Thimble Islands Vacation Packages

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Top Thimble Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $1,594, price is now CA $963 per person
CA $963
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (4,436 reviews)
It was a little confused about the big bus promotions

Reviewed on May 27, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $5,745, price is now CA $2,879 per person
CA $2,879
per person
Jul 12 - Jul 15
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

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,186, price is now CA $1,892 per person
CA $1,892
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,005 reviews)
Loved the location and the great views

Reviewed on May 25, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $2,781, price is now CA $1,699 per person
CA $1,699
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (151 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower. But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker. Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door. It’s little odd things that just made it not feel like a luxury stay. And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use. The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.

Reviewed on Mar 24, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $3,427, price is now CA $2,244 per person
CA $2,244
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,011 reviews)
Nice property great location

Reviewed on May 21, 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 $190 per night from Jun 7 to Jun 8
CA $190
CA $218 total
Jun 7 - Jun 8
includes taxes & fees
9.2/10 Wonderful! (2,142 reviews)
"Front desk staff made my check in quick and easy, answered my questions re: parking w/o issue. Since we arrived after 8pm, I really appreciated the security of the parking garage across the street (gated w/ key card access) and the ease of getting to the hotel from the sky bridge. The room was clean ..."

Reviewed on May 27, 2026

New Haven Hotel
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jun 21 to Jun 22
CA $175
CA $202 total
Jun 21 - Jun 22
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"The bathroom was too small. The coffee maker didn’t work well."

Reviewed on May 27, 2026

Omni New Haven Hotel at Yale
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is CA $346 per night from Jun 11 to Jun 12
CA $346
CA $422 total
Jun 11 - Jun 12
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"The location and the amenities provided by the hotel was first classed"

Reviewed on May 27, 2026

Water's Edge Resort & Spa
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.
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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.