Plan your trip
Photo by Michael Lee
Check prices for these dates, December 15 – 16, 2026
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.
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dempsey Hill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dempsey Hill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Whenever you want to travel, a warm welcome awaits you in Dempsey Hill. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Dempsey Hill in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $83 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
At Expedia, we put the best Dempsey Hill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Dempsey Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dempsey Hill vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dempsey Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Yes, we have vacation rentals where you'll be just 3.6 mi (5.8 km) from Universal Studios Singapore, offering you a secluded option if you want a quieter place to stay. Dempsey Hill is known for its gardens and shopping. Make sure you have time to check out the restaurants and football games during your trip.
While exploring the area, visit family-friendly sights like Universal Studios Singapore, or get outside and enjoy nature at National Orchid Garden. In the larger area, you’ll find popular places like Orchard Road and Marina Bay Sands Casino.
Vacation rentals are private properties where you can stay for a few weeks or just a few days in Dempsey Hill. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.