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 AKA NoMad

Hotel AKA NoMad

4 out of 5
Manhattan
Price was CA $2,018, price is now CA $1,245 per person
CA $1,245
per person
May 18 - May 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,003 reviews)
The staff at the front desk, led by AJ, are excellent

Reviewed on Mar 15, 2026

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Price was CA $2,834, price is now CA $1,589 per person
CA $1,589
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,957 reviews)
Avoid this place during the Christmas season if you want personal assistance

Reviewed on Mar 13, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $4,297, price is now CA $2,487 per person
CA $2,487
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,005 reviews)
The staff was very friendly and the ambience was nice. However, the room was very cramped and had to be careful not to fall over columns and bed on the way to the bathroom. Walls were thin and there was no facial soap provided.

Reviewed on Mar 13, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was CA $3,051, price is now CA $1,840 per person
CA $1,840
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,002 reviews)
Hotel is very nice great location and rooms were very nice and clean. Staff was very friendly.

Reviewed on Mar 16, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was CA $2,532, price is now CA $1,577 per person
CA $1,577
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (1,547 reviews)
Great friendly staff, they are very helpful. The hotel was great, clean and the rooms were awesome. Balcony was a nice area, and the roof top view was great. Would stay agian.

Reviewed on Mar 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
The price is CA $113 per night from Mar 30 to Mar 31
CA $113
CA $131 total
Mar 30 - Mar 31
includes taxes & fees
9/10 Wonderful! (2,032 reviews)
Great

Reviewed on Mar 16, 2026

New Haven Hotel
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Apr 5 to Apr 6
CA $139
CA $160 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (1,280 reviews)
I didn't think the property was so old, however its furniture & fixtures certainly were. Upon arrival to my room, noticed a LONG, thin hair on the edge of the bathroom tub. There wasn't ONE employee that spoke to and/or welcomed me first. Once engaged, they were nice. Being given a "list" of what ...

Reviewed on Mar 16, 2026

Hyatt Place Milford / New Haven
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
The price is CA $164 per night from Mar 30 to Mar 31
CA $164
CA $188 total
Mar 30 - Mar 31
includes taxes & fees
Cambria Hotel New Haven University Area
See all 1,060 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.