Dempsey Hill Holiday Rentals, Singapore: Private House Rentals

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Our top choices for Dempsey Hill hotels

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

A modern lobby with a central seating area, a staircase, and a wall with greenery.

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

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

1. JEN Singapore Tanglin by Shangri-La

Orchard

Darren

฿5,198

฿6,232 total

includes taxes & fees

13 Sept - 14 Sept

A spacious lobby with a central clock, seating areas, and a polished floor.

The Orchard Hotel building with a modern glass facade and signage.

A buffet with various food items and drinks.

A hallway with a polished marble floor, wooden paneling, and decorative screens.

2. Orchard Hotel Singapore

Orchard

shailee

฿5,198

฿6,232 total

includes taxes & fees

11 Sept - 12 Sept

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 modern conference room with a long table, chairs, and a projector.

3. YOTEL Singapore Orchard Road

Orchard

Dennis

฿3,533

฿4,236 total

includes taxes & fees

11 Sept - 12 Sept

A modern hotel corridor with a glass railing, a staircase, and a view of the building's interior.

A hotel reception area with a modern design, featuring a reception desk, a red sofa, and a large window offering a view of the cityscape.

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

A long swimming pool with a cityscape in the background.

4. Holiday Inn Express Singapore Clarke Quay by IHG

Downtown Singapore

Jason

฿4,756

฿5,921 total

includes taxes & fees

18 Sept - 19 Sept

A hotel with a prominent 'Orchard Rendezvous Hotel' sign, large windows, and a modern architectural design.

A swimming pool with tiled flooring, lounge chairs, and a bar area.

A hotel room with a large bed, a desk with a laptop, a chair, a small table with a plant, and a large window with a view.

A bar area with high stools, a bar counter, and shelves with bottles and glasses.

5. Orchard Rendezvous Hotel by Far East Hospitality

Orchard

Kavitha

฿3,976

฿4,768 total

includes taxes & fees

13 Sept - 14 Sept

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

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

An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge areas.

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

6. Shangri-La Singapore

Tanglin

Chien Liang

฿9,139

฿10,958 total

includes taxes & fees

22 Sept - 23 Sept

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 long buffet table with various cheeses, fruits, and flowers.

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

7. Conrad Singapore Orchard

Orchard

Youngeun

฿8,311

฿9,965 total

includes taxes & fees

13 Sept - 14 Sept

A Novotel hotel with a modern design, featuring a rooftop pool with illuminated tiles.

A modern hotel with a glass facade, named Mercure and Novotel, featuring a central courtyard with green landscaping.

A modern hotel room with a large bed, a seating area, and a glass partition.

A modern interior with a geometric patterned wall, a marble reception desk, and shelves with decorative items and monitors.

8. Novotel Singapore on Stevens

Tanglin

Matti

฿4,366

฿5,235 total

includes taxes & fees

13 Sept - 14 Sept

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.

9. Royal Plaza on Scotts

Orchard

Tushar

฿5,276

฿6,326 total

includes taxes & fees

10 Sept - 11 Sept

A hotel room with a large bed, a wooden headboard, and a mural of a garden with unique structures.

A modern interior with a seating area, a coffee machine, and a shelf with decorative items.

A rooftop pool with lounge chairs, a lifebuoy, and a city skyline in the background.

A hallway with a patterned wall, a marble floor, and a ceiling with recessed lighting.

10. Days Inn by Wyndham Singapore Novena

Novena

Dennis Justin

฿2,496

฿2,992 total

includes taxes & fees

22 Sept - 23 Sept

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

A modern hotel room with a city view, a sofa set, yellow chairs, and a large window.

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

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.

11. JEN Singapore Orchardgateway by Shangri-La

Orchard

Gabbrielle

฿6,753

฿8,097 total

includes taxes & fees

13 Sept - 14 Sept

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

A hotel room with two beds, a sitting area, and a view of a cityscape at night.

