
Dempsey Hill Vacations from ¥103,544
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Dempsey Hill Vacation Packages
Price found within the past 48 hours. Click for updated prices.


Jyu Capsule Hotel
Downtown Singapore
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Singapore (SIN)
9/10 Wonderful! (85 reviews)
As a solo female traveller, I found the property safe and very clean. The staff was very helpful, and I would staff here again.
Reviewed on Jun 7, 2025

Habyt Kada at Maxwell
Downtown Singapore
Save 100% on your flight
per person
Oct 6 - Oct 12
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Singapore (SIN)
7.8/10 Good! (6 reviews)
The room size and equipment were great, but it's ridiculous that there isn't a SINGLE hook anywhere to hang your towel, shirt, or pants.
I had to pick up cheap suction hooks from Daiso, so I had places to hang items that were frequently used. Sure the wardrobe has a bunch of hangers but you don't want to stuff your used day-pants in there. Makes no sense.
The room cleaning only happens on Wednesdays, so you'll also need a hook to hold your garbage in a separate plastic bag. The garbage bin in the room is just too small for a week's worth of trash.
Walls are thin, you'll hear your neighbors or room mates talk on their phone, and all the activity in the shared living space - this was esp apparent when my neighbor was cooking, doing laundry, inviting her friends over, etc.
The 100 year old, very slow lift is cool the first time... but a real pain in the ass to use. You have to pull open two very heavy metal gates, and pull to close them (and ensure they're very closed) before you can hit the button to go up or down. Usually by midnight the lift will stop working... because the bargoers that use the lift forget to close the gates after they've gone to the top floor. And when new guests come in or out, everyone is very confused who should be helping to open or close the inner/outer gates. It's a nightmare when you're a regular guest and all you want to do is just enter or exit the hotel on the 3rd floor. Often, just waiting for the lift takes forever - if it comes at all.
Reviewed on May 8, 2025

Find the Best Dempsey Hill Vacation Packages
Dempsey Hill Hotel Deals

Carlton Hotel Singapore
76 Bras Basah Road, Singapore
Fully refundableReserve now, pay when you stay
The price is ¥20,662 per night from Aug 25 to Aug 26
¥20,662
¥25,739 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (1,774 reviews)
"위치가 너무 좋아서 접근성이 매우 훌륭함"
Reviewed on Jul 29, 2025

Paradox Singapore Merchant Court at Clarke Quay
Merchant Road, 20, Singapore, SIN
Fully refundableReserve now, pay when you stay
The price is ¥27,602 per night from Aug 30 to Aug 31
¥27,602
¥33,094 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (1,206 reviews)
"Had a fantastic stay with Paradox Singapore Merchant Clarke Quay. Great location, with easy access to restaurants, bars, shopping & the trains. Staff & service were excellent, and the little touches of fruit infused iced water in the lobby after a long day in the heat, made it even more enjoyable. ..."
Reviewed on Jul 28, 2025

Crowne Plaza Changi Airport by IHG
75 Airport Boulevard, Singapore
The price is ¥33,599 per night from Aug 27 to Aug 28
¥33,599
¥40,285 total
Aug 27 - Aug 28
includes taxes & fees
9.2/10 Wonderful! (2,151 reviews)
"We specifically booked this hotel so that we could access the facilities and attractions based at Singapore Airport and because we had an early morning flight."
Reviewed on Aug 2, 2025
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.
Discover the most popular places to visit in Dempsey Hill

Universal Studios Singapore
4.5/5(322 reviews)
Enjoy the thrills at Universal Studios Singapore and see why everyone loves this amusement park in Singapore. Amble around this vibrant area's marina and enjoy its top-notch restaurants.

Marina Bay Sands Casino
4.5/5(390 reviews)
Why not try your luck with a visit to Marina Bay Sands Casino where you can enjoy the games and entertainment of this top casino in Singapore? Amble within picturesque gardens or visit the shops in this vibrant area.

Orchard Road
4.5/5(752 reviews)
Spend the day shopping for the world’s biggest brands at one of the most popular shopping destinations in Asia.
What to do in Dempsey Hill

Singapore: Gardens by the Bay Admission E-Ticket
¥2,736
per adult
74% of travellers recommend

Singapore Highlights & Hidden Gems: Private Tour with Local Host
¥22,624
per traveler
100% of travellers recommend

Universal Studios Singapore Admission Tickets + Express Day Pass
¥29,390
per adult
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.