Thimble Islands Vacation Packages

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Top Thimble Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was CA $3,110, price is now CA $1,845 per person
CA $1,845
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Staff were very accomodating and looked after my family well during our stay. Nothing was too difficult for them.

Reviewed on Jan 17, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $3,267, price is now CA $2,010 per person
CA $2,010
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby.

Reviewed on Feb 2, 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $3,505, price is now CA $2,194 per person
CA $2,194
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (159 reviews)
Staff were lovely, helpful and pleasant. Turndown service way too late, though—9:45 might catch some guests sleeping.

Reviewed on Jan 3, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,579, price is now CA $3,003 per person
CA $3,003
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
The entire stay was exceptional! From the point of entry to departure 10/10

Reviewed on Jan 29, 2026

The Pierre, A Taj Hotel, New York

The Pierre, A Taj Hotel, New York

5 out of 5
Manhattan
Price was CA $2,804, price is now CA $1,883 per person
CA $1,883
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (1,007 reviews)
Staff warm, & welcoming, bar, great breakfast, & restaurant lovely, don’t miss coffee at the bar in the morning & Friday with the Martinis piano singers.

Reviewed on Feb 5, 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 refundable
The price is CA $156 per night from Feb 15 to Feb 16
CA $156
CA $179 total
Feb 15 - Feb 16
includes taxes & fees
9/10 Wonderful! (2,016 reviews)
Excellent desk staff. Clean and quite room. Good location.

Reviewed on Feb 4, 2026

New Haven Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Fully refundable
The price is CA $141 per night from Mar 8 to Mar 9
CA $141
CA $162 total
Mar 8 - Mar 9
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Nice fromt desk staff. Clean & comfortable room.

Reviewed on Jan 26, 2026

Cambria Hotel New Haven University Area
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 $81 per night from Feb 18 to Feb 19
CA $81
CA $94 total
Feb 18 - Feb 19
includes taxes & fees
6.2/10 (1,003 reviews)
My room was immaculate and the staff were very kind and easy to work with check-in was a breeze. It’s a good location near to stores and restaurants. It was very affordable. The shower pressure was great. Everything was great. The beds were comfortable. Sheets white and fresh. As a student, this ...

Reviewed on Jan 31, 2026

Motel 6 Milford, CT
See all 1,046 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.