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.
MONday Apart Premium GINZA SHINTOMICHO

MONday Apart Premium GINZA SHINTOMICHO

4 out of 5
Chuo
Save 100% on your flight
Price was S$2,269, price is now S$1,140 per person
S$1,140
per person
13 Mar - 18 Mar
found 1 day ago
Return direct flight included
Singapore (SIN) to Tokyo (TYO)
9.2/10 Wonderful! (422 reviews)
When we booked our flights our seats were together and when it was time for departure our seats were all considered unassigned. I was able to chat with a representative that put our seats together which was what we needed especially since both of our daughters were struggling to sit with strangers and had multiple accidents on our flight to Japan.

Reviewed on 29 Dec, 2025

Hotel Chinzanso Tokyo

Hotel Chinzanso Tokyo

5 out of 5
Bunkyo
Price was S$3,641, price is now S$1,810 per person
S$1,810
per person
23 Mar - 27 Mar
found 1 day ago
Return flight included
Singapore (SIN) to Tokyo (TYO)
9.8/10 Exceptional! (1,053 reviews)
Great hotel, amazing garden, awesome dining options and service. Spacious rooms, comfortable King size bed. Second stay here, will be back next time we're in Tokyo.

Reviewed on 31 Dec, 2025

MONday Apart Asakusabashi Akihabara(Former：MONday Apart Akihabara Southeast)

MONday Apart Asakusabashi Akihabara(Former：MONday Apart Akihabara Southeast)

4 out of 5
Taito
Save 100% on your flight
Price was S$2,772, price is now S$1,464 per person
S$1,464
per person
22 Mar - 28 Mar
found 16 hours ago
Return flight included
Singapore (SIN) to Tokyo (TYO)
9.6/10 Exceptional! (327 reviews)
Great value hotel close to Akihabara in a quiet part of it. Laundry in the room is a plus! No breakfast but plenty of options for that around. Light that turns on automatically and does not turn off after more than 30 mins is quite annoying.

Reviewed on 10 Dec, 2025

Premium hotel MONday MAIHAMA View I

Premium hotel MONday MAIHAMA View I

3.5 out of 5
Edogawa
Save 100% on your flight
Price was S$2,051, price is now S$1,156 per person
S$1,156
per person
13 Mar - 18 Mar
found 1 day ago
Return direct flight included
Singapore (SIN) to Tokyo (TYO)
No reviews
MONday Apart Premium NIHONBASHI

MONday Apart Premium NIHONBASHI

4 out of 5
Chuo
Save 100% on your flight
Price was S$2,259, price is now S$1,282 per person
S$1,282
per person
13 Mar - 18 Mar
found 1 day ago
Return direct flight included
Singapore (SIN) to Tokyo (TYO)
9.6/10 Exceptional! (726 reviews)
We had a wonderful stay. The amenities, location and staff are wonderful. Will definitely stay here again for future trips.

Reviewed on 19 Dec, 2025

Where to stay in Osaki

Find the best Osaki areas and neighborhoods for the activities you enjoy most. Learn more about Osaki
Shinjuku showing a city, night scenes and street scenes

Shinjuku

4.5/5(477 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

Hotel Villa Fontaine Grand Haneda Airport

4 out of 5
2-7-1 Hanedakuko, Oota Tokyo Tokyo
Fully refundableReserve now, pay when you stay
The price is S$111 per night from 6 Jan to 7 Jan
S$111
6 Jan - 7 Jan, 2026
9.2/10 Wonderful! (8,928 reviews)
Really convenient location at Terminal 3, 1st floor, sign for the pathway to hotel is right outside of the international arrival gate. The room is clean, staff are friendly. The breakfast was decent. The room is a bit on the smaller side compared to some of the hotels. The heat was a bit much, so ...

Reviewed on 29 Dec, 2025

Hotel Villa Fontaine Grand Haneda Airport
Shinjuku Washington Hotel Main

Shinjuku Washington Hotel Main

4 out of 5
3-2-9 Nishishinjuku Tokyo Tokyo-to
The price is S$132 per night from 2 Jan to 3 Jan
S$132
2 Jan - 3 Jan, 2026
8/10 Very Good! (3,639 reviews)
Great Hotel! Many Stores and Restaurants inside as well.

Reviewed on 29 Dec, 2025

Shinjuku Washington Hotel Main
Tokyo Bay Shiomi Prince Hotel

Tokyo Bay Shiomi Prince Hotel

4 out of 5
2-8-16 Shiomi Tokyo Tokyo
Fully refundableReserve now, pay when you stay
The price is S$263 per night from 26 Jan to 27 Jan
S$263
26 Jan - 27 Jan, 2026
9.6/10 Exceptional! (4,305 reviews)
Great hotel for families traveling with young kids. Tokyo Bay Shiomi Prince Hotel is comfortable, clean, and very convenient. Super easy access to central Tokyo and a quick ride to Disneyland. The breakfast spread is excellent with plenty of options. Highly recommend staying here!

Reviewed on 29 Dec, 2025

Tokyo Bay Shiomi Prince Hotel
See all 6,204 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$1,140. 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®

4.5/5(122 reviews)

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®
Tokyo DisneySea®

Tokyo DisneySea®

4.5/5(38 reviews)

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

4.5/5(269 reviews)

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$189
per adult
92% of travellers recommend
Mt Fuji and Hakone 1-Day Tour Return by Bullet Train
eSIM: Airalo Japan Package

eSIM: Airalo Japan Package

S$5
per traveller
eSIM: Airalo Japan Package
Tokyo Skytree standing tall against a stunning sunset backdrop, with Mount Fuji in the distance.

Tokyo Skytree Admission Ticket with Tembo Deck and Galleria

S$19
per adult
80% of travellers recommend
Tokyo Skytree Admission Ticket with Tembo Deck and Galleria
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.