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
Price was S$3,539, price is now S$1,650 per person
S$1,650
per person
17 Jun - 24 Jun
found 18 hours ago
Return flight included
Singapore (SIN) to Tokyo (HND)
9.2/10 Wonderful! (494 reviews)
It was spacious and very close to the train stations.

Reviewed on 22 Apr, 2026

GRAND MONday Ueno OKACHIMACHI

GRAND MONday Ueno OKACHIMACHI

4 out of 5
Taito
Price was S$5,086, price is now S$2,238 per person
S$2,238
per person
24 Jul - 31 Jul
just found
Return direct flight included
Singapore (SIN) to Tokyo (HND)
10/10 Exceptional! (1 review)
I really enjoyed my stay at GRAND MONday Ueno Okachimachi. The best part was definitely the 2nd floor because it had the gym, sauna, vending machine and public bath all right there together. It was so convenient to finish a workout and go straight into the spa to relax. The front desk is staffed and they are super helpful. Having a washer/dryer and a full fridge made everything so much easier. It’s also in a great spot—super close to the station and within walking distance to the markets and Akihabara. I’d definitely stay here again!

Reviewed on 13 May, 2026

GRAND MONday ASAKUSA(Former:MONday Apart Premium Asakusa)

GRAND MONday ASAKUSA(Former:MONday Apart Premium Asakusa)

4 out of 5
Taito
Price was S$4,459, price is now S$1,993 per person
S$1,993
per person
17 Jun - 24 Jun
found 4 hours ago
Return flight included
Singapore (SIN) to Tokyo (HND)
9.8/10 Exceptional! (271 reviews)
Excellent staff, great location and rooms are equipped with everything!

Reviewed on 15 May, 2026

MONday Apart Premium Ueno Okachimachi

MONday Apart Premium Ueno Okachimachi

4 out of 5
Ueno
Price was S$4,144, price is now S$1,866 per person
S$1,866
per person
17 Jun - 24 Jun
found 18 hours ago
Return flight included
Singapore (SIN) to Tokyo (HND)
9.4/10 Exceptional! (614 reviews)
We booked a bed with two twins and a bunk bed because we were traveling as a family of four. Upon arrival we noticed we were missing a set of linens for the bunk beds, and when we brought this to the front desk’s attention they informed us that because our youngest child was 6, they automatically assume they will be co-sleeping with us. We clarified this was NOT the case and they said we could rent a 4th set of linens for 2000 yen/day. Nothing in the Expedia description made note of this, so the charge struck us as very petty. Aside from this misleading marketing, the hotel was quiet, well-located, and clean. Small annoyances like a motion sensor light in the entry (which illuminates the whole room when someone wakes up to use the restroom at night) were solvable with some field ingenuity.

Reviewed on 10 May, 2026

MONday Apart Premium Ueno

MONday Apart Premium Ueno

4 out of 5
Taito
Price was S$3,548, price is now S$1,653 per person
S$1,653
per person
17 Jun - 24 Jun
found 18 hours ago
Return flight included
Singapore (SIN) to Tokyo (HND)
9.4/10 Exceptional! (606 reviews)
The property is clean and convenient but the rooms are quite small. The bunk beds are not comfortable so the room is not suitable for 4 people. The front staff is really nice and cooperative. The facilities are quite basic though for the price

Reviewed on 2 May, 2026

Where to stay in Osaki

Find the best Osaki areas and neighborhoods for the activities you enjoy most. Learn more about Osaki
Shinjuku

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

Hotel Villa Fontaine Grand Haneda Airport - Directly connected to Haneda Airport Terminal 3

Hotel Villa Fontaine Grand Haneda Airport - Directly connected to Haneda Airport Terminal 3

4 out of 5
2-7-1 Hanedakuko, Oota Tokyo Tokyo
Fully refundableReserve now, pay when you stay
The price is S$116 per night from 3 Jun to 4 Jun
S$116
3 Jun - 4 Jun
9.2/10 Wonderful! (11,066 reviews)
Fabricated bathrooms No facial tissues Bathroom was rather small. I guess it was ok for a one night stay. Not sure I would call it GRAND HOTEL it’s conveniently located. Should spend more money on upgrading the rooms rather than the lobby. My two cents

Reviewed on 16 May, 2026

Hotel Villa Fontaine Grand Haneda Airport - Directly connected to Haneda Airport Terminal 3
Hotel Gracery Shinjuku

Hotel Gracery Shinjuku

4 out of 5
1-19-1 Kabukicho, Shinjuku-ku Tokyo Tokyo-to
The price is S$184 per night from 14 Jun to 15 Jun
S$184
14 Jun - 15 Jun
9/10 Wonderful! (5,057 reviews)
I wish the Godzilla terrace was open. The beds are very hard like a board. Great location in the heart of Shinjuku. Good access to subway and train. The limousine bus stop to and from the airport is one block away.

Reviewed on 16 May, 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$113 per night from 7 Jun to 8 Jun
S$113
7 Jun - 8 Jun
8.2/10 Very Good! (3,994 reviews)
Excellent

Reviewed on 16 May, 2026

Shinjuku Washington Hotel Main
See all 6,583 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$1,650. 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.

Popular places to visit

Tokyo Disneyland®

Tokyo Disneyland®

Ride roller coasters and watch theatrical shows as you witness the magic of Disney come to life at this family-friendly amusement park and resort.

Tokyo Disneyland®
東京ディズニーシー

Tokyo DisneySea®

Discover the secrets of the oceans in this magical theme park, where Disney’s sea-dwelling characters will take you on a journey to the world below the waves.

Tokyo DisneySea®
Shibuya Crossing

Shibuya Crossing

Guaranteed to overload the senses, this intersection teeming with people is considered to be a symbol of modern Tokyo.

Shibuya Crossing

Things to do

eSIM: Airalo Japan Package

eSIM: Airalo Japan Package

S$4
per traveller
eSIM: Airalo Japan Package
Boat on the water in Japan with Mount Fuji in the background

Mt Fuji and Hakone 1-Day Tour Return by Bullet Train

S$184
per adult
92% of travellers recommend
Mt Fuji and Hakone 1-Day Tour Return by Bullet Train
Tokyo Tower Observatory Main Deck

Tokyo Tower Observatory Main Deck (150m) Panoramic view Ticket

S$23
per adult
80% of travellers recommend
Tokyo Tower Observatory Main Deck (150m) Panoramic view Ticket
See all activities in Tokyo

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.