Dempsey Hill Holiday Rentals, Singapore: Private House Rentals

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Go beyond your typical stay in Dempsey Hill

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Our top choices for Dempsey Hill hotels

A bar area with a long counter, bar stools, and a bartender preparing drinks.

A lush indoor garden with a pathway leading to a seating area with wicker furniture and white cushions.

A modern bedroom with a large bed, a seating area with chairs, a television, and a view of greenery outside.

A serene outdoor pool area with a water feature, surrounded by lush greenery and modern seating.

1. Grand Hyatt Singapore

Orchard

Laurie

Rp5.313.770

Rp6.371.210 total

includes taxes & fees

16 Oct - 17 Oct

A tall hotel with a curved facade, illuminated signage, and a prominent 'Carlton' sign at the top.

An outdoor seating area with tables, chairs, and a sofa, surrounded by large potted plants and wooden slats.

A spacious lobby with a central seating area, a reception desk, and a decorative chandelier.

A hotel room with a large bed, a desk, a chair, a TV, a bathroom with a bathtub, and a view of the city.

2. Carlton Hotel Singapore

Central Singapore

Joseph Oluwafemi

Rp3.325.651

Rp3.987.456 total

includes taxes & fees

19 Oct - 20 Oct

A spacious lobby with a central water feature, surrounded by seating areas and large windows.

A modern building with a unique wooden lattice facade, surrounded by lush greenery and palm trees.

A multi-level atrium with balconies covered in greenery, a central open space, and a view of the sky.

A spacious lobby with high ceilings, large columns, and a central seating area with sofas and a small water feature.

3. Shangri-La Singapore

Central Singapore

Maria

Rp4.519.362

Rp5.418.715 total

includes taxes & fees

8 Nov - 9 Nov

A woman sitting by a large window with a city view, a vase with flowers, and a small table.

A rooftop lounge with a pool, outdoor seating, and large potted plants.

A spacious lobby with a fitness area, seating, and a large chandelier.

A modern dining area with a long table, cushioned seating, and potted plants.

4. Four Seasons Hotel Singapore

Orchard

MARISA

Rp6.182.060

Rp7.412.290 total

includes taxes & fees

13 Nov - 14 Nov

A spacious lobby with a grand staircase, a reception desk, and a decorative chandelier.

A buffet area with seafood, salads, and various dishes.

A modern hotel room with a living area, a dining table, a sofa, and a TV.

A swimming pool with colorful lounge chairs and a red building facade.

5. Royal Plaza on Scotts

Orchard

Kurt Wei

Rp3.408.504

Rp4.086.796 total

includes taxes & fees

18 Oct - 19 Oct

A modern hotel lobby with high ceilings, a central seating area, and a reception desk.

A modern hotel lobby with a central potted plant, geometric light fixtures, and a clean, minimalist design.

A modern hotel with a prominent Hilton sign, surrounded by high-rise buildings and a busy urban street at dusk.

6. Hilton Singapore Orchard

Orchard

Benjamin

Rp4.357.292

Rp5.224.393 total

includes taxes & fees

25 Oct - 26 Oct

A high-rise hotel with a prominent Grand Cypress sign, reflecting in the water.

A buffet with a variety of dishes and a scenic view through large windows.

A breakfast table with various dishes and drinks, a coffee pot, and a view of a cityscape through large windows.

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings and palm trees.

7. Grand Copthorne Waterfront Hotel Singapore

Central Singapore

Rp3.147.034

Rp3.773.293 total

includes taxes & fees

13 Nov - 14 Nov

A hotel with multiple floors, a swimming pool, and outdoor seating areas.

A modern lounge area with tiered seating, a patterned floor, and a backdrop of greenery.

A modern hotel room with a sofa, armchair, ottoman, and a bed.

A modern restaurant with high ceilings, pendant lighting, and a central bar area.

8. JEN Singapore Tanglin by Shangri-La

Orchard

Rp2.587.107

Rp3.101.942 total

includes taxes & fees

7 Nov - 8 Nov

A high-rise hotel with a prominent Pan Pacific sign, surrounded by other tall buildings and a Ferris wheel in the distance.

