Thimble Islands Packages (Flight + Hotel)

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    Save up to ฿27,000 when you book a flight and hotel together*

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Top hotels in Thimble Islands

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is ฿4,109 per night from 25 Nov to 26 Nov
฿4,109
฿4,725 total
25 Nov - 26 Nov
includes taxes & fees
9.2/10 Wonderful! (2,400 reviews)
"I was very impressed with the front desk staff and housekeeping staff. Unfortunately, my room had a smell I couldn’t quite identify…the next morning my bathroom had about a dozen ants surrounding the trash can and surrounding floor. Then it hit me…the smell was chemical like pest treatment chemicals. ..."

Reviewed on 31 Oct 2026

New Haven Hotel
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
The price is ฿2,364 per night from 19 Nov to 20 Nov
฿2,364
฿2,719 total
19 Nov - 20 Nov
includes taxes & fees
6.6/10 (1,062 reviews)
"Idk"

Reviewed on 30 Oct 2026

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

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is ฿2,577 per night from 1 Nov to 2 Nov
฿2,577
฿2,963 total
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (1,005 reviews)
"I'm not sure how this hotel has good ratings. It is run down and in disrepair. My door would not even open per the front desk clerk so she walked me to my room where the door was open slightly and said here's your key but you can't really use it because the door is so stiff it won't open from the ..."

Reviewed on 30 Oct 2026

Pier Blue Inn Old Saybrook - Essex
See all 1,082 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 . 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.