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

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

12. Grand Copthorne Waterfront Hotel Singapore

Singapore River

฿5,848

฿7,011 total

includes taxes & fees

12 Sept - 13 Sept

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

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

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

An indoor restaurant with wicker furniture, hanging plants, and a stone wall.

13. Four Seasons Hotel Singapore

Orchard

David

฿11,893

฿14,259 total

includes taxes & fees

26 Sept - 27 Sept

A buffet setup with various food containers and utensils.

A modern reception desk with a wooden finish, a glass display case with various bottles, and a digital kiosk.

A gym with treadmills, weight machines, and free weights.

A modern hotel with a glass facade, a visible entrance, and a sign for 'Holiday Inn Express'.

14. Holiday Inn Express Singapore Orchard Road by IHG

Orchard

Doris

฿5,536

฿6,949 total

includes taxes & fees

19 Sept - 20 Sept

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.

A modern hotel with a prominent 'quintet' sign, featuring a grid of balconies, large windows, and a mix of glass and brown facade.

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

15. Quincy Hotel Singapore by Far East Hospitality

Newton

฿5,191

฿6,224 total

includes taxes & fees

10 Sept - 11 Sept

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 outdoor pool area with lounge chairs and umbrellas, surrounded by a vertical garden and a contemporary building facade.

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

16. Hilton Singapore Orchard

Orchard

Benjamin

฿8,522

฿10,218 total

includes taxes & fees

25 Sept - 26 Sept

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 rooftop pool with lounge chairs and umbrellas, surrounded by high-rise buildings.

17. Carlton Hotel Singapore

Downtown Core

ROY

฿5,457

฿6,542 total

includes taxes & fees

12 Sept - 13 Sept

A swimming pool surrounded by palm trees and lounge chairs.

A hotel room with two beds, a desk, a chair, a TV, and a balcony with a view of buildings and greenery.

An outdoor pool area with tables and chairs, surrounded by greenery and buildings in the background.

A bar area with a long counter, stools, and shelves of bottles.

18. Goodwood Park Hotel

Orchard

Jacqueline

฿7,951

฿9,533 total

includes taxes & fees

16 Sept - 17 Sept

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

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.

A rooftop pool with lounge chairs and a cityscape view.

19. voco Orchard Singapore by IHG

Orchard

Nicola Hazel

฿7,225

฿8,663 total

includes taxes & fees

25 Sept - 26 Sept

A multi-level atrium with a central open space surrounded by seating areas and staircases.

A modern hotel entrance with a glass facade, a fountain, and a landscaped area with steps leading up to the entrance.

A bar area with stools, a counter, and shelves of bottles.

A spacious lobby with a modern design, featuring a central seating area with sofas and a staircase leading to upper levels.

20. Holiday Inn Singapore Atrium by IHG

Bukit Merah

HARRY

฿4,938

฿5,921 total

includes taxes & fees

11 Sept - 12 Sept

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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

Crowne Plaza Changi Airport by IHG

10/10 Excellent

"Great hotel. Very handy for a nightly stopover on the way through to Europe. Wonderful room’s restaurant & bar."

Pan Pacific Singapore

10/10 Excellent

"Extremely clean, helpful staff. Near by shops and great places to eat. Close by to all the main attractions. Pool small however very nice and relaxing"

Paradox Singapore

10/10 Excellent

"Excellent location, amenities, food and service. Nice, spacious rooms."

YOTEL Singapore Orchard Road

10/10 Excellent

"Great stay, good location. Perfect for any holiday style."

Mercure ICON Singapore City Centre

10/10 Excellent

"Great hotel, but gym is small and essentially a few treadmills."

V Hotel Lavender

10/10 Excellent

"Very friendly staff and everything was near by. The room was neat and clean although it was small compare of other hotel rooms but it does the job."

