Dempsey Hill Vacations from $346

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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.
Jyu Capsule Hotel
Habyt Cantonment (formerly Hmlet Cantonment)
Habyt Kada at Maxwell
Orchard Point Serviced Apartments
ISA Hotel Amber Road
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Dempsey Hill Hotel Deals

Carlton Hotel Singapore

Carlton Hotel Singapore

4.5 out of 5
76 Bras Basah Road, Singapore
Fully refundableReserve now, pay when you stay
$173 nightly
The price is $189 total per night from Aug 29 to Aug 30
$189 total
Aug 29 - Aug 30
Total includes taxes and fees
9/10 Wonderful! (1,800 reviews)
"I had an excellent stay from check-in to check-out. The room was spacious, well-maintained, and impeccably clean, which made the experience very comfortable. Everything exceeded expectations. My only suggestion would be to make the bathroom a bit more accommodating for international guests by adding ..."

Reviewed on Aug 16, 2025

Carlton Hotel Singapore
Paradox Singapore Merchant Court at Clarke Quay

Paradox Singapore Merchant Court at Clarke Quay

4.5 out of 5
Merchant Road, 20, Singapore, SIN
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $216 total per night from Sep 17 to Sep 18
$216 total
Sep 17 - Sep 18
Total includes taxes and fees
9/10 Wonderful! (1,211 reviews)
"Hotel in fantastic location close to shopping, restaurants and MRT stop. Breakfast was amazing offering as was room service. Only disappointment, phone handset did not work and fridge not working. The latter we were told by maintenance was not there to cool but only to chill. It did neither nor did ..."

Reviewed on Aug 9, 2025

Paradox Singapore Merchant Court at Clarke Quay
Crowne Plaza Changi Airport by IHG

Crowne Plaza Changi Airport by IHG

5 out of 5
75 Airport Boulevard, Singapore
$236 nightly
The price is $257 total per night from Sep 8 to Sep 9
$257 total
Sep 8 - Sep 9
Total includes taxes and fees
9.2/10 Wonderful! (2,166 reviews)
Comfortable stay with little one.
"Our 4th or 5th times staying with Crown Ppaza Hotel. Love the location, the convenience and everything else. The room is new, everything is clean and nicely design. Friendly staff. Check-in a bit longer compare to some other hotel. Easy self-checkout. Would be even better if there is more luggage ..."

Reviewed on Aug 15, 2025

Crowne Plaza Changi Airport by IHG
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.

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Frequently asked questions

How much does a Dempsey Hill vacation package cost?
Offering excellent value package deals from $346 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.