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)
Sound View Greenport

Sound View Greenport

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

Pestana CR7 Times Square

Pestana CR7 Times Square

Manhattan
CA $2,186
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,013 reviews)
Black stuff growing in the shower. Toilet set was broken. Extremely load AC unit directly next to the bed making it near impossible to sleep. Stay elsewhere.

Reviewed on Aug 16, 2026

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5* Pet-friendly holidays in Thimble Islands

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

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 $2,730
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
Didn’t allow me to get late checkout . Upon arrival the valet wasn’t even outside to help with baggage , for such an expensive hotel , I’d say my expectations were completely unmet

Reviewed on Aug 16, 2026

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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)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

CA $2,895
per person
Sep 25 - Sep 28
found 16 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
Didn’t allow me to get late checkout . Upon arrival the valet wasn’t even outside to help with baggage , for such an expensive hotel , I’d say my expectations were completely unmet

Reviewed on Aug 16, 2026

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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 23 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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More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.