Osaki Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Osaki

Price found within the past 48 hours. Click for updated prices.
MONday Apart Premium Ueno

MONday Apart Premium Ueno

4 out of 5
Taito
Price was CA $3,600, price is now CA $2,204 per person
CA $2,204
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Tokyo (HND)
9.4/10 Exceptional! (619 reviews)
good！nice and clean, will come again

Reviewed on Jun 11, 2026

GRAND MONday ASAKUSA(Former:MONday Apart Premium Asakusa)

GRAND MONday ASAKUSA(Former:MONday Apart Premium Asakusa)

4 out of 5
Taito
Price was CA $4,836, price is now CA $2,701 per person
CA $2,701
per person
Sep 5 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Tokyo (HND)
9.8/10 Exceptional! (275 reviews)
Loved the sauna and the large tub

Reviewed on May 29, 2026

GRAND MONday GINZA

GRAND MONday GINZA

4 out of 5
Chuo
Price was CA $5,647, price is now CA $3,311 per person
CA $3,311
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Tokyo (HND)
9.8/10 Exceptional! (256 reviews)
Very clean and stylish hotel. Accommodations like complimentary umbrellas, washer & dryer, laundry detergent, and bottled waters helped our stay in a foreign country. The staff were very professional and kind. Taking care of our luggage on checkout day also helped us enjoy one more day of travel.

Reviewed on Jun 12, 2026

Premium MONday ASAKUSA I

Premium MONday ASAKUSA I

3.5 out of 5
Taito
Price was CA $4,294, price is now CA $2,575 per person
CA $2,575
per person
Sep 5 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Tokyo (HND)
No reviews
MONday Apart Premium NIHONBASHI

MONday Apart Premium NIHONBASHI

4 out of 5
Chuo
Price was CA $4,380, price is now CA $2,853 per person
CA $2,853
per person
Jul 25 - Jul 31
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tokyo (HND)
9.6/10 Exceptional! (810 reviews)
I honestly wish I could have stayed at this property longer. The staff, room and amenities were great. I would love to stay there again.

Reviewed on Jun 13, 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(551 area reviews)

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.

Find hotels in Shinjuku

Osaki Hotel Deals

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 CA $142 per night from Jun 28 to Jun 29
CA $142
CA $161 total
Jun 28 - Jun 29
9.2/10 Wonderful! (11,557 reviews)
"The staff were very friendly and helpful. The room is very clean and smells so good. It’s a plus that it’s inside the airport. We love it so much!!!"

Reviewed on Jun 13, 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 CA $146 per night from Jun 29 to Jun 30
CA $146
CA $177 total
Jun 29 - Jun 30
9/10 Wonderful! (5,142 reviews)
"Room was fine, hotel feel was very cold to travellers. Very different from our stays in other hotels."

Reviewed on Jun 13, 2026

Hotel Gracery Shinjuku
Shinjuku Granbell Hotel

Shinjuku Granbell Hotel

4 out of 5
2-14-5 Kabuki-cho Tokyo Tokyo-to
The price is CA $109 per night from Jul 6 to Jul 7
CA $109
CA $120 total
Jul 6 - Jul 7
8.6/10 Excellent! (2,206 reviews)
"Staff was incredible and the breakfast buffet was very good and diverse. Good location, but it is a little far from shinjuku station if you are walking. We took the train from the airport and walked with our luggage from shinjuku station. Worth getting a cab from that station, because its nearly ..."

Reviewed on Jun 11, 2026

Shinjuku Granbell Hotel
See all 6,658 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $2,204. 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.

Stay near popular Osaki attractions

Irugi Shrine

Irugi Shrine is just one of the places to see in Tokyo, so why not enjoy the other things to explore during your travels? Make time to visit the area's shops, or simply enjoy its top-notch restaurants.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.