A high-rise room with a city view, a table with a drink, and two chairs.

A traditional Japanese-style building with a koi pond and a fountain, surrounded by rocks and greenery.

A spacious room with a large window offering a view of a Ferris wheel and the sea. There is a blue sofa, a table, and a chair with a patterned cushion.

9. Pan Pacific Singapore

Marina Bay

Vithika

Rp5.738.873

Rp6.880.908 total

includes taxes & fees

7 Nov - 8 Nov

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and modern buildings.

A multi-level atrium with a central walkway, balconies with plants, and a water feature.

A modern building with the name 'CONRAD' prominently displayed.

A spacious living area with two sofas, a coffee table, and floor lamps. Large windows provide a view of the cityscape.

10. Conrad Singapore Orchard

Orchard

Dan

Rp4.587.592

Rp5.500.522 total

includes taxes & fees

9 Nov - 10 Nov

A modern dining area with a long wooden table, multiple chairs, and a bar in the background.

A modern bar area with a central island, bar stools, and shelves stocked with bottles and glasses.

A high-rise hotel with multiple floors, a prominent entrance, and a modern architectural design.

11. YOTEL Singapore Orchard Road

Orchard

Dennis

Rp2.335.262

Rp2.799.979 total

includes taxes & fees

1 Nov - 2 Nov

A modern bar area with a view of the city skyline at sunset, featuring wooden flooring, bar stools, and a bar counter.

A modern hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings.

A hotel room with two beds, a desk, a chair, and a large window offering a city view.

A spacious lobby with a large, circular ceiling design and a reception desk.

12. Carlton City Hotel Singapore

Downtown Singapore

Zorana

Rp4.000.149

Rp4.796.178 total

includes taxes & fees

7 Nov - 8 Nov

The exterior of the Voco An IHG Hotel with a distinctive bird sculpture in the entrance.

An outdoor dining area with tables and chairs, a bar with shelves of bottles, and a view of the cityscape at dusk.

A dining area with a long table set for a meal, large windows offering a city view, and modern interior design.

A modern living room with a large window, a sofa, a coffee table, and a chair.

13. voco Orchard Singapore by IHG

Orchard

Mary

Rp3.804.344

Rp4.561.408 total

includes taxes & fees

6 Nov - 7 Nov

A resort with a large swimming pool surrounded by palm trees and a beach.

An outdoor patio area with wooden pergolas, seating arrangements, and a view of a pool and palm trees.

A spacious restaurant with high wooden ceilings and blue-striped seating.

A couple walking on a sandy beach with palm trees and a view of the sea.

14. Shangri-La Rasa Sentosa, Singapore

Sentosa Island

HIROKI

Rp4.895.296

Rp5.869.461 total

includes taxes & fees

14 Nov - 15 Nov

A grand interior with a central spiral staircase, large columns, and a modern reception area.

A balcony with a sofa, a table with a vase of flowers, and a champagne bottle.

A grand hotel lobby with a marble staircase, large columns, and a central atrium.

A rooftop pool with lounge chairs and a table with drinks, overlooking a city skyline and a bridge.

15. The Fullerton Hotel Singapore

Downtown Singapore

Kanaiya

Rp5.175.027

Rp6.204.857 total

includes taxes & fees

13 Nov - 14 Nov

A multi-story hotel with balconies and a pool area in front.

A hotel with a large outdoor pool, multiple balconies, and a well-lit bar area.

A modern bar area with a long wooden table, bar stools, and a well-stocked liquor cabinet.

A modern hotel room with a large sofa set, a dining table, and a city view.

16. Paradox Singapore

Downtown Singapore

Meredith

Rp3.530.162

Rp4.232.664 total

includes taxes & fees

6 Nov - 7 Nov

A rooftop lounge with lounge chairs and a glass balustrade overlooking a cityscape.

A modern hotel room with a city view, a built-in bench, a red armchair, and a small table with a cup and a book.

An outdoor dining area with wicker chairs and a wooden table, surrounded by lush greenery and a small pond.

A modern restaurant with a bar area, red and grey chairs, and a view of greenery through large windows.

