Thimble Islands Vacation Packages

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Top Thimble Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,119, price is now CA $694 per person
CA $694
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
Great location!

Reviewed on Jul 13, 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $2,820, price is now CA $1,359 per person
CA $1,359
per person
Sep 13 - Sep 20
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
I love this place. I always choose to go here, but I have been disappointed the last few times that I’ve gone here. I’ve been given rooms where the AC unit is louder than the street. Preventing you from getting a good nights rest then last night I had to go to New York for an emergency and the AC unit in my room was not working and they said they provided a portable little did. I know it was a portable little fan that was blowing hot air I had to take two showers to stay cool and not hyperventilate now wasn’t terribly hot, but I am a person that runs really hot so I need cold AC air and I paid close to $500 on top of that I didn’t even get keys to my room. The maintenance man had to let me in my room. I guess their computer system was on now. The host was nice and kind but very disappointed very disappointed lately.

Reviewed on Jul 13, 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $2,272, price is now CA $1,338 per person
CA $1,338
per person
Aug 22 - Aug 25
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (244 reviews)
The property was absolutely beautiful- so well decorated! The staff was not only helpful and knowledgeable, but also very kind. If you’re looking for a beautiful luxury property, definitely don’t sleep on this one!

Reviewed on Jul 2, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $3,141, price is now CA $1,868 per person
CA $1,868
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
6/10 (2 reviews)
Wrong address no instructions

Reviewed on Jun 18, 2026

Faena New York

Faena New York

5 out of 5
Manhattan
Price was CA $3,518, price is now CA $2,163 per person
CA $2,163
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
9.6/10 Exceptional! (63 reviews)
Amazing service

Reviewed on Jul 5, 2026

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Thimble Islands Hotel Deals

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 CA $124 per night from Jul 22 to Jul 23
CA $124
CA $142 total
Jul 22 - Jul 23
includes taxes & fees
8/10 Very good! (1,016 reviews)
"Still the same wonderful little place as the last time I stayed here!"

Reviewed on Jul 11, 2026

Pier Blue Inn Old Saybrook - Essex
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 $167 per night from Jul 26 to Jul 27
CA $167
CA $193 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (2,221 reviews)
"Great stay and very happy with it."

Reviewed on Jul 13, 2026

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 CA $146 per night from Jul 19 to Jul 20
CA $146
CA $168 total
Jul 19 - Jul 20
includes taxes & fees
8/10 Very good! (1,720 reviews)
"Liked privacy until 30 after ckout time. Disliked they never returned my deposit and charged me 30$ for a late ckout after I asked them if it was okay."

Reviewed on Jul 12, 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 1,086 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 $694. 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.