Thimble Islands Holidays from AU$2,922

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Thimble Islands Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
per person
28 Oct - 2 Nov
found 14 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8/10 Very Good! (2,135 reviews)
A good hotel to stay at which was convenient for a holiday in New York. Walkable distance to main attractions.

Reviewed on 7 Aug. 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
28 Oct - 2 Nov
found 14 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
7.8/10 Good! (1,511 reviews)
Had a great stay. Would def stay again. Balcony was great!

Reviewed on 10 Aug. 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
28 Oct - 2 Nov
found 14 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (2,085 reviews)
Very happy with my stay at INNSiDE. The staff were all exceptional, the hotel was clean and very trendy. The amenities were lovely, the bed was comfortable and the restaurant was also too notch. We also very much enjoyed the pop up taqueria in the hotel. I would definitely stay there again and I don’t hesitate to recommend it to anyone!

Reviewed on 11 Aug. 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
30 Sept - 6 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.4/10 Very Good! (548 reviews)
Thank you Adrian. She was wonderful and made my mother’s birthday special. Every interaction we had with the staff was positive. The halyard served a delicious lobster roll in a beautiful setting. We will be back.

Reviewed on 9 Aug. 2025

The Knickerbocker Hotel

The Knickerbocker Hotel

5 out of 5
Manhattan
per person
28 Oct - 2 Nov
found 14 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,569 reviews)
Great hotel in very central location

Reviewed on 11 Aug. 2025

Thimble Islands Holiday

Thimble Islands Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)

Our pick of the best Thimble Islands Hotel Deals

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 31 Aug to 1 Sept
AU$238
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (846 reviews)
"Parking was great, although we paid for late check out and was charged an additional fee because we didn’t check out at 11:30. Also, housekeeping did a great job with providing a clean room-but did not know we had late check out and attempted to come into our room at 10:00am. At check out, the front ..."

Reviewed on 10 Aug. 2025

Cambria Hotel New Haven University Area
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 31 Aug to 1 Sept
AU$185
31 Aug - 1 Sept
includes taxes & fees
7.8/10 Good! (1,263 reviews)
"Good place"

Reviewed on 9 Aug. 2025

Best Western Executive Hotel Of New Haven - West Haven
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$267 per night from 27 Aug to 28 Aug
AU$267
27 Aug - 28 Aug
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Good"

Reviewed on 11 Aug. 2025

Omni New Haven Hotel at Yale
See all 992 properties in Thimble Islands
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Thimble Islands holiday package cost?
Tailor make your Thimble Islands package from as low as AU$2,922. 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 holiday 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 holiday 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 holiday 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 holiday?
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 travelling 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 holiday package is the easiest way to organise 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 holiday package?
Yes — that's one of the best things about an Expedia holiday 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 holiday package?
Plans can change unexpectedly, so yes. You may be able to change or cancel your Thimble Islands holiday 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.