Thimble Islands Pet-friendly Vacations

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Flight and Pet-friendly hotel deals in Thimble Islands

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

Manhattan
CA $908
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,493 reviews)
5th & 55th Residence Club

5th & 55th Residence Club

Manhattan
CA $3,504
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.4/10 Very good! (5 reviews)
NobleDEN Hotel

NobleDEN Hotel

Manhattan
CA $2,417
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.8/10 Exceptional! (1,634 reviews)
We love the NobleDen! Staff is really friendly. Rooms are clean and big and have been very reasonably priced both times we have stayed there. Great for a mother / teenage daughter weekend hangout. Will stay there again for absolute sure!!!

Reviewed on Aug 16, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

CA $2,895
per person
Sep 25 - Sep 28
found 7 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
Sound View Greenport

Sound View Greenport

CA $2,181
per person
Oct 19 - Oct 26
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very good! (675 reviews)
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5* Pet-friendly holidays in Thimble Islands

Price found within the past 48 hours. Click for updated prices.
The Chatwal, In The Unbound Collection By Hyatt

The Chatwal, In The Unbound Collection By Hyatt

Manhattan
CA $2,019
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (671 reviews)
5th & 55th Residence Club

5th & 55th Residence Club

Manhattan
CA $3,504
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.4/10 Very good! (5 reviews)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

CA $2,895
per person
Sep 25 - Sep 28
found 7 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
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3 Night Pet-friendly holidays in Thimble Islands

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

Manhattan
CA $908
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,493 reviews)
5th & 55th Residence Club

5th & 55th Residence Club

Manhattan
CA $3,504
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.4/10 Very good! (5 reviews)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

Manhattan
CA $1,435
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,268 reviews)
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4 Night Pet-friendly holidays in Thimble Islands

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

Manhattan
CA $1,124
per person
Oct 9 - Oct 13
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,493 reviews)
The St. Regis New York

The St. Regis New York

Manhattan
CA $4,275
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (288 reviews)
best

Reviewed on Jul 18, 2026

33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

Manhattan
CA $1,640
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,005 reviews)
When checking in the front desk informed me that I had $42 to spend in room order including patronage at the restaurant on site. They did not mention that the spend doesn’t include or cannot apply to gratuity. I spent $40 on the entire bill at the restaurant and the hotel only took off the portion without the gratuity. The toilet was not flushing well and toward the end of my stay the water never stopped running so I had to call the front desk at 10pm. The elevator was not working but the technician appeared to not communicate to hotel guests by just standing there. I had to carry 3 bags and took a few steps down to another elevator.

Reviewed on Aug 11, 2026

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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.