Hotel Boss

8/10 Good

"Good location, friendly staff"

Mandai Rainforest Resort By Banyan Tree

10/10 Excellent

"Mandai resort was beautiful, immersed in nature, with luxurious, spacious rooms, and great amenities overall. The breakfast spread was one of the most expansive I've seen, featuring both Western and Eastern dishes. From the moment you are greeted to the complimentary drink service when you are waiting in the lobby to check out, the staff and service are of the highest standard. All of this combined with the accessibility to Mandai's Zoo experiences make this a beautiful and relaxing resort a must-stay in Singapore."

Carlton Hotel Singapore

10/10 Excellent

"Once again an enjoyable stay at a hotel that has a great location."

More cheap stays in Dempsey Hill

The Quay Hotel Little India

195 Serangoon Rd Singapore

฿1,902

฿2,281 total

21 Sept - 22 Sept

includes taxes & fees

7.2/10 Good! (57 reviews)

BEAT. Arts Hostel Chinatown

211A, South Bridge Road Singapore

฿2,679

฿2,947 total

18 Sept - 19 Sept

includes taxes & fees

Days Inn by Wyndham Singapore Novena

592 Balestier Road Singapore

฿2,496

฿2,992 total

22 Sept - 23 Sept

includes taxes & fees

Beverly Hotels Elements

48 Horne Rd Singapore Singapore

฿2,830

฿3,393 total

10 Sept - 11 Sept

includes taxes & fees

KINN Habitat

5 Hongkong St Singapore

฿3,058

฿3,667 total

15 Sept - 16 Sept

includes taxes & fees

Ambassador Transit Hotel Terminal 2

Singapore Changi Airport, PTB2 Singapore

฿4,877

฿5,848 total

9 Sept - 10 Sept

includes taxes & fees

8.2/10 Very good! (1,007 reviews)

Frequently asked questions

Where is the best place to stay in Dempsey Hill?

Located 3.4 mi (5.5 km) from the heart of Dempsey Hill, Hotel Boss is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Pan Pacific Singapore and JEN Singapore Tanglin by Shangri-La. 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 798 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 ฿2,281

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Dempsey Hill

Check prices for these dates

Filter by

Star rating

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Our top choices for Dempsey Hill hotels

1. JEN Singapore Tanglin by Shangri-La

2. Orchard Hotel Singapore

3. YOTEL Singapore Orchard Road

4. Holiday Inn Express Singapore Clarke Quay by IHG

5. Orchard Rendezvous Hotel by Far East Hospitality

6. Shangri-La Singapore

7. Conrad Singapore Orchard

8. Novotel Singapore on Stevens

9. Royal Plaza on Scotts

10. Days Inn by Wyndham Singapore Novena

11. JEN Singapore Orchardgateway by Shangri-La

12. Grand Copthorne Waterfront Hotel Singapore

13. Four Seasons Hotel Singapore

14. Holiday Inn Express Singapore Orchard Road by IHG

15. Quincy Hotel Singapore by Far East Hospitality

16. Hilton Singapore Orchard

17. Carlton Hotel Singapore

18. Goodwood Park Hotel

19. voco Orchard Singapore by IHG

20. Holiday Inn Singapore Atrium by IHG

Stay near popular Dempsey Hill attractions

Lotto Carpets Gallery

Learn more about Dempsey Hill

Top Dempsey Hill Hotel Reviews

Crowne Plaza Changi Airport by IHG

Pan Pacific Singapore

Paradox Singapore

YOTEL Singapore Orchard Road

Mercure ICON Singapore City Centre

V Hotel Lavender

Hotel Boss

Mandai Rainforest Resort By Banyan Tree

Carlton Hotel Singapore

More cheap stays in Dempsey Hill

The Quay Hotel Little India

BEAT. Arts Hostel Chinatown

Days Inn by Wyndham Singapore Novena

Beverly Hotels Elements

KINN Habitat

Ambassador Transit Hotel Terminal 2

Frequently asked questions

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