Thimble Islands Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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

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Thimble Islands Flight & Hotel Packages

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

Night Hotel Broadway

Manhattan
S$2,291
per person
20 Oct - 26 Oct
found 3 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
7.6/10 Good! (3,584 reviews)
The rooms were outdated bathroom floor was disgusting the door of the bathroom look like it was falling apart the elevators was disgusting very small

Reviewed on 15 Sept, 2026

The William Hotel Midtown, New York

The William Hotel Midtown, New York

Manhattan
Save 100% on your flight
S$3,080
per person
20 Oct - 26 Oct
found 3 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.4/10 Exceptional! (232 reviews)
Ink 48 Hotel

Ink 48 Hotel

Manhattan
S$2,655
per person
20 Oct - 26 Oct
found 3 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.4/10 Very good! (1,767 reviews)
If neighborhood isn’t an issue then this is an affordable option with decent rooms. Don’t expect luxury.

Reviewed on 16 Sept, 2026

Freehand New York

Freehand New York

Manhattan
S$2,657
per person
20 Oct - 26 Oct
found 3 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.6/10 Excellent! (2,135 reviews)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

Manhattan
S$3,078
per person
19 Oct - 25 Oct
found 1 hour ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.2/10 Wonderful! (2,337 reviews)
Great location and room was more spacious than most in the city.

Reviewed on 15 Sept, 2026

Top hotels in Thimble Islands

New Haven Hotel

New Haven Hotel

229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
S$196
29 Sept - 30 Sept
includes taxes & fees
New Haven Hotel
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
S$119
22 Sept - 23 Sept
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Room need complete makeover"

Reviewed on 15 Sept, 2026

Pier Blue Inn Old Saybrook - Essex
Motel 6 Milford, CT

Motel 6 Milford, CT

111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
S$102
24 Sept - 25 Sept
includes taxes & fees
Motel 6 Milford, CT
See all 1,084 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.

Frequently asked questions

How much does a Thimble Islands holiday package cost?
Tailor make your Thimble Islands package from as low as S$2,291. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.