Thimble Islands Vacations

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Find the Best Thimble Islands Vacation Packages

Thimble Islands Hotel Deals

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 NT$3,772 per night from Jul 26 to Jul 27
NT$3,772
NT$4,338 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (2,193 reviews)
"If you're looking for a downtown hotel for a night or two, this is a great location. Parking is available in the ramp across the street. Easy peasy. Lobby is large, rooms are clean. My only suggestion is the front desk staff needs to be a bit more informed about the area.... what's open later at ..."

Reviewed on 2026/7/2

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 NT$2,072 per night from Jul 19 to Jul 20
NT$2,072
NT$2,383 total
Jul 19 - Jul 20
includes taxes & fees
6.6/10 (1,011 reviews)
"The water pressure is good in the shower."

Reviewed on 2026/7/2

Motel 6 Milford, CT
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
291 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is NT$4,236 per night from Jul 12 to Jul 13
NT$4,236
NT$4,871 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Design, staff, roomy and clean"

Reviewed on 2026/7/2

Hilton Garden Inn Milford
See all 1,092 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 vacation 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 vacation 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 vacation 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 vacation 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 vacation?
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 traveling 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 vacation package is the easiest way to organize 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 vacation package?
Yes — that's one of the best things about an Expedia vacation 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 vacation package?
Plans can change unexpectedly, so yes. You may be able to change or cancel your Thimble Islands vacation 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.