Dempsey Hill Holidays

Photo by Michael Lee
  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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

Things to do in and around Dempsey Hill

Dempsey Hill is an ideal destination for city-themed, family, and business vacations, offering a variety of activities. Visitors can enjoy leisurely strolls through charming shopping areas, including a shopping mall centre and various boutique shops. This vibrant locale combines relaxation with the excitement of retail therapy, making it a perfect spot for both casual explorers and dedicated shoppers.

Shopping

Dempsey Hill offers a unique shopping experience with Lotto Carpets Gallery right in the area. Nearby, ION Orchard is just 1.6km away, featuring vibrant entertainment and family-friendly vibes. The Paragon, located 3.2km away, also promises a delightful shopping atmosphere with a mix of stores and dining options.

Recreation

Mount Faber Park offers a peaceful retreat with its lush greenery and panoramic views, perfect for relaxation and leisurely strolls. Singapore Island Country Club provides a luxurious environment for wellness activities, while Singapore Cricket Club combines sport and leisure, ideal for those seeking active recreation in a vibrant atmosphere.

Adventure

Experience breathtaking views from the Singapore Cable Car, a thrilling gondola ride offering outdoor family fun. For a scenic hike, the Singapore Botanic Gardens Loop provides stunning landscapes, while the Nepenthes Trail invites you to explore the rich flora in a peaceful outdoor setting.

Nightlife

Dempsey Hill offers a vibrant nightlife with cultural experiences at Singapore Repertory Theatre and Drama Box, both just a short distance away. For those seeking thrills, the GX-5 Xtreme Swing provides an adventurous ride, making for an exciting evening filled with entertainment and family-friendly vibes.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Dempsey Hill

Dempsey Hill offers a delightful blend of urban charm, family-friendly activities, and cultural experiences. Visitors can explore the serene urban parks, delve into the fascinating exhibits at local history museums, and visit beautiful temples. This area caters to those seeking a vibrant city atmosphere, enriching family experiences, and a touch of history, making it a perfect destination for tourists looking to embrace both leisure and culture in Singapore.

  • Orchard Road: Experience the bustling energy of Orchard Road, a vibrant shopping street brimming with luxury boutiques, department stores, and a plethora of dining options. It's the perfect destination for those seeking the latest fashion trends and a taste of Singapore's urban lifestyle.
  • Singapore Botanic Gardens: Immerse yourself in the tranquillity of the Singapore Botanic Gardens, a UNESCO World Heritage Site. With lush greenery, beautiful landscapes, and romantic spots, it’s a delightful place for families and couples to enjoy leisurely strolls amidst nature.
  • National University of Singapore: Explore the historic campus of the National University of Singapore, renowned for its rich cultural heritage and academic excellence. The striking architecture and serene surroundings offer a glimpse into the scholarly life and history of Singapore.

Best time to go to Dempsey Hill

The best time to visit Dempsey Hill is dependent on what kind of holiday you are seeking. May is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with moderate rain. January is its coolest month on average. At this time, visitor numbers are slightly high and weather is mostly cloudy with moderate rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January79.7°F (26.5°C)Moderate RainMostly CloudySlightly HighAverage
February80.2°F (26.8°C)Light RainMostly SunnyAverageAverage
March81.3°F (27.4°C)Moderate RainMostly SunnyAverageSlightly Low
April82.6°F (28.1°C)Moderate RainMostly CloudySlightly LowAverage
May83.3°F (28.5°C)Moderate RainMostly CloudySlightly LowSlightly Low
June82.9°F (28.3°C)Moderate RainMostly CloudySlightly LowSlightly Low
July82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly High
August82.2°F (27.9°C)Moderate RainMostly CloudyAverageAverage
September82.0°F (27.8°C)Light RainMostly SunnySlightly HighSlightly High
October82.2°F (27.9°C)Moderate RainMostly CloudyAverageAverage
November81.3°F (27.4°C)Frequent RainMostly CloudyAverageAverage
December80.2°F (26.8°C)Frequent RainMostly CloudySlightly HighSlightly High

Booking tips and Expedia advantages for Dempsey Hill

To save money on your visit to Dempsey Hill, consider travelling during the cheaper months of March and May to June, and aim for Saturday stays, which are the least expensive. Enjoy free attractions like the Singapore Botanic Gardens and Fort Canning Park. For public transport, cycling is an economical option. Book your accommodation about a month in advance for the best rates, and explore last-minute deals on Expedia for additional savings. Combining hotel bookings with flights can also lead to significant discounts.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Dempsey Hill are March and May to June, where the prices are slightly lower. This is in comparison to July, September and December, where prices are slightly higher.
  • The best time to book a hotel: Booking a hotel in Dempsey Hill about 1 month out from when you are planning to stay is usually when prices are lowest. If you're a little more spontaneous, you could also peruse Expedia's last minute deals for hotels, look out for the green banner below the price, as this indicates a cheaper deal.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Dempsey Hill is Saturday. The most expensive day to stay in Dempsey Hill is Thursday.
  • Find cheap hotels on Expedia: Expedia’s search tool enables you to specify your budget and preferred location, among other options. You can arrange your search results to display prices from lowest to highest, ensuring you see the most affordable hotels first. Additionally, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can enjoy significant savings by combining your Dempsey Hill hotel reservation with your flights and activities through an Expedia package.

Top hotels in Dempsey Hill

Carlton Hotel Singapore

Carlton Hotel Singapore

4.5 out of 5
76 Bras Basah Road, Singapore
The price is S$262 per night from 9 Nov to 10 Nov
S$262
9 Nov - 10 Nov
includes taxes & fees
9/10 Wonderful! (2,004 reviews)
Very clean rooms. Excellent stay with professional ,courteous and helping staff . Rooms were well spaced and a excellent bed for a comfortable to rest.

Reviewed on 29 Oct, 2025

Carlton Hotel Singapore
Pan Pacific Singapore

Pan Pacific Singapore

5 out of 5
7 Raffles Boulevard, Marina Square, Singapore
Fully refundableReserve now, pay when you stay
The price is S$384 per night from 15 Nov to 16 Nov
S$384
15 Nov - 16 Nov
includes taxes & fees
9.2/10 Wonderful! (1,751 reviews)
The staff were extremely courteous throughout. We especially had fabulous service in the lounge those were Xuan, Myatt, Elin and Steve. Breakfast was brilliant lots of choice and all of course served with champagne should you want it !

Reviewed on 30 Oct, 2025

Pan Pacific Singapore
Crowne Plaza Changi Airport by IHG

Crowne Plaza Changi Airport by IHG

5 out of 5
75 Airport Boulevard, Singapore
Fully refundable
The price is S$339 per night from 2 Dec to 3 Dec
S$339
2 Dec - 3 Dec
includes taxes & fees
9.2/10 Wonderful! (2,224 reviews)
Friendly staff on check in. There was a problem with the room and Josiah Gwee was excellent in dealing with the problem. Very much appreciated the complimentary dinner in the Allore restaurant as an apology. All good. I would stay at the Crowne Plaza again.

Reviewed on 29 Oct, 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.

Popular places to visit

What to do in Dempsey Hill

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.