Thimble Islands All inclusive Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 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

Top All inclusive vacation packages in Thimble Islands

Price found within the past 48 hours. Click for updated prices.
  • Jan 14 - Jan 20

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    6 nights
    4.0 star property
    9.0/10 - Wonderful (3,463 reviews)
    "This was a mixed bag for me. Some of the staff -- like the person who started my check-in process, and the bellhop -- were very kind and friendly. But one staff member felt nearly antagonistic. I also experienced intentional misgendering of my friend staying with me, which ruined it for me. It's a lot of money to spend to see your friend mistreated. The guests' "guessed" genders are listed on the informational receipt -- nowhere did I add them. If you are LGBTQ+, I recommend skipping this hotel...."
    Reviewed November 14, 2026
    Roundtrip • Tokyo (HND) - New York (JFK)
    HND - LGA • 1 stop LGA - HND • 1 stop
    ¥337,932
    ¥253,960
    per traveler
    found 1 day ago
    Hotel Riu Plaza New York Times Square
  • Jan 14 - Jan 20

    The St. Regis New York + Flight

    Manhattan
    6 nights
    5.0 star property
    9.2/10 - Wonderful (295 reviews)
    "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"
    Reviewed November 6, 2026
    Roundtrip • Tokyo (HND) - New York (JFK)
    HND - LGA • 1 stop LGA - HND • 1 stop
    Save 100% on your flight
    ¥961,075
    ¥599,008
    per traveler
    found 1 day ago
    The St. Regis New York
  • Jan 14 - Jan 20

    JW Marriott Essex House New York + Flight

    Manhattan
    6 nights
    4.5 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • Tokyo (HND) - New York (JFK)
    HND - LGA • 1 stop LGA - HND • 1 stop
    ¥463,683
    ¥323,747
    per traveler
    found 1 day ago
    JW Marriott Essex House New York
  • Jan 14 - Jan 20

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    6 nights
    4.0 star property
    9.2/10 - Wonderful (4,164 reviews)
    "The bar cafe in the lobby was amazing! Quick check in, clean property and very spacious rooms for this price point in NYC"
    Reviewed November 13, 2026
    Roundtrip • Tokyo (HND) - New York (JFK)
    HND - EWR • 1 stop LGA - HND • 1 stop
    ¥368,353
    ¥269,937
    per traveler
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • Jan 29 - Feb 4

    The William Hotel Midtown, New York + Flight

    Manhattan
    6 nights
    3.5 star property
    9.4/10 - Exceptional (305 reviews)
    Roundtrip • Tokyo (TYO) - New York (JFK)
    HND - LGA • 1 stop EWR - HND • 1 stop
    ¥352,596
    ¥266,385
    per traveler
    found 4 hours ago
    The William Hotel Midtown, New York

All-inclusive Thimble Islands vacations: everything you need to know

Can I book a Thimble Islands vacation with airfare and meals?

On an all-inclusive vacation, your mind and body can wander far from your wallet. Pay one simple price when you bundle your accommodation and airfare, and you avoid all those yucky bills after conversation-starting cocktails or decadent dinners.

How can I find Thimble Islands all-inclusive vacations that are adults only?

All the best all-inclusive, all-adult vacations are a click of a filter or two away. Choose from great grown-up features. Say, a spa for a couple’s massage, a hot tub to soak away the stresses of the day, or a swim-up bar to get the party started.

How much is an all-inclusive trip to Thimble Islands?

Affordable all-inclusive is yours, whatever your budget. Packages start tempting you from just ¥253,960. Prices and availability are subject to change. Additional terms may apply.

How can I book cheap all-inclusive trips to Thimble Islands?

Whenever you book your travel, sorting by price and filtering by budget shows you what’s out there in your price range.

What are the benefits of all-inclusive Thimble Islands vacations with airfare?

Create your dream getaway by bundling your flight and hotel and you get delightful deals and discounts. Add your car rental, too, and you save on all three.

What should I think about when I book an all-inclusive Thimble Islands family vacation package?

With little tummies taken care of, you just need to put smiles on their faces. Easy! Book an all-inclusive vacation with a full-on water park or epic pools—or book your stay near the world’s biggest theme parks and attractions.

Why should I book an all-inclusive honeymoon package in Thimble Islands?

You can start your married life how you mean to go on with an all-inclusive honeymoon package. Eat and drink to your heart’s content, waltz around in happy harmony, and have your fill of delights. Together, you can book up adventure excursions and return to a pool-side cabana for cocktails at sunset.

Can I book an all-inclusive Thimble Islands package with free cancellation and/or flexible dates?

When you’re searching for your all-inclusive getaway, filter your results by payment option to find free cancellation and buy now, pay later options. That way, you can rebook without worry, should your plans change.

Why should I book an all-inclusive Thimble Islands package vacation with Expedia?

Book amazing all-inclusive adventures, all in one place. Choose from a vast inventory of deals, adding every little extra to build your brilliant break in minutes.