Dempsey Hill Vacations from ￥108,475

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The Latest Dempsey Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Oasia Residence Singapore

Oasia Residence Singapore

3.5 out of 5
Clementi
Save 100% on your flight
Price was ￥161,194, price is now ￥108,475 per person
￥108,475
per person
Sep 23 - Sep 29
found 23 hours ago
Roundtrip flight included
Tokyo (TYO) to Singapore (SIN)
9.4/10 Exceptional! (45 reviews)
very clean and professional staff

Reviewed on Apr 22, 2026

Hmlet Kada at Maxwell

Hmlet Kada at Maxwell

4 out of 5
Downtown Singapore
Save 100% on your flight
Price was ￥190,466, price is now ￥115,924 per person
￥115,924
per person
Sep 11 - Sep 18
found 21 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Singapore (SIN)
8.4/10 Very Good! (16 reviews)

Liv Residences Serviced Apartment Novena

Liv Residences Serviced Apartment Novena

4 out of 5
Novena
Price was ￥214,260, price is now ￥149,500 per person
￥149,500
per person
Sep 11 - Sep 18
found 21 hours ago
Roundtrip non-stop flight included
Osaka (KIX) 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

Carlton Hotel Singapore

Carlton Hotel Singapore

4.5 out of 5
Downtown Core
Price was ￥206,804, price is now ￥146,560 per person
￥146,560
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Singapore (SIN)
9.2/10 Wonderful! (2,628 reviews)
A fantastic hotel walking distance to public transport and sightseeing. Across the road from Raffles shopping centre where there were many food options. Our room was upgraded and we enjoyed an earlier than expected check in which we were so grateful especially after our 13 hr flight. Buffet breakfast offered good variety, housekeeping excellent, reception staff polite and helpful. The pool was so welcoming after a hot day wandering around this amazing city. We used taxi to & from airport $29 each way which made everything easy. Highly recommend !

Reviewed on Jul 8, 2026

The Fullerton Bay Hotel

The Fullerton Bay Hotel

5 out of 5
Marina Bay
Price was ￥286,740, price is now ￥206,084 per person
￥206,084
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Singapore (SIN)
9.6/10 Exceptional! (769 reviews)
Fabulous room, we loved the pool area and breakfast was lovely with many choices. We can’t wait to return to the hotel and stay again. Disappointed we couldn’t get our loyalty recognised as we booked through Wotif and not with hotel directly but we got a great deal so can’t complain.

Reviewed on Jun 22, 2026

Find the Best Dempsey Hill Vacation Packages

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 ￥20,557 per night from Aug 5 to Aug 6
￥20,557
￥24,648 total
Aug 5 - Aug 6
includes taxes & fees
8.8/10 Excellent! (1,831 reviews)
"This is a nice hotel with seamless check in and check out process. The staff are very nice and ensure the customer is comfortable. The hotel is at a great location, right next to an MRT station and the Ion Orchard Mall."

Reviewed on Jul 5, 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 ￥49,256 per night from Aug 4 to Aug 5
￥49,256
￥59,058 total
Aug 4 - Aug 5
includes taxes & fees
9.4/10 Exceptional! (2,178 reviews)
"For a family trip, the prime location, delicious breakfast, and clean rooms were impressive. The Marina Bay view was also excellent."

Reviewed on Jul 5, 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 ￥31,719 per night from Aug 1 to Aug 2
￥31,719
￥38,785 total
Aug 1 - Aug 2
includes taxes & fees
9.2/10 Wonderful! (1,529 reviews)
"Very clean room, reasonably priced, great pool and gym"

Reviewed on Jul 8, 2026

Paradox Singapore
See all 790 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.

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

￥5,473
per adult
82% of travellers recommend
Singapore: Gardens by the Bay Admission E-Ticket
Singapore Night Safari E-Ticket

Night Safari Admission Ticket

￥7,624
per adult
90% of travellers recommend
Night Safari Admission Ticket
Singapore River Cruise

Singapore River Cruise E-Ticket

￥3,632
per adult
82% of travellers recommend
Singapore River Cruise E-Ticket
See all activities in Dempsey Hill

Frequently asked questions

How much does a Dempsey Hill vacation package cost?
Offering excellent value package deals from ￥108,475 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?
If you'd like to book a cheap Dempsey Hill vacation package, consider traveling in January, February and June. You're likely to find better rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Dempsey Hill?
With a well-organized schedule, you can easily visit the most popular Dempsey Hill sights in a few days. But if you want to explore off the beaten track or go on day trips, consider booking your Dempsey Hill vacation for longer.
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. Pick your dates: What you'd like to do in Dempsey Hill and your favorite season can help you decide when to get away.
  2. Plan your budget wisely: Besides the cost of your stay, you should consider other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may arise during your trip to Dempsey Hill.
  3. Work out your trip length: Think about how much time you want to spend exploring Dempsey Hill. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your accommodations and airfare: After you've nailed down your 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.