 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8/10 Very good! (6 reviews)
Bathrooms have no soap Staff won't give spare Keycards (Need to share 1 among many guests) Not soundproof Have to speak Chinese to the staff who work the graveyard shift

Reviewed on Jul 1, 2026

Grand Park City Hall

Grand Park City Hall

5 out of 5
Downtown Singapore
Price was CA $946, price is now CA $654 per person
CA $654
per person
Sep 2 - Sep 5
found 18 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9/10 Wonderful! (1,269 reviews)
Breakfast was less than average, same food every day, not a large choice. Always out of plates, cups, food. It's a poor set up part of the food in one area some in another. The tables were unorganized.

Reviewed on Jul 15, 2026

five6 Hotel Splendour

five6 Hotel Splendour

3.5 out of 5
Geylang
Price was CA $596, price is now CA $453 per person
CA $453
per person
Sep 3 - Sep 6
found 17 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
8.4/10 Very good! (842 reviews)

Carlton City Hotel Singapore

Carlton City Hotel Singapore

5 out of 5
Downtown Singapore
Price was CA $854, price is now CA $684 per person
CA $684
per person
Sep 23 - Sep 26
found 17 hours ago
Roundtrip flight included
Manila (MNL) to Singapore (SIN)
9.4/10 Exceptional! (2,172 reviews)
Room was of a high standard and bedding, mattress and pillows of high quality. Pool & gym were very good. Staff very helpful and hotel in a good location.

Reviewed on Jul 15, 2026

Hotel Bencoolen@Hong Kong Street

Hotel Bencoolen@Hong Kong Street

4 out of 5
Downtown Singapore
Price was CA $4,023, price is now CA $2,771 per person
CA $2,771
per person
Aug 17 - Aug 22
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Singapore (SIN)
8.4/10 Very good! (1,000 reviews)
Staff are nice, the place is very convenient.

Reviewed on Jul 1, 2026

Ready to book your vacation to Dempsey Hill?

 

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Dempsey Hill Hotel Deals

YOTEL Singapore Orchard Road

YOTEL Singapore Orchard Road

4 out of 5
366 Orchard Road Singapore
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Aug 2 to Aug 3
CA $185
CA $222 total
Aug 2 - Aug 3
includes taxes & fees
8.8/10 Excellent! (1,829 reviews)
"Good location to shopping district near Orchard and Scott's roads. The largest room was still a bit small for 3 people. The lifts are a bit annoying. Press a button and there is an immediate noise and light for an elevator but that does not mean it is coming soon. Decent buffet offerings with egg ..."

Reviewed on Jul 15, 2026

YOTEL Singapore Orchard Road
Swissotel The Stamford, Singapore

Swissotel The Stamford, Singapore

5 out of 5
2 Stamford Road Singapore
Fully refundableReserve now, pay when you stay
The price is CA $467 per night from Aug 10 to Aug 11
CA $467
CA $560 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,016 reviews)
"The Executive rooms on the high level floors are very good. Great view but you pay for it! However the L65 lounge access for breakfast was very nice and family friendly too. The hotel is probably the best location in Singapore for sightseeing. Easy to get a grab taxi - about $12 to sentosa. Plenty ..."

Reviewed on Jul 15, 2026

Swissotel The Stamford, Singapore
Pan Pacific Singapore

Pan Pacific Singapore

5 out of 5
7 Raffles Boulevard Singapore
Fully refundableReserve now, pay when you stay
The price is CA $461 per night from Jul 30 to Jul 31
CA $461
CA $552 total
Jul 30 - Jul 31
includes taxes & fees
9.4/10 Exceptional! (2,187 reviews)
"Hotel is quite dated and our rooms had wiring issues (aircon and lights) and the staff had to call the technician 4 times over our 5 night stay. The pool while big was not very clean. The elevators can take up to 10 minutes. On the plus side their is a kids play area and the buffet breakfast is ..."

Reviewed on Jul 13, 2026

Pan Pacific Singapore
See all 791 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.
All Inclusive Vacations
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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

CA $48
per adult
84% of travellers recommend
Singapore: Gardens by the Bay Admission E-Ticket
Singapore River Cruise

Singapore River Cruise E-Ticket

CA $32
per adult
82% of travellers recommend
Singapore River Cruise E-Ticket
Universal Studios Singapore Admission Ticket

Universal Studios Singapore Admission Ticket

CA $59
per adult
Universal Studios Singapore Admission Ticket
See all activities in Dempsey Hill

Frequently asked questions

How much does a Dempsey Hill vacation package cost?
You can pick up a vacation package to this destination from CA $430 on Expedia. But how much your vacation to Dempsey Hill costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Dempsey Hill?
You can typically find lower prices and better availability in January, February and June. Check out our cheap Dempsey Hill vacation packages and you could land some great off-season deals.
How many days is enough for Dempsey Hill?
Dedicate at least 4 days for your Dempsey Hill vacation if you're hoping to enjoy everything that makes this place unique. Wander around popular neighbourhoods, including Downtown Singapore and Downtown Core. Then tick off major sights such as Marina Bay Sands Casino and Marina Bay Sands Skypark. With a clever itinerary, you can keep busy with room for some rest and relaxation too. Want to venture outside of Dempsey Hill? Consider fitting in a day trip or two.
How to find the best Dempsey Hill package deals?
Start your search for a Dempsey Hill package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Dempsey Hill package deal right away, simply play around with your dates and search again. Remember 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?
You can enjoy significant savings on your next Dempsey Hill break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Dempsey Hill?
If you have your Dempsey Hill travel dates locked in, book as early as you can to snap up some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Dempsey Hill?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to escape to Dempsey Hill.
  2. Budget wisely: As well as the price of your accommodations, you should factor in other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Dempsey Hill.
  3. Decide your trip length: Think about how long you want to spend discovering Dempsey Hill. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the right Dempsey Hill vacation package for you.

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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.