17. Quincy Hotel Singapore by Far East Hospitality

Central Singapore

Deeksha

Rp2.793.815

Rp3.349.784 total

includes taxes & fees

7 Nov - 8 Nov

A rooftop infinity pool with green seating and red umbrellas, overlooking a city skyline.

A hotel room with a large bed, a desk with a laptop, a chair, a small table with a drink, and a view of a cityscape through large windows.

A room with a large window overlooking a cityscape at sunset.

A person dining at an outdoor table with a city skyline in the background.

18. JEN Singapore Orchardgateway by Shangri-La

Orchard

Ami

Rp3.635.738

Rp4.359.250 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel with a rooftop pool, lush greenery, and a cityscape view.

A spacious hotel lobby with high ceilings, large windows, and a central bar area.

A high-rise building with a glass exterior and multiple balconies.

A modern hotel with a large glass facade, outdoor seating area with draped canopies, and a well-maintained garden.

19. Pan Pacific Orchard

Orchard

Bridgette

Rp4.895.296

Rp5.869.461 total

includes taxes & fees

6 Nov - 7 Nov

A Holiday Inn Express building with a modern glass facade, a covered entrance, and a landscaped area with trees and shrubs.

A modern cafe with a seating area featuring sofas and round tables, a visible coffee bar, and large windows offering views of the outdoors.

A modern reception desk with a wooden panel wall, a staircase, and red chairs.

A long swimming pool with a cityscape in the background.

20. Holiday Inn Express Singapore Clarke Quay by IHG

Downtown Singapore

Helen

Rp2.642.902

Rp3.286.204 total

includes taxes & fees

7 Nov - 8 Nov

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Stay near popular Dempsey Hill attractions

Lotto Carpets Gallery

You can spend an afternoon studying the exhibits at Lotto Carpets Gallery in Dempsey Hill. Wander through the picturesque gardens and marina in this vibrant area.

See properties

Learn more about Dempsey Hill

This former British military base now houses upscale restaurants and boutiques in lush, colonial-era buildings. Enjoy brunch at PS.Cafe before exploring the art galleries and speciality shops that fill the tranquil hilltop enclave.

See all hotels in Dempsey Hill

A covered outdoor seating area with ceiling fans, tables, and chairs.

Top Dempsey Hill Hotel Reviews

Carlton Hotel Singapore

10/10 Excellent

"Everything"

Hotel Boss

8/10 Good

"nice location for a short stay"

Furama RiverFront

8/10 Good

"Close to a mall good location seemed bizarre on the weekend the restaurant seemed closed off for a wedding yet no reduction in Rate."

YOTEL Singapore Orchard Road

10/10 Excellent

"Great hotel with clean, well-designed rooms and an excellent location. The staff were very helpful and welcoming, and it was a bonus to find vegan options on the restaurant menu. Would happily stay here again!"

Grand Park City Hall

8/10 Good

"Very small gym AC not strong enough But lovely staff"

JEN Singapore Orchardgateway by Shangri-La

10/10 Excellent

"Perfect for price"

lyf Funan Singapore

10/10 Excellent

"Lovely room, clean and quiet. On the smaller side (as expected). Breakfast was decent but also free so no complaints. Excellent location."

Hotel Waterloo Singapore - Handwritten Collection

8/10 Good

"The location is very handy and the staff super friendly. The room was tiny but the mattresses were good and firm and the hotel was fairly quiet. They could provide more tea and coffee in the room though. For two people we only found one tea bag of green tea and one black tea, respectively, and we had to ask for more repetitively."

Marina Bay Sands

10/10 Excellent

"The most extraordinary stay I’ve had. Staff were amazing and their hospitality is top tier. All of the hotel concierge were helpful but when I was facing a huge difficulty with my credit card the front desk agent really put herself in my place and not only understood my problem but solved it. I cannot thank the marina bay sands team for taking care of me during my stay. I am definitely gonna be coming back. Everything was just divine."

