Thimble Islands Trip

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Top Thimble Islands Flight + Hotel Deals

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

Radio Hotel

4 out of 5
Manhattan
Price was ₹84,946, price is now ₹60,799 per person
₹60,799
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
Staff was great but that’s about it. Rooms and bathrooms are extremely small. You can hear everything from the hallways

Reviewed on 1 Jul 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was ₹104,891, price is now ₹69,756 per person
₹69,756
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
Great location!! Staff was helpful !! Only downside was no ventilation. Rest all is good !

Reviewed on 8 Jul 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ₹137,921, price is now ₹93,325 per person
₹93,325
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,652 reviews)
I would definitely stay here again.

Reviewed on 8 Jul 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 ₹135,291, price is now ₹91,636 per person
₹91,636
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,130 reviews)
If you pay for breakfast make sure you go down around 730-8am. Tried calling there’s front desk and they never answered. The staff was really nice thought, the bellman and the cleaning staff. There’s a lot of security which is nice makes you feel safer.

Reviewed on 7 Jul 2026

CIVILIAN Hotel

CIVILIAN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was ₹91,779, price is now ₹63,508 per person
₹63,508
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (1,962 reviews)
I cannot say enough good things about this place. The staff was incredibly helpful with parking and navigating the area, and the room was amazing. I loved the view, the blinds, the beds, and the bathroom. The rooftop bar was fantastic, and the location truly can’t be beat, just a few blocks from Times Square and Hell’s Kitchen. This will absolutely be my go-to spot whenever I’m in Manhattan.

Reviewed on 7 Jul 2026

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 ₹11,286 per night from 26 Jul to 27 Jul
₹11,286
₹12,979 total
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (2,209 reviews)
"Nice hotel, good location, helpful staff"

Reviewed on 7 Jul 2026

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 ₹6,172 per night from 22 Jul to 23 Jul
₹6,172
₹7,098 total
22 Jul - 23 Jul
includes taxes & fees
6.6/10 (1,016 reviews)
"I enjoy my stay there very good but hard to get to places around the area for eating and dining."

Reviewed on 6 Jul 2026

Motel 6 Milford, CT
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
291 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is ₹11,708 per night from 2 Aug to 3 Aug
₹11,708
₹13,464 total
2 Aug - 3 Aug
includes taxes & fees
8.6/10 Excellent! (1,025 reviews)
"The place is excellent.. Second Stay there in a month!"

Reviewed on 6 Jul 2026

Hilton Garden Inn Milford
See all 1,090 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 ₹60,799. 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.