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 Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $1,845, price is now CA $1,129 per person
CA $1,129
per person
Jul 17 - Jul 19
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,063 reviews)
This hotel is right in the heart of Times Square—very accessible, clean, and the staff was helpful. Although I wasn’t there much since I was mostly out exploring, I had no issues during my stay. The only minor confusion was that there are two RIU hotels just a couple of blocks from each other, but that’s not a reflection on the hotel itself

Reviewed on Jun 16, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,666, price is now CA $1,531 per person
CA $1,531
per person
Jul 26 - Jul 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,007 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,942, price is now CA $1,137 per person
CA $1,137
per person
Aug 20 - Aug 27
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,144 reviews)
The staff was very nice and they let us check in earlier at no cost. However, the hotel is very old and several things didn’t work like the exhaust fan in the restroom. They had only one small table in the room and that wasn’t enough space to put our stuff on, specifically in the bathroom!

Reviewed on Jun 16, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $4,448, price is now CA $2,774 per person
CA $2,774
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,819, price is now CA $1,159 per person
CA $1,159
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,593 reviews)
Ideal location, everything you need at the hotel with helpful staff. Also, very clean. Look forward to my next stay.

Reviewed on Jun 16, 2026

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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 $156 per night from Jun 29 to Jun 30
CA $156
CA $179 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (2,197 reviews)
"Always feel back home when I see the smiles of the front desk staffs. Great location, convenient to everything! Clean rooms with decent space for travelers like me."

Reviewed on Jun 16, 2026

New Haven Hotel
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 CA $100 per night from Jun 21 to Jun 22
CA $100
CA $116 total
Jun 21 - Jun 22
includes taxes & fees
7.2/10 Good! (1,022 reviews)
"Exactly what I was looking for and an incredibly pleasant stay for a business trip, cheers!"

Reviewed on Jun 15, 2026

Motel 6 New Haven - Branford, CT
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 CA $98 per night from Jun 28 to Jun 29
CA $98
CA $113 total
Jun 28 - Jun 29
includes taxes & fees
6.4/10 (1,023 reviews)
"The first room i had i was literaly stuck to the floor when i went to tell front desk lady was very rude. She did change my room. Im assuming people live there couple arguing hitting the walls salming doors cops. Went to front desk about towels gave 1 wash cloth 2 towels for 2 people"

Reviewed on Jun 9, 2026

Motel 6 Milford, CT
See all 1,095 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

Can I cancel my flight booking to Thimble Islands due to COVID-19?
Many airlines now offer more flexibility due to COVID-19. Our Customer Service Portal will help you answer most questions about flight changes or cancellations. It's also good to check the terms and conditions of your fare — preferably before booking!
What's the best way to find cheap flights to Thimble Islands that have flexible change policies?
At Expedia, we've been channeling our inner yogi to bring you the most flexible airfares in town. Simply tick the "No change fee" box under the filter subheading "Flexible change policies" to find the best flights to Thimble Islands.
What are some of the general tips for travelers to Thimble Islands during the COVID-19 outbreak?
In the face of the COVID-19 outbreak, traveling today comes with more challenges than in the past. Take note of these valuable tips before jumping on your flight to Thimble Islands:
  • Before you book a flight, check if any travel bans or restrictions apply — in both your origin and destination. Stay informed with the latest updates by reviewing government and airport websites.
  • Wear a face mask during airport screening. A TSA officer will ask you to adjust your mask to verify your identity.
  • To reduce the likelihood of cross-contamination, place your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA officer.
  • One container of liquid hand sanitizer is now permitted in your carry-on luggage. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag for X-ray scanning.
  • Empty everything from your pockets, like your keys, phone and wallet, and place them in your carry-on instead of into bins. This will minimize handling during screening.
  • If you're bringing food on the plane with you, place it in a clear plastic bag and then into a scanning bin. This reduces the likelihood that a TSA agent will need to touch your carry-on bag or food container for inspection.

How can I find cheap tickets to Thimble Islands?
One of the best ways to get a hold of cheap tickets to Thimble Islands is to be flexible with your dates. Search for your flights, then click "flexible dates" at the top of your results. It'll bring up the cheapest prices for nearby days. The best price for a flight to Thimble Islands in the last seven days was . Booking in advance will usually help you walk away with an even better deal.
When is the cheapest time to fly to Thimble Islands?
If you can be flexible with what date you travel to Thimble Islands, leave early in the week. The most economical day to take off is generally Tuesday, followed closely by Monday. Saturday is typically the priciest day, with many people preferring to fly on weekends.
How much is a plane ticket to Thimble Islands?
In the last seven days, plane tickets to Thimble Islands varied from to .
Which airlines with flights to Thimble Islands employ COVID-19 cleanliness policies?
From the moment you check in until you leave your arrivals gate, American Airlines has implemented a raft of enhanced measures to help prevent the spread of COVID-19. This carrier operates flights in and out of Thimble Islands and is now providing passenger masks and cleaning with disinfectant.

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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.