Thimble Islands Beach Vacations

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Flight and Beach hotel deals in Thimble Islands

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

Radio Hotel

Manhattan

CA $830

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.6/10 Excellent! (2,506 reviews)

The complimentary drink vouchers and snacks. Close to the train station. The location is a little loud but that’s all NYC. There’s not a lot restaurant choices around but the restaurant on site is always an option. Overall you get what you pay for…

Reviewed on Aug 6, 2026

The Wall Street Hotel

Manhattan

CA $2,430

per person

Oct 9 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.6/10 Exceptional! (726 reviews)

1 Hotel Brooklyn Bridge

CA $2,556

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

The suite I got was unbelievable , best view ever from Brooklyn bridge . The service , the staff , everything perfect . Just the roof & pool and the is nothing crazy, honest , is very little , . Few chairs lit bit disappointed from the one in Miami . …

Reviewed on Aug 6, 2026

1 Hotel Central Park

Manhattan

CA $2,796

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,004 reviews)

Hotel Riu Plaza Manhattan Times Square

Manhattan

CA $1,509

per person

Oct 12 - Oct 16

found 2 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9.2/10 Wonderful! (3,822 reviews)

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5* Beach holidays in Thimble Islands

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

The Wall Street Hotel

Manhattan

CA $2,430

per person

Oct 9 - Oct 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.6/10 Exceptional! (726 reviews)

1 Hotel Brooklyn Bridge

CA $2,556

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

Reviewed on Aug 6, 2026

1 Hotel Central Park

Manhattan

CA $2,796

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,004 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Thimble Islands

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3 Night Beach holidays in Thimble Islands

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

Radio Hotel

Manhattan

CA $830

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.6/10 Excellent! (2,506 reviews)

Reviewed on Aug 6, 2026

1 Hotel Brooklyn Bridge

CA $2,556

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9/10 Wonderful! (1,002 reviews)

Reviewed on Aug 6, 2026

Hotel Riu Plaza Manhattan Times Square

Manhattan

CA $1,444

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (3,822 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Thimble Islands

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4 Night Beach holidays in Thimble Islands

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

Radio Hotel

Manhattan

CA $1,082

per person

Sep 22 - Sep 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

8.6/10 Excellent! (2,506 reviews)

Reviewed on Aug 6, 2026

Hotel Riu Plaza New York Times Square

Manhattan

CA $1,672

per person

Oct 9 - Oct 13

just found

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9/10 Wonderful! (3,255 reviews)

Good AC for the summer months Rooms on upper floors have great views although small . Don’t like the tacked on $33 resort fee ( for what ?). Location on 8th Ave can be sketchy at times. The included breakfast was fine but be prepared for huge crowds in the mornings-

Reviewed on Aug 6, 2026

The Wall Street Hotel

Manhattan

CA $2,329

per person

Oct 25 - Oct 29

found 18 hours ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.6/10 Exceptional! (726 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Thimble Islands

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What are some benefits when booking beach vacations in Thimble Islands?

When you travel to the beach in Thimble Islands, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

How can I book the best beach vacations in Thimble Islands?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Thimble Islands trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Thimble Islands?

There are quite a few things you can do to get cheap beach vacations in Thimble Islands. Prices range from CA $830, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Thimble Islands. These package deals let you save by booking your accommodation and your flight together with savings of up to 44.

Why should I book family beach vacations?

When you're travelling with the family to Thimble Islands, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Thimble Islands?

It's easy to find a beachfront vacation accommodation in Thimble Islands using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Thimble Islands as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Thimble Islands is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Connecticut. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in Thimble Islands

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Branford CT

16 min walk from Stony Creek - Thimble Islands Historic District

Book a stay at this family-friendly vacation home in Branford. Enjoy breakfast (surcharge), a garden, and concierge services. Popular attractions Stony Creek ...

See all 1,096 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.