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.
Hmlet Kada at Maxwell

Hmlet Kada at Maxwell

4 out of 5
Downtown Singapore
Price was CA $3,284, price is now CA $2,685 per person
CA $2,685
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Singapore (SIN)
8.4/10 Very good! (16 reviews)

One Farrer Hotel

One Farrer Hotel

5 out of 5
Rochor
Price was CA $3,719, price is now CA $3,003 per person
CA $3,003
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Singapore (SIN)
9.2/10 Wonderful! (1,000 reviews)
Wonderful staff (Naren) who looked after us well after a long journey to singapore. Upgraded room was even amazing.

Reviewed on Jun 24, 2026

Liv Residences Serviced Apartment Novena

Liv Residences Serviced Apartment Novena

4 out of 5
Novena
Price was CA $3,696, price is now CA $2,989 per person
CA $2,989
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Singapore (SIN)
9.8/10 Exceptional! (6 reviews)
Pleasant friendly staff, generous with bottled water for our daily needs, clean accommodation and pool, free self service laundry services… what’s not to like 😊

Reviewed on Jun 9, 2026

ONE15 Marina Hotel Sentosa Cove

ONE15 Marina Hotel Sentosa Cove

4 out of 5
Sentosa Island
Price was CA $3,550, price is now CA $2,965 per person
CA $2,965
per person
Aug 3 - Aug 7
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Singapore (SIN)
8.4/10 Very good! (343 reviews)

ANDAZ SINGAPORE, BY HYATT

ANDAZ SINGAPORE, BY HYATT

5 out of 5
Bugis Village
Price was CA $3,987, price is now CA $3,388 per person
CA $3,388
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Singapore (SIN)
9.2/10 Wonderful! (1,003 reviews)
Terrible

Reviewed on Jun 27, 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 $167 per night from Jul 30 to Jul 31
CA $167
CA $200 total
Jul 30 - Jul 31
includes taxes & fees
8.8/10 Excellent! (1,819 reviews)
"Hôtel en bonne condition et situé à moins de 10 mins à pied du Métro (MRT) station Orchard. Copieux buffet déjeuner. Chambres propres mais petites."

Reviewed on Jun 30, 2026

YOTEL Singapore Orchard Road
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 $439 per night from Jul 28 to Jul 29
CA $439
CA $526 total
Jul 28 - Jul 29
includes taxes & fees
9.4/10 Exceptional! (2,179 reviews)
"Lovely staff with super nice and clean room!"

Reviewed on Jun 30, 2026

Pan Pacific Singapore
Paradox Singapore

Paradox Singapore

4.5 out of 5
Merchant Road, 20 Singapore SIN
Fully refundableReserve now, pay when you stay
The price is CA $275 per night from Jul 24 to Jul 25
CA $275
CA $337 total
Jul 24 - Jul 25
includes taxes & fees
9.2/10 Wonderful! (1,518 reviews)
"Great location 10/10 right across from a shopping centre, Starbucks, food court and MRT. Hotel is everything you need although a little dated and the lifts need some love but we really enjoyed our stay. Breakfast has a huge selection. Great hotels if you have small kids."

Reviewed on Jul 1, 2026

Paradox Singapore
See all 785 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 $47
per adult
82% of travellers recommend
Singapore: Gardens by the Bay Admission E-Ticket
Singapore River Cruise

Singapore River Cruise E-Ticket

CA $31
per adult
82% of travellers recommend
Singapore River Cruise E-Ticket
Universal Studios Singapore Admission Ticket

Universal Studios Singapore Admission Ticket

CA $92
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 $2,685 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.