A densely packed urban landscape with numerous high-rise buildings and a prominent tower in the distance.

Osaki Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

The Latest Osaki Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 19 - Jan 26

    MONday Apart Premium GINZA SHINTOMICHO + Flight

    Chuo
    6 nights
    4.0 star property
    9.4/10 - 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, 2026
    Roundtrip • Vancouver (YVR) - Tokyo (HND)
    YVR - NRT • Nonstop NRT - YVR • Nonstop
    CA $3,802
    CA $1,745
    per traveller
    found 1 day ago
    MONday Apart Premium GINZA SHINTOMICHO
  • Jan 19 - Jan 26

    MONday Apart Premium Ueno Okachimachi + Flight

    Ueno
    6 nights
    4.0 star property
    9.4/10 - Exceptional (762 reviews)
    "We had a fantastic stay at Monday Apart! The rooms were spacious, clean, and very comfortable, making it an excellent choice for our family. The location was convenient, the facilities were great, and everything was well maintained. The staff were friendly and helpful throughout our stay. It was a great home base for exploring Tokyo, and we would happily stay here again. Highly recommended!"
    Reviewed November 11, 2026
    Roundtrip • Vancouver (YVR) - Tokyo (HND)
    YVR - NRT • Nonstop NRT - YVR • Nonstop
    CA $4,667
    CA $1,964
    per traveller
    found 1 day ago
    MONday Apart Premium Ueno Okachimachi
  • Jan 21 - Jan 28

    GRAND MONday Ueno OKACHIMACHI + Flight

    Taito
    6 nights
    4.0 star property
    9.8/10 - Exceptional (125 reviews)
    Roundtrip • Toronto (YYZ) - Tokyo (HND)
    YYZ - HND • 1 stop HND - YYZ • 1 stop
    CA $6,864
    CA $3,172
    per traveller
    found 1 day ago
    GRAND MONday Ueno OKACHIMACHI
  • Jan 25 - Feb 1

    GRAND MONday GINZA + Flight

    Chuo
    6 nights
    4.0 star property
    9.8/10 - Exceptional (366 reviews)
    "Everything was great. Will be back"
    Reviewed November 6, 2026
    Roundtrip • Vancouver (YVR) - Tokyo (HND)
    YVR - HND • 1 stop HND - YVR • 1 stop
    CA $4,956
    CA $2,504
    per traveller
    found 21 hours ago
    GRAND MONday GINZA
  • Jan 21 - Jan 28

    GRAND MONday ASAKUSA(Former:MONday Apart Premium Asakusa) + Flight

    Taito
    6 nights
    4.0 star property
    9.8/10 - Exceptional (351 reviews)
    Roundtrip • Toronto (YYZ) - Tokyo (HND)
    YYZ - HND • 1 stop HND - YYZ • 1 stop
    CA $4,976
    CA $2,523
    per traveller
    found 12 hours ago
    GRAND MONday ASAKUSA(Former:MONday Apart Premium Asakusa)

Where to stay in Osaki

Find the best Osaki areas and neighborhoods for the activities you enjoy most.

Shinjuku

Major commercial hub with the bustling Shinjuku Station, Tokyo Metropolitan Government Building, and various attractions like Kabukichō, Golden Gai, and Shinjuku Gyoen. Shop at flagship stores and enjoy diverse dining options.

Shibuya

Major commercial and finance hub, Shibuya boasts bustling railway stations, trendy fashion scenes in Harajuku and Omotesandō, and vibrant nightlife. Don't miss the iconic Shibuya Crossing and Hachikō statue.

Ginza

Upscale shopping and luxurious dining await in this elegant district, featuring flagship fashion stores, art galleries, and the renowned Sukiyabashi Jiro sushi restaurant. Catch a kabuki performance at Kabuki-za theater or stroll through pedestrian heaven on weekends.

Asakusa

Discover Sensō-ji, a renowned Buddhist temple, and savor traditional Japanese cuisine at local eateries. Explore Kappabashi-dori for kitchenware, cruise the Sumida River, and stay in a cozy ryokan near the Tokyo Metro Ginza Line subway.

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

Osaki Hotel Deals

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 vacation package cost?

Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Osaki from just CA $1,745. And the more you bundle, the more dollars you save. The vacation 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 vacation 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 vacation 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 vacation?

It can be difficult to know when is the ideal time to book your Osaki vacation. 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 vacation is just clicks away.

Can I choose my airline with an Osaki Expedia vacation 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 vacation.

If I'm not able to travel, can I cancel my Osaki vacation package?

Yes you can, and we'll help you every step of the way. You may be able to cancel or change your Osaki vacation 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.