Osaki Holidays

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    Save up to S$134 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
GRAND MONday Ueno OKACHIMACHI

GRAND MONday Ueno OKACHIMACHI

2 out of 5
Taito
Price was S$2,706, price is now S$1,281 per person
S$1,281
per person
8 Jun - 13 Jun
found 11 hours ago
Return flight included
Singapore (SIN) to Tokyo (HND)
No reviews
GRAND MONday GINZA

GRAND MONday GINZA

4 out of 5
Chuo
Price was S$4,347, price is now S$1,865 per person
S$1,865
per person
14 May - 20 May
found 12 hours ago
Return direct flight included
Singapore (SIN) to Tokyo (HND)
9.8/10 Exceptional! (207 reviews)
Everything was perfect! The location, the room, the staff. Tai was amazing at helping us with restaurants to luggage transfers. We can’t wait to come back!

Reviewed on 31 Mar, 2026

Premium Apart MONday GINZA EAST

Premium Apart MONday GINZA EAST

4 out of 5
Chuo
Price was S$3,841, price is now S$1,686 per person
S$1,686
per person
14 May - 20 May
found 12 hours ago
Return direct flight included
Singapore (SIN) to Tokyo (HND)
9.6/10 Exceptional! (150 reviews)
The laundry service was great. The kitchen and staff were great. Some mild smell of cigarette smoke but otherwise no other concerns.

Reviewed on 30 Mar, 2026

Premium Apart MONday HAMAMATSUCHO Station

Premium Apart MONday HAMAMATSUCHO Station

4 out of 5
Minato
Price was S$3,951, price is now S$1,745 per person
S$1,745
per person
14 May - 20 May
found 12 hours ago
Return direct flight included
Singapore (SIN) to Tokyo (HND)
No reviews
MONday Apart Premium Ueno Okachimachi

MONday Apart Premium Ueno Okachimachi

4 out of 5
Ueno
Price was S$3,482, price is now S$1,558 per person
S$1,558
per person
14 May - 20 May
found 12 hours ago
Return direct flight included
Singapore (SIN) to Tokyo (HND)
9.4/10 Exceptional! (567 reviews)
The rooms are a bit smaller than they look in the pictures, but still good size. Five of us (three adults, two kids) in there was a bit cramped with all our luggage, but we still managed. Having a kitchenette was very convenient. The train is close by, but not too noisy and stopped running from midnight to 6am, so not too disruptive. Overall, well worth it.

Reviewed on 30 Mar, 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$117 per night from 27 Apr to 28 Apr
S$117
27 Apr - 28 Apr
9.2/10 Wonderful! (10,425 reviews)
This hotel is the perfect landing place if your priority is to be right by the airport and you need a quiet respite after touring the town. The onsen makes the stay so worthwhile. The food options were challenging but the customer service made up for it. Every train ride into Tokyo will take 45 minutes ...

Reviewed on 31 Mar, 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$218 per night from 28 Apr to 29 Apr
S$218
28 Apr - 29 Apr
9/10 Wonderful! (4,854 reviews)
The location is perfect!

Reviewed on 31 Mar, 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$134 per night from 29 Apr to 30 Apr
S$134
29 Apr - 30 Apr
8.2/10 Very Good! (3,819 reviews)
Toilet is not that great, location is fantastic

Reviewed on 31 Mar, 2026

Shinjuku Washington Hotel Main
See all 6,403 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$1,281. 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®
Attractions disneysea mediterranean harbor mountain and dock in tokyo,japan; Shutterstock ID 529713217

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®
Tokyo Skytree

Tokyo Skytree

Find yourself wowed by stunning 360-degree panoramic views of Tokyo from its newest and highest tower.

Tokyo Skytree

Things to do

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 admission ticket

Japan Tokyo Tower Observatory Deck E-Ticket

S$23
per adult
84% of travellers recommend
Japan Tokyo Tower Observatory Deck E-Ticket
Full-Day Sightseeing Bus Tour in Tokyo with Cruise

Full-Day Sightseeing Bus Tour in Tokyo with Cruise

S$157
per adult
92% of travellers recommend
Full-Day Sightseeing Bus Tour in Tokyo with Cruise
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.