Thimble Islands Trips (flight + hotel)

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to P 3,118 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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 P7,163 per night from Jul 13 to Jul 14
P7,163
P8,237 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (1,610 reviews)
"The women at the front desk were fabulous! Everyone was very helpful, solicitous and just plain nice."

Reviewed on Jun 29, 2025

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 P4,728 per night from Jul 2 to Jul 3
P4,728
P5,437 total
Jul 2 - Jul 3
includes taxes & fees
6/10 (1,003 reviews)
"Staff super friendly, respectful and helpful! However rooms requires refurbished"

Reviewed on Jun 27, 2025

Motel 6 Milford, CT
Red Roof Inn Milford - New Haven
Red Roof Inn Milford - New Haven
2 out of 5
10 Rowe Ave, Milford, CT
Fully refundableReserve now, pay when you stay
The price is P5,203 per night from Jul 1 to Jul 2
P5,203
P5,984 total
Jul 1 - Jul 2
includes taxes & fees
7/10 Good! (1,005 reviews)
"This is an old not updated hotel. There are alot of new amenities that could be added, but for 100$ a night its hard to complain. There was not a refrigerator or coffee maker in the room. The AC was medicore and a large gap between the door and wall. They do not have USB ports in the room, however ..."

Reviewed on Jun 21, 2025

Red Roof Inn Milford - New Haven
See all 1,010 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.