More cheap stays in Dempsey Hill

The Quay Hotel Little India

195 Serangoon Rd Singapore

Rp1.243.684

Rp1.491.177 total

2 Nov - 3 Nov

includes taxes & fees

6.8/10 (65 reviews)

Hmlet Essentials Novena

471 Balestier Rd Singapore

Rp1.318.163

Rp1.580.477 total

20 Oct - 21 Oct

includes taxes & fees

8.2/10 Very good! (127 reviews)

BEAT. Arts Hostel Chinatown

211A, South Bridge Road Singapore

Rp1.537.680

Rp1.691.448 total

3 Nov - 4 Nov

includes taxes & fees

6.4/10 (108 reviews)

Beverly Hotels Elements

48 Horne Rd Singapore Singapore

Rp1.699.008

Rp2.037.111 total

15 Oct - 16 Oct

includes taxes & fees

8.4/10 Very good! (136 reviews)

KINN Habitat

5 Hongkong St Singapore

Rp1.764.979

Rp2.116.210 total

8 Nov - 9 Nov

includes taxes & fees

9.2/10 Wonderful! (202 reviews)

Ambassador Transit Hotel Terminal 2

Singapore Changi Airport, PTB2 Singapore

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Frequently asked questions

Where is the best place to stay in Dempsey Hill?

Located 3.5 mi (5.6 km) from the heart of Dempsey Hill, Pan Pacific Singapore is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are JEN Singapore Tanglin by Shangri-La and Carlton Hotel Singapore. See all available top hotels, or vacation rentals in Dempsey Hill.

If I need to cancel my hotel reservation in Dempsey Hill, will I receive a refund?

Yes! The majority of room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Dempsey Hill.

How is it to stay in Dempsey Hill?

Visitors can enjoy all that Dempsey Hill has to offer, including the gardens, shopping and restaurants. Tourists can also enjoy the city's football games and bars. Orchard Road, Universal Studios Singapore and Marina Bay Sands Casino are some of the top sights around the area. There are 793 hotels and other accommodation options in the surrounding area. Find out more about Dempsey Hill.

What is there to see in Dempsey Hill?

A favourite place to visit is Lotto Carpets Gallery. You'll also find Orchard Road and Universal Studios Singapore in the area. Take a look at what more there is to see and do in Expedia's Dempsey Hill guide.

What's the seasonal weather like in Dempsey Hill?

The hottest months are usually May and April, with an average temperature of 28°C, while the coldest months are January and February, with an average of 27°C. The rainiest months in Dempsey Hill are November, December, October and April, with each month seeing an average of 321 mm of rainfall.

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Book Hotels in Dempsey Hill on Expedia.com.sg

Find hotels in Dempsey Hill from Rp1.491.177

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Dempsey Hill

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Dempsey Hill hotels

1. Grand Hyatt Singapore

2. Carlton Hotel Singapore

3. Shangri-La Singapore

4. Four Seasons Hotel Singapore

5. Royal Plaza on Scotts

6. Hilton Singapore Orchard

7. Grand Copthorne Waterfront Hotel Singapore

8. JEN Singapore Tanglin by Shangri-La

9. Pan Pacific Singapore

10. Conrad Singapore Orchard

11. YOTEL Singapore Orchard Road

12. Carlton City Hotel Singapore

13. voco Orchard Singapore by IHG

14. Shangri-La Rasa Sentosa, Singapore

15. The Fullerton Hotel Singapore

16. Paradox Singapore

17. Quincy Hotel Singapore by Far East Hospitality

18. JEN Singapore Orchardgateway by Shangri-La

19. Pan Pacific Orchard

20. Holiday Inn Express Singapore Clarke Quay by IHG

Stay near popular Dempsey Hill attractions

Lotto Carpets Gallery

Learn more about Dempsey Hill

Top Dempsey Hill Hotel Reviews

Carlton Hotel Singapore

Hotel Boss

Furama RiverFront

YOTEL Singapore Orchard Road

Grand Park City Hall

JEN Singapore Orchardgateway by Shangri-La

lyf Funan Singapore

Hotel Waterloo Singapore - Handwritten Collection

Marina Bay Sands

More cheap stays in Dempsey Hill

The Quay Hotel Little India

Hmlet Essentials Novena

BEAT. Arts Hostel Chinatown

Beverly Hotels Elements

KINN Habitat

Ambassador Transit Hotel Terminal 2

Frequently asked questions

Explore a world of travel with Expedia

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