Thimble Islands Vacation Packages

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Top Thimble Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wayne Inn

The Wayne Inn

2 out of 5
Price was CA $1,614, price is now CA $884 per person
CA $884
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
6.8/10 (291 reviews)
Clean room - hot shower -

Reviewed on May 5, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,237, price is now CA $1,990 per person
CA $1,990
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,004 reviews)
We love 1Hotel. This was our fourth visit. However, this visit was different. From the loud music playing until two oclock in the morning, to the garbage left behind outside the entrance to the nightclub, the vibe was not at all what we experienced previously during our trips to Brooklyn. We sincerely hope the decision to use the upstairs floor as a nightclub is reconsidered. Being kept awake by loud music is not acceptable. Also, there was a bag of trash sitting on top of the trashcan for two days.Such a shame for this beautiful hotel. Attention to detail is what made this hotel so special.

Reviewed on May 10, 2026

Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
Manhattan
Price was CA $1,685, price is now CA $1,042 per person
CA $1,042
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very Good! (6,856 reviews)
Rooms were not clean. Dusty floors, showers and fixtures like lamps and table ( I had a suite) . The couch in the suite was horrible. The shower was broken so I had to rig it to use it. They don’t have smart tvs! That is a must in 2026. For the money I expected better with cleanliness. Otherwise everything else was standard nothing exceptional

Reviewed on May 12, 2026

Heritage Hotel

Heritage Hotel

2.5 out of 5
Manhattan
Price was CA $1,791, price is now CA $1,171 per person
CA $1,171
per person
Jul 20 - Jul 24
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.2/10 Very Good! (1,753 reviews)
Neat clean & tidy, great location close to everything including subway stations and great eateries/bars. Great price and staff. Would stay again.

Reviewed on May 11, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,845, price is now CA $1,210 per person
CA $1,210
per person
Aug 5 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,003 reviews)
The hotel was nice, room was very clean, bed was comfortable. The mini-fridge in the room was purely a minibar with no room for storage (and the door was stuck when I tried to use it). I didn’t ask about this, but it’s something to mention that was unexpected.

Reviewed on May 8, 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 $173 per night from May 25 to May 26
CA $173
CA $199 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (2,141 reviews)
Great location. Staff is always friendly and attentive. This hotel is always great for our weekend stays near Yale campus.

Reviewed on May 11, 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
The price is CA $220 per night from Jun 7 to Jun 8
CA $220
CA $253 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,017 reviews)
Hotel was very nice staff was excellent especially checking in very helpful friendly

Reviewed on May 11, 2026

Omni New Haven Hotel at Yale
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 $104 per night from May 25 to May 26
CA $104
CA $120 total
May 25 - May 26
includes taxes & fees
6.4/10 (1,017 reviews)
Nice

Reviewed on May 10, 2026

Motel 6 Milford, CT
See all 1,091 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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