Thimble Islands 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 Thimble Islands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 22 - Jan 25

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $1,864
    CA $1,136
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • Jan 25 - Jan 28

    The St. Regis New York + Flight

    Manhattan
    3 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 • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $3,702
    CA $1,939
    per traveller
    found 1 day ago
    The St. Regis New York
  • Feb 4 - Feb 7

    Mandarin Oriental, New York + Flight

    Manhattan
    3 nights
    5.0 star property
    9.2/10 - Wonderful (677 reviews)
    "Excellent stay"
    Reviewed October 26, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $3,333
    CA $2,079
    per traveller
    found 21 hours ago
    Mandarin Oriental, New York
  • Feb 4 - Feb 7

    The Mark + Flight

    Manhattan
    3 nights
    5.0 star property
    9.6/10 - Exceptional (724 reviews)
    "Fire alarm went off three times in middle of the night and no apology or refund."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $4,235
    CA $2,650
    per traveller
    found 21 hours ago
    The Mark
  • Feb 4 - Feb 7

    The Langham, New York, Fifth Avenue + Flight

    Manhattan
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,002 reviews)
    "Very clean, attentive staff and very helpful"
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $2,095
    CA $1,312
    per traveller
    found 21 hours ago
    The Langham, New York, Fifth Avenue

Thimble Islands 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 a Thimble Islands vacation package cost?

Tailor make your Thimble Islands package from as low as CA $1,136. Pick from any combination of flights, hotels and rental cars to craft the escape you've been dreaming about for ages. Be sure to add on a few activities!

How do I get a cheap travel package to Thimble Islands?

Bundle your bookings with Expedia to save big bucks on your next big adventure. With over 550 partner airlines and 1,000,000 hotels worldwide, your Thimble Islands vacation package can be tailored exactly to suit your travel style. With all that extra cash, why not throw in a few interesting activities and tours? It's an easy way to unlock even more bargains. That vacation you've always dreamed of in Thimble Islands is much closer than you thought!

Where should I stay in Thimble Islands?

A getaway to Thimble Islands isn't complete without seeing Stony Creek Museum. Why not book a hotel near this popular tourist attraction?

What are the top hotels in Thimble Islands?

Get your vacation off to a great start by staying at Private Island Victorian Estate. It's one of most sought-after hotels in Thimble Islands. Another leading option is Money Island Home With Deck, Kayak And Paddleboards.

How far in advance should I book my Thimble Islands vacation?

It can be tricky to know when is the ideal time to book your trip to Thimble Islands. But typically the earlier you book, the more affordable the prices. Sometimes, you can lock in your flights and hotels up to 12 months prior to your departure date. If you're eager to escape on a last-minute getaway, no need to stress! There are unbeatable bargains popping up on Expedia every day.

What does an Expedia Thimble Islands travel package include?

It comes down to what you're after. If you're traveling solo, you might decide to bundle flights and hotels. Taking the whole family to Thimble Islands? A travel package including flights, hotels and rental cars might suit you better. Expedia gives you the freedom to tailor your travel package.

What should I know before booking a Thimble Islands travel package?

Bundling your bookings into a Thimble Islands vacation package is the easiest way to organize your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?

Can I choose my airline with a Thimble Islands Expedia vacation package?

Yes — that's one of the best things about an Expedia vacation package. You get to decide. We have more than 550 partner airlines all over the world, so you have loads of choice when creating your Thimble Islands getaway.

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

Plans can change unexpectedly, so yes. You may be able to change or cancel your Thimble Islands vacation package at no cost if you've booked in the last 24 hours. For bookings older than that, you can still make the necessary changes, but your car rental company, hotel or airline may charge additional fees. Looking for more information? Look up our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

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