Osaki Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Osaki Holiday Packages
- MONday Apart UENO-SHIN-OKACHIMACHI
15 Jan - 21 JanMONday Apart UENO-SHIN-OKACHIMACHI + Flight
Taito6 nights4.0 star property9.4/10 - Exceptional (529 reviews)"very helpful staff and clean rooms"Reviewed November 13, 2026Return • Singapore (SIN) - Tokyo (HND)SIN - HND • Direct HND - SIN • DirectS$2,544S$1,160found 1 day agoper traveller - MONday Apart Premium GINZA SHINTOMICHO
31 Dec - 6 JanMONday Apart Premium GINZA SHINTOMICHO + Flight
Chuo5 nights4.0 star property9.4/10 - Exceptional (611 reviews)"The room was really spacious and clean. The hotel amenities, services available or lack thereof in lobby was crazy! It is so tiny and nothing extra offered to guests, not even for purchase. No ice machines was crazy as well. Will not stay here again."Reviewed November 9, 2026Return • Singapore (SIN) - Tokyo (HND)SIN - NRT • 1 stop NRT - SIN • 1 stopS$4,009S$1,416found 8 hours agoper traveller - GRAND MONday Ueno OKACHIMACHI
31 Dec - 6 JanGRAND MONday Ueno OKACHIMACHI + Flight
Taito5 nights4.0 star property9.8/10 - Exceptional (126 reviews)Return • Singapore (SIN) - Tokyo (HND)SIN - NRT • 1 stop NRT - SIN • 1 stopS$3,668S$1,520found 8 hours agoper traveller - MONday Apart Premium Akihabara
31 Dec - 6 JanMONday Apart Premium Akihabara + Flight
Akihabara5 nights4.0 star property9.6/10 - Exceptional (443 reviews)"Pretty good stay. Staff knew English and the rooms were clean and spacious. They had water for sale for 50yen at the counter which was very convenient for our Tokyo sight seeing during the day. I would def book this place again the next time I come to Tokyo."Reviewed November 7, 2026Return • Singapore (SIN) - Tokyo (HND)SIN - NRT • 1 stop NRT - SIN • 1 stopS$3,357S$1,465found 8 hours agoper traveller - MONday Apart Hamamatsucho Daimon
31 Dec - 6 JanMONday Apart Hamamatsucho Daimon + Flight
Minato5 nights4.0 star property9.6/10 - Exceptional (466 reviews)"We sent our luggage prior to check in. It was there when we get to the hotel. Check in is very easy, you just scan your passport on the check in counter and it will give you a paper with the codes you needed. They cleaned our room on the 3rd day, changed sheets and tap off amenities, even added extra towels even though we still have a few sets haven’t been used. They provide laundry soap as well. The only down side is check out time is at 10, you have to pay for LCO 25% of the hotel rate and..."Reviewed November 12, 2026Return • Singapore (SIN) - Tokyo (HND)SIN - NRT • 1 stop NRT - SIN • 1 stopS$2,847S$1,278found 8 hours agoper traveller
Where to stay in Osaki
Shinjuku
One of Tokyo's most famous wards has world-class shopping and entertainment options galore.
Shibuya
Step from Tokyo’s busiest train station into streets filled with endless shopping and dining options and the largest concentration of “love hotels” in the city.
Ginza
Named after a silver-coin mint, this district has a long association with affluence. Today it’s where you’ll find some of Japan’s most upmarket labels, restaurants and galleries.
Asakusa
Follow the footsteps of centuries of worshippers along a street filled with traditional snack stalls and through the gates of one of Tokyo’s most popular temples.
Ueno
Try the hanami tradition of admiring flowers as you walk past cherry blossoms and delve into the history of this area through its museums and ornate temples.
Discover the most popular places to visit in Osaki
What to do near Osaki
Mt Fuji and Hakone 1-Day Tour Return by Bullet Train
Tokyo: teamLab Planets TOKYO Digital Art Museum Entry Ticket
Mt.Fuji Hakone Day Tour With Lake Ashi Cruise, FREE Ropeway
Osaki Hotel Deals
"Very convenient location"
"Like the location and accessibility to the station. The room is not spacious, but not as small as the one in Kannai. There is an outlet in the bathroom and the hair dryer is easy to use. The fridge is big and has a freezer. The room has a microwave too. The Kannai one has a massage chair, but this room doesn’t."
"Excelente servicio"
"The ceiling is too low. Im japanese and i hot my head when I had shower!!!!"
"Very close to restaurants and convenient stores."
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$1,160. 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.