Thimble Islands Holidays from NZ$3,284
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The Latest Thimble Islands Holiday Deals
Price found within the past 48 hours. Click for updated prices.
NobleDEN Hotel
Manhattan
NZ$4,335
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.8/10 Exceptional! (1,643 reviews)
Excellent stay! Great front desk staff. Highly recommend the 7th floor rooms with balconies. Fantastic view!
Reviewed on 19 Sept 2026
Thimble Islands Holiday
Our pick of the best Thimble Islands Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
NZ$270
11 Oct - 12 Oct
includes taxes & fees
9.2/10 Wonderful! (2,328 reviews)
"Enjoyed stay. Would have enjoyed amenities that were not charged separately."
Reviewed on 19 Sept 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
NZ$164
23 Sept - 24 Sept
includes taxes & fees
8/10 Very good! (1,005 reviews)
"Nothing fancy, but clean and nice!"
Reviewed on 19 Sept 2026
Motel 6 Milford, CT
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
NZ$141
27 Sept - 28 Sept
includes taxes & fees
6.6/10 (1,046 reviews)
"B"
Reviewed on 19 Sept 2026
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 holiday package cost?
Tailor make your Thimble Islands package from as low as NZ$3,284. 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
