Thimble Islands Vacations from ￥373,764

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The Latest Thimble Islands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was ￥534,324, price is now ￥373,764 per person
￥373,764
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to New York (JFK)
8/10 Very Good! (2,471 reviews)
Helpful staff and the rooms are very nice

Reviewed on Jul 10, 2026

5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥1,737,597, price is now ￥1,104,998 per person
￥1,104,998
per person
Sep 19 - Sep 26
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.4/10 Very Good! (5 reviews)

The High Line Hotel

The High Line Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥793,356, price is now ￥546,458 per person
￥546,458
per person
Sep 19 - Sep 26
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (1,006 reviews)
The central air in Room 56 was not working, & someone put in a window air conditioner. The room was 75 degrees because heat was coming in from the side of the window unit. It was over 100degrees on July 4th. Luckily we were able to change rooms and Room 22 was nice & cool. The staff is lovely!

Reviewed on Jul 9, 2026

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was ￥640,978, price is now ￥448,105 per person
￥448,105
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.4/10 Exceptional! (1,490 reviews)
Room was always clean and staff was helpful.

Reviewed on Jul 6, 2026

Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥811,379, price is now ￥574,417 per person
￥574,417
per person
Sep 19 - Sep 26
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
.

Reviewed on Jul 6, 2026

Find the Best Thimble Islands Vacation Packages

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 ￥13,846 per night from Jul 12 to Jul 13
￥13,846
￥15,924 total
Jul 12 - Jul 13
includes taxes & fees
8/10 Very Good! (1,013 reviews)
"The room was hot, and AC barely worked."

Reviewed on Jul 10, 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 ￥19,127 per night from Aug 9 to Aug 10
￥19,127
￥21,997 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (2,217 reviews)
"The hotel feels a bit old and outdated. Service is basic and not particularly attentive."

Reviewed on Jul 10, 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 ￥16,685 per night from Jul 19 to Jul 20
￥16,685
￥19,188 total
Jul 19 - Jul 20
includes taxes & fees
8/10 Very Good! (1,718 reviews)
"Room was clean, parking was easy. The only complaint in which the hotel cannot remedy is the high traffic sounds from the highway."

Reviewed on Jul 10, 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 1,082 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 ￥373,764. 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.