Thimble Islands Adventure Vacations

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Flight and Adventure hotel deals in Thimble Islands

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

Beechmont - Perfect for Family Retreat!

North End

CA $1,273

per person

Oct 16 - Oct 18

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to New Haven (HVN)

No reviews

Radio Hotel

Manhattan

CA $1,305

per person

Oct 13 - Oct 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.6/10 Excellent! (2,506 reviews)

Hotel Riu Plaza New York Times Square

Manhattan

CA $1,672

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9/10 Wonderful! (3,255 reviews)

Hotel Riu Plaza Manhattan Times Square

Manhattan

CA $1,509

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9.2/10 Wonderful! (3,841 reviews)

Great experience staying with family

Reviewed on Aug 8, 2026

1 Hotel Brooklyn Bridge

CA $3,000

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

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5* Adventure holidays in Thimble Islands

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

Beechmont - Perfect for Family Retreat!

North End

CA $1,273

per person

Oct 16 - Oct 18

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to New Haven (HVN)

No reviews

1 Hotel Brooklyn Bridge

CA $3,000

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

The Wall Street Hotel

Manhattan

CA $2,100

per person

Oct 8 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to New York (JFK)

9.6/10 Exceptional! (726 reviews)

Great service. What you’d expect from a five star hotel in NYC

Reviewed on Aug 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Thimble Islands

View all trips

3 Night Adventure holidays in Thimble Islands

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

Radio Hotel

Manhattan

CA $755

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.6/10 Excellent! (2,506 reviews)

1 Hotel Brooklyn Bridge

CA $2,324

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

The Wall Street Hotel

Manhattan

CA $1,461

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.6/10 Exceptional! (726 reviews)

Great service. What you’d expect from a five star hotel in NYC

Reviewed on Aug 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Thimble Islands

View all trips

4 Night Adventure holidays in Thimble Islands

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

Hotel Riu Plaza New York Times Square

Manhattan

CA $1,672

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9/10 Wonderful! (3,255 reviews)

Lotte New York Palace

Manhattan

CA $1,812

per person

Oct 25 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (2,167 reviews)

Poor customer service, I received no friendly response from any staff. Really disappointed has nothing to do with the NY Palace I used to stay decades ago. Won’t stay again.

Reviewed on Aug 7, 2026