Thimble Islands Adventure Vacations

Book a Adventure Hotel + Flight or Car together to unlock savings

Top Adventure vacation packages in Thimble Islands

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

Dolce by Wyndham Parsippany

Save 100% on your flight

$329

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

8.2/10 Very Good! (1,000 reviews)

Beechmont - Perfect for Family Retreat!

North End

$1,097

per person

Dec 8 - Dec 11

found 10 hours ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

No reviews

33 Hotel, New York City, Seaport

Manhattan

Save 100% on your flight

$1,548

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,003 reviews)

Such a wonderful hotel. The staff members were super helpful, fun, and made you feel at home immediately. Highly recommend the food as well!

Reviewed on Oct 24, 2026

Hotel Riu Plaza New York Times Square

Manhattan

Save 100% on your flight

$981

per person

Dec 26 - Dec 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (3,435 reviews)

We were expecting a much better room. The room seems outdated, the bedding was really uncomfortable and not cozy. Pillows were uncomfortable and we have to ask for more pillows. The sofa bed where my son slept, was dirty and we had to ask for additional clean sheets and blankets. The hallways looked like a hospital and just felt not cozy at all. The staff is amazing and very friendly.

Reviewed on Oct 23, 2026

The St. Regis New York

Manhattan

$2,162

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (293 reviews)

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5* Adventure vacations in Thimble Islands

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

Beechmont - Perfect for Family Retreat!

North End

$1,097

per person

Dec 8 - Dec 11

found 10 hours ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

No reviews

33 Hotel, New York City, Seaport

Manhattan

Save 100% on your flight

$1,548

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,003 reviews)

Such a wonderful hotel. The staff members were super helpful, fun, and made you feel at home immediately. Highly recommend the food as well!

Reviewed on Oct 24, 2026

The St. Regis New York

Manhattan

$2,162

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (293 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Thimble Islands

View all trips

3 Night Adventure vacations in Thimble Islands

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

Park Lane New York

Manhattan

$942

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

8.4/10 Very Good! (1,813 reviews)

Beechmont - Perfect for Family Retreat!

North End

$1,097

per person

Dec 8 - Dec 11

found 10 hours ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

No reviews

The St. Regis New York

Manhattan

$2,162

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (293 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Thimble Islands

View all trips

4 Night Adventure vacations in Thimble Islands

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

Hotel Riu Plaza New York Times Square

Manhattan

$449

per person

Jan 15 - Jan 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (3,435 reviews)

Reviewed on Oct 23, 2026

INNSiDE by Meliá New York Nomad

Manhattan

$597

per person

Jan 9 - Jan 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9.2/10 Wonderful! (2,365 reviews)

1 Hotel Brooklyn Bridge

$2,519

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,007 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Thimble Islands

View all trips

How can I book the best Thimble Islