Thimble Islands Holidays

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    Better together

    Save up to €185 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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    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Thimble Islands

Price found within the past 48 hours. Click for updated prices.
Hotel 27 by LuxUrban
Lotte New York Palace
NobleDEN Hotel
Hotel 32 32
The Mark

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 €133 per night from 25 Aug to 26 Aug
€133
25 Aug - 26 Aug
includes taxes & fees
8.8/10 Excellent! (1,720 reviews)
"The place is nice, but the alley to the opposite street was not pleasant. The hot water from the shower was not constant."

Reviewed on 15 Aug 2025

New Haven Hotel
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 €103 per night from 24 Aug to 25 Aug
€103
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,280 reviews)
I would come again!
"Went for a show in Westville, was decent. Front desk operation was a little slow, but overall a cool area with a convenience store and McDonald’s within walking distance. Very clean room, but the tv and lamp were unplugged and I never bothered to get the tv to work after plugging it in, didn’t stay ..."

Reviewed on 16 Aug 2025

Best Western Executive Hotel Of New Haven - West Haven
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
The price is €73 per night from 21 Aug to 22 Aug
€73
21 Aug - 22 Aug
includes taxes & fees
6.8/10 (1,002 reviews)
"For the low price, this place was fine for one night. There are no amenities (no fridge in the room, no fitness room, no breakfast) but again, you get what you pay for. Otherwise the room was fine and it got the job done."

Reviewed on 4 Aug 2025

Motel 6 New Haven - Branford, CT
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 €888. 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.