Osaki Vacations from $2,169

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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 Okachimachi

MONday Apart Premium Ueno Okachimachi

4 out of 5
Ueno
Price was $3,345, price is now $2,169 per person
$2,169
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Tokyo (HND)
9.4/10 Exceptional! (604 reviews)
Everything's clean and convenient to everything, either food, shopping, or transportation. It would be great if they will offer or have an option for room cleaning depends on what the guests wants without additional payment. Currently, the cleaning is only after couple of days, I think it was 3 days after check in.

Reviewed on May 1, 2026

GRAND MONday GINZA

GRAND MONday GINZA

4 out of 5
Chuo
Save 100% on your flight
Price was $4,290, price is now $2,583 per person
$2,583
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Tokyo (HND)
9.8/10 Exceptional! (239 reviews)
Increíble para viajar con familia, me encantó

Reviewed on Apr 29, 2026

GRAND MONday ASAKUSA(Former:MONday Apart Premium Asakusa)

GRAND MONday ASAKUSA(Former:MONday Apart Premium Asakusa)

4 out of 5
Taito
Save 100% on your flight
Price was $3,950, price is now $2,399 per person
$2,399
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Tokyo (HND)
9.8/10 Exceptional! (267 reviews)
Great location, lots to do around, the hotel itself is on a fairly quite residential street couple of blocks removed from the busy streets of Asakusa. My family of 4 stayed there for 6 nights. Very clean and nicely furnished studio style apartment/ suite.

Reviewed on Apr 30, 2026

GRAND MONday Ueno OKACHIMACHI

GRAND MONday Ueno OKACHIMACHI

4 out of 5
Taito
Price was $3,955, price is now $2,500 per person
$2,500
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Tokyo (HND)
No reviews
TABI UENO

TABI UENO

4 out of 5
Taito
Price was $4,114, price is now $2,744 per person
$2,744
per person
Jun 12 - Jun 17
found 22 hours ago
Roundtrip flight included
Los Angeles (LAX) to Tokyo (HND)
10/10 Exceptional! (9 reviews)
Great hotel! the rooms were so clean, the staff were very friendly. The location was conveniently close to UENO train station and the train that takes you directly to Narita Airport. Would 100% return to this hotel if I’m ever back in Tokyo.

Reviewed on May 2, 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(2,090 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
$86 nightly
The price is $97 total per night from Jun 3 to Jun 4
$97 total
Jun 3 - Jun 4
9.2/10 Wonderful! (10,968 reviews)
Staff are incredibly accommodating and helpful. I needed to book an additional night for myself as my partner’s flight is a day earlier than mine, and the staff at the front desk were incredible with assisting me through that process. The rooms itself were spacious and the amenities within the room ...

Reviewed on May 7, 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
$128 nightly
The price is $141 total per night from May 8 to May 9
$141 total
May 8 - May 9
9/10 Wonderful! (4,998 reviews)
Clean room Ac. And quiet

Reviewed on May 7, 2026

Hotel Gracery Shinjuku
Shinjuku Washington Hotel Main

Shinjuku Washington Hotel Main

4 out of 5
3-2-9 Nishishinjuku Tokyo Tokyo-to
$75 nightly
The price is $82 total per night from May 8 to May 9
$82 total
May 8 - May 9
8.2/10 Very Good! (3,985 reviews)
Location was great. However the room was terrible! Cramped, no storage space, noisy, and the negatives could go on. The outside of the building looked like a high-rise jail block house. And the room seemed like a prison cell. We had a single double bed that was pushed up to one wall and only allowed ...

Reviewed on May 6, 2026

Shinjuku Washington Hotel Main
See all 6,544 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®

Tokyo Disneyland®

4.5/5(619 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®
Attractions disneysea mediterranean harbor mountain and dock in tokyo,japan; Shutterstock ID 529713217

Tokyo DisneySea®

4.5/5(257 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®
東京ドーム

Tokyo Dome

4.5/5(387 reviews)

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

Tokyo Dome

Things to do

Tokyo Go Kart: Asakusa, Skytree, and Akihabara **IDP MUST**

Tokyo Go Kart: Asakusa, Skytree, and Akihabara **IDP MUST**

$94
per adult
94% of travellers recommend
Tokyo Go Kart: Asakusa, Skytree, and Akihabara **IDP MUST**
Tokyo After 5: Small Group Evening Food Tasting Tour

Tokyo Evening Food Adventure: Hidden Eateries & Local Flavours

$61
per adult
90% of travellers recommend
Tokyo Evening Food Adventure: Hidden Eateries & Local Flavours
Vegan-Friendly Tokyo Sumo Show, Mochi-Pounding Dinner Experience

Vegan-Friendly Tokyo Sumo Show, Mochi-Pounding Dinner Experience

$101
per adult
Vegan-Friendly Tokyo Sumo Show, Mochi-Pounding Dinner Experience
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.