Thimble Islands Holidays from NZ$906

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The Latest Thimble Islands Holiday Deals

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

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was NZ$1,279, price is now NZ$906 per person
NZ$906
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Boston (BOS) to New York (JFK)
8.8/10 Excellent! (7,641 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was NZ$1,908, price is now NZ$1,233 per person
NZ$1,233
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Boston (BOS) to New York (JFK)
9.2/10 Wonderful! (3,822 reviews)
No complaints. Spent one night there with kids. The hotel was busy and in a great location. It was easy to walk to Times Square and the subway station. The staff were helpful and gracious.

Reviewed on 5 Aug 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was NZ$1,861, price is now NZ$1,206 per person
NZ$1,206
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Boston (BOS) to New York (JFK)
9/10 Wonderful! (3,255 reviews)
The only issue with the room...of the bathroom light was on, you could see the person in the shower...the full silhouette at least. Breakfast was great as it was included with our rate. The cost was a tad higher than I wanted to pay at over $500 for 1 night, but the experience and location were wonderful.

Reviewed on 5 Aug 2026

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
Price was NZ$1,687, price is now NZ$1,105 per person
NZ$1,105
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Boston (BOS) to New York (JFK)
9.4/10 Exceptional! (1,498 reviews)
Staff was absolutely amazing. So warm, friendly, and helpful. Room was very nice, clean, comfortable. Wouldn’t hesitate to stay there again.

Reviewed on 2 Aug 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was NZ$1,293, price is now NZ$936 per person
NZ$936
per person
20 Oct - 22 Oct
found 1 day ago
Return flight included
Boston (BOS) to New York (JFK)
6.8/10 (2,037 reviews)
The room was horrible !! The bed was so thin and the blinds were terrible all beat up with holes. The noise from the street was so loud. The bathroom was literally like showering on the street!!! I would never stay there and we left during the night!!! Horrible stay! Do not waste any money here! They cheated some few per day that I’m trying to dispute. !!! We didn’t charge anything we didn’t even stay for 24 hours

Reviewed on 4 Aug 2026

Thimble Islands Holiday

Our pick of the best Thimble Islands Hotel Deals

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Fully refundable
The price is NZ$125 per night from 3 Sept to 4 Sept
NZ$125
3 Sept - 4 Sept
includes taxes & fees
7.2/10 Good! (1,011 reviews)
"Staff was nice but definitely the worst hotel I ever stayed at not even close, smelled bad, bed was the worst, but for $150 for two nights I knew what I was getting into lol"

Reviewed on 4 Aug 2026

Motel 6 New Haven - Branford, CT
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is NZ$213 per night from 6 Aug to 7 Aug
NZ$213
6 Aug - 7 Aug
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Room was clean enough, but in dire need of updating. Poor lighting, heavy on wood details, the bathtub had a large crack right in the middle. Carpet felt like it needed a good professional cleaning. We weren't aware of any "amenities" the property offered, but we only stayed 1 night. Staff was ..."

Reviewed on 4 Aug 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 NZ$270 per night from 31 Aug to 1 Sept
NZ$270
31 Aug - 1 Sept
includes taxes & fees
New Haven Hotel
See all 1,096 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 holiday package cost?
Tailor make your Thimble Islands package from as low as NZ$906. 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 holiday 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 holiday 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 holiday 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 holiday?
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 travelling 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 holiday package is the easiest way to organise 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 holiday package?
Yes — that's one of the best things about an Expedia holiday 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 holiday package?
Plans can change unexpectedly, so yes. You may be able to change or cancel your Thimble Islands holiday 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.