Thimble Islands Vacation Packages

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Top Thimble Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Manhattan
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.2/10 Very Good! (1,310 reviews)
For NYC, this hotel is very average. The rooms are quite small and the bathroom is tiny.

Reviewed on Jul. 24, 2025

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,653 reviews)
Parking like anywhere in New York was hard but $85 per day is a lot. I had to park somewhere else. The room was small and I was hoping for an upgrade but didn’t get it. The bathroom wasn’t that great. I think the hotel was okay. I did get 2 items per day either a drink or snack. I wouldn’t stay with small kids around this area maybe a place that is less chaotic.

Reviewed on Jul. 22, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,714 reviews)
Ideal location for exploring New York. Breakfast buffet was excellent.

Reviewed on Jul. 23, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Very tiny room with no good light, could barely see there. Also blanket doesnt have a cover up. No proper bathroom.

Reviewed on Jul. 17, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (480 reviews)
My only issue was the bed pillows need updating. They weren’t very comfortable, felt old and were faded.

Reviewed on Jul. 22, 2025

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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 CA $176 per night from Aug 11 to Aug 12
CA $176
CA $202 total
Aug 11 - Aug 12
includes taxes & fees
8.8/10 Excellent! (1,671 reviews)
"the bath soap container in shower was empty otherwise great"

Reviewed on Jul. 22, 2025

New Haven Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Aug 24 to Aug 25
CA $184
CA $211 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (817 reviews)
"Awesome stay"

Reviewed on Jul. 19, 2025

Cambria Hotel New Haven University Area
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 CA $131 per night from Aug 3 to Aug 4
CA $131
CA $150 total
Aug 3 - Aug 4
includes taxes & fees
7.8/10 Good! (1,217 reviews)
"After a 6 hours ride we were lucky to get an early check in. The staff was very friendly. Breakfast was always fully stocked and delicious. Would definitely recommend this hotel."

Reviewed on Jul. 19, 2025

Best Western Executive Hotel Of New Haven - West Haven
See all 1,006 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.
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Frequently asked questions

How much does a Thimble Islands vacation package cost?
Tailor make your Thimble Islands package from as low as CA $1,029. 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.