Osaki Vacations from $1,167

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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

Your Osaki Vacation

Book your vacation package to Osaki and prepare to experience its shopping and beyond. Whether you're craving adventure or relaxation, it's waiting for you in this inviting neighborhood. Want to sightsee during your trip to Osaki? Make sure you stop by nearby attractions such as Tokyo Tower, Nezu Art Museum and Mori Art Museum. Expedia will help you turn your ideal Osaki vacation into reality, no matter your travel plans or budget.

The Latest Osaki Vacation Packages

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

MONday Apart Premium Ueno

4 out of 5
Taito
Save 100% on your flight
Price was $2,349, price is now $1,167 per person
$1,167
per person
Feb 9 - Feb 15
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Tokyo (TYO)
18.8/10 Exceptional! (464 reviews)
Very happy with the stay here. Room was comfortable and quiet. Lots of konbinis, restaurants and small supermarkets close by. Note that the nearest train station is about a ten minute walk but it’s flat so not so difficult and didn’t bother us. Would consider staying at Monday Apart again!

Reviewed on Nov 18, 2025

GRAND MONday GINZA

GRAND MONday GINZA

4 out of 5
Chuo
Price was $3,411, price is now $1,543 per person
$1,543
per person
Feb 9 - Feb 15
found 24 hours ago
Roundtrip flight included
Los Angeles (QLA) to Tokyo (TYO)
19.6/10 Exceptional! (154 reviews)
A family of 4 with 2 young kids. Super convenient and very friendly staff. Didn't hear neighbours at all even with a baby next door.

Reviewed on Nov 20, 2025

MONday Apart Premium Asakusa

MONday Apart Premium Asakusa

4 out of 5
Taito
Price was $3,118, price is now $1,454 per person
$1,454
per person
Feb 9 - Feb 15
found 21 hours ago
Roundtrip flight included
Los Angeles (QLA) to Tokyo (TYO)
19.6/10 Exceptional! (210 reviews)
The room was spacious and clean with great amenities. Staff was friendly and helpful. The location is excellent. Quiet neighborhood but minutes away from the train station. So many shops, eateries and beautiful Sensoji Temple within walking distance. I would definitely stay here again.

Reviewed on Nov 12, 2025

MONday Apart Premium Ueno Okachimachi

MONday Apart Premium Ueno Okachimachi

4 out of 5
Ueno
Price was $2,974, price is now $1,391 per person
$1,391
per person
Feb 9 - Feb 15
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Tokyo (TYO)
18.8/10 Exceptional! (516 reviews)
Clean room. Friendly staff. Nice hotel thanks.

Reviewed on Nov 19, 2025

MONday Apart Premium GINZA SHINTOMICHO

MONday Apart Premium GINZA SHINTOMICHO

4 out of 5
Chuo
Save 100% on your flight
Price was $2,408, price is now $1,189 per person
$1,189
per person
Feb 9 - Feb 15
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Tokyo (TYO)
18.4/10 Exceptional! (422 reviews)
We loved our stay here! We have a 7 and a 5 year old so staying in a quieter part of town that was still very accessible to the subway was wonderful.

Reviewed on Nov 16, 2025

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

Where to stay in Osaki

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

Shinjuku

4.5/5(2,072 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

Hotel Villa Fontaine Grand Haneda Airport

4 out of 5
2-7-1 Hanedakuko, Oota Tokyo Tokyo
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $127 total per night from Dec 1 to Dec 2
$127 total
Dec 1 - Dec 2
9.2/10 Wonderful! (8,247 reviews)
Easy option walking to terminal 3 Haneda

Reviewed on Nov 16, 2025

Hotel Villa Fontaine Grand Haneda Airport
Hotel Gracery Shinjuku

Hotel Gracery Shinjuku

4 out of 5
1-19-1 Kabukicho, Shinjuku-ku Tokyo Tokyo-to
$181 nightly
The price is $199 total per night from Dec 17 to Dec 18
$199 total
Dec 17 - Dec 18
8.8/10 Excellent! (4,248 reviews)
Professional staff, clean rooms, but loud during the day

Reviewed on Nov 17, 2025

Hotel Gracery Shinjuku
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
$258 nightly
The price is $284 total per night from Dec 18 to Dec 19
$284 total
Dec 18 - Dec 19
9.6/10 Exceptional! (4,093 reviews)
All of the above

Reviewed on Nov 19, 2025

Tokyo Bay Shiomi Prince Hotel
See all 6,144 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Osaki

Tokyo Disneyland® featuring rides and night scenes

Tokyo Disneyland®

4.5/5(612 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(254 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 Dome

Tokyo Dome

4.5/5(382 reviews)

Catch an event at Tokyo Dome during your trip to Tokyo. Amble within picturesque gardens or visit the temples in this vibrant area.

Tokyo Dome

Things to do

Official Street Go-Kart in Shibuya

Official Street Go-Kart in Shibuya

$101
per adult
Official Street Go-Kart in Shibuya
Shibuya Official Street Go-Kart in Shibuya Annex

Shibuya Official Street Go-Kart in Shibuya Annex

$82
per adult
Shibuya Official Street Go-Kart in Shibuya Annex
See all activities in Tokyo
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.