Osaki Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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
Price found within the past 48 hours. Click for updated prices.
MONday Apart Premium GINZA SHINTOMICHO

MONday Apart Premium GINZA SHINTOMICHO

4 out of 5
Chuo
Save 100% on your flight
Price was S$2,074, price is now S$1,039 per person
S$1,039
per person
31 Jul - 4 Aug
found 1 day ago
Return flight included
Singapore (SIN) to Tokyo (HND)
9.4/10 Exceptional! (515 reviews)
We love that we had enough space for 5 people. It was very near to 2 train stations. We were early for check in but they took us anyway.

Reviewed on 16 Jun, 2026

MONday Apart Premium Ueno

MONday Apart Premium Ueno

4 out of 5
Taito
Save 100% on your flight
Price was S$2,410, price is now S$1,131 per person
S$1,131
per person
31 Jul - 4 Aug
found 1 day ago
Return flight included
Singapore (SIN) to Tokyo (HND)
9.4/10 Exceptional! (640 reviews)
I am not sure what was the smell but my room smelled like sweat and armpit we were hardly in the room but once we got there the stench would come back the hotel offered to move us but we had so much stuff that we decided to just deal with it

Reviewed on 28 Jun, 2026

Nohga Hotel Ueno Tokyo

Nohga Hotel Ueno Tokyo

4 out of 5
Taito
Save 100% on your flight
Price was S$2,127, price is now S$1,126 per person
S$1,126
per person
7 Aug - 12 Aug
found 6 hours ago
Return direct flight included
Singapore (SIN) to Tokyo (HND)
9.6/10 Exceptional! (1,010 reviews)
服務人員態度都很好，房間乾淨整潔空間寬敞，整體來說是一間非常舒服的飯店

Reviewed on 30 Jun, 2026

Premium MONday ASAKUSA I

Premium MONday ASAKUSA I

4 out of 5
Taito
Save 100% on your flight
Price was S$2,491, price is now S$1,339 per person
S$1,339
per person
31 Jul - 4 Aug
found 1 day ago
Return flight included
Singapore (SIN) to Tokyo (HND)
9.4/10 Exceptional! (9 reviews)
Crazy good value. Place is brand new. Everything is incredibly clean. Shower is amazing. The room was massive. Great AC. All the appliances are new. Will absolutely stay here again. Not removing a star for this, but the keypad entry thing for the elevator is annoying - it's like the one thing they cheaped out on during the remodel and it makes no sense given the quality of everything else.

Reviewed on 30 Jun, 2026

Hotel Chinzanso Tokyo

Hotel Chinzanso Tokyo

5 out of 5
Bunkyo
Price was S$3,201, price is now S$1,742 per person
S$1,742
per person
7 Aug - 12 Aug
found 6 hours ago
Return direct flight included
Singapore (SIN) to Tokyo (HND)
9.8/10 Exceptional! (1,115 reviews)
The staff were friendly, the rooms were clean and big, the food was great. The view of the garden was fantastic! The sea of clouds and fireflies were magical!

Reviewed on 23 Jun, 2026

Where to stay in Osaki

Find the best Osaki areas and neighborhoods for the activities you enjoy most. Learn more about Osaki
A busy urban street at night with illuminated billboards and a prominent Epson sign.

Shinjuku

4.5/5(480 area reviews)

One of Tokyo's most famous wards has world-class shopping and entertainment options galore.

Find hotels in Shinjuku

Top hotels in Osaki

Shinjuku Granbell Hotel

Shinjuku Granbell Hotel

4 out of 5
2-14-5 Kabuki-cho Tokyo Tokyo-to
The price is S$107 per night from 6 Jul to 7 Jul
S$107
6 Jul - 7 Jul
8.6/10 Excellent! (2,243 reviews)
"."

Reviewed on 29 Jun, 2026

Shinjuku Granbell Hotel
Hotel Gracery Shinjuku

Hotel Gracery Shinjuku

4 out of 5
1-19-1 Kabukicho, Shinjuku-ku Tokyo Tokyo-to
The price is S$197 per night from 20 Jul to 21 Jul
S$197
20 Jul - 21 Jul
9/10 Wonderful! (5,176 reviews)
"The hotel was very nice and clean and fun. The rooms were fine. My biggest issue was it took me three hours to dry a load of laundry one night and that was frustrating."

Reviewed on 30 Jun, 2026

Hotel Gracery Shinjuku
Shinjuku Washington Hotel Main

Shinjuku Washington Hotel Main

4 out of 5
3-2-9 Nishishinjuku Tokyo Tokyo-to
The price is S$106 per night from 6 Jul to 7 Jul
S$106
6 Jul - 7 Jul
8.2/10 Very good! (4,121 reviews)
"I don’t like"

Reviewed on 30 Jun, 2026

Shinjuku Washington Hotel Main
See all 6,689 properties in Osaki
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.

Frequently asked questions

How much does an Osaki holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Osaki from just S$1,039. And the more you bundle, the more dollars you save. The holiday of your dreams has never been more affordable.
How do I get a cheap travel package to Osaki?
Bundle your hotel and flight bookings, add extras such as activities, and save with an Osaki holiday package. You won't just walk away with big discounts on your getaway — you'll have a world of choice too. When you book through Expedia, you'll have your pick of over 550 air carriers and 1,000,000 hotels around the world. Your next big adventure begins right here, right now!
Where should I stay in Osaki?
Most people who travel to Osaki include both Tokyo Tower and Tokyo Skytree on their must-see lists. Why not select a hotel near these top attractions?
What are the top hotels in Osaki?
Get your holiday off to a good start by reserving a room at Hotel MyStays Gotanda Station. It's one of most sought-after properties in Osaki. Another comfortable option is Hotel Royal Oak Gotanda.
How far in advance should I book my Osaki holiday?
It can be difficult to know when is the ideal time to book your Osaki holiday. But typically the earlier you book, the better the prices. In some cases, you can reserve your flights and hotels nearly a year before your departure date. If you're eager to escape on a last-minute getaway, no need to panic! There are fantastic deals announced on Expedia every day.
What does an Expedia Osaki travel package include?
With Expedia, you can select a combination of flights, car rentals and hotels to build your ideal Osaki package. Once you've made your booking, you can add on the fun stuff like day tours and activities. Don't forget, the more you bundle, the greater the savings!
What should I know before booking an Osaki travel package?
Tailor deals that match your budget with an Expedia package. Hotels, flights, rental cars — we have them all. You'll save a packet just for bundling your bookings. Whether you're embarking on a ski adventure or sipping cocktails on a beach, your ideal holiday is just clicks away.
Can I choose my airline with an Osaki Expedia holiday package?
Expedia offers access to more than 550 partner airlines worldwide, so you definitely can. Just select your preferred carrier and craft your ideal Osaki holiday.
If I'm not able to travel, can I cancel my Osaki holiday package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or change your Osaki holiday package at no cost within 24 hours of booking. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, have a look at our Customer Service Portal for more information.

Stay near popular Osaki attractions

O Art Museum

You can spend an afternoon studying the exhibits at O Art Museum in Tokyo. Discover the fascinating museums and notable monuments in this vibrant area.
See properties

Explore a world of travel with Expedia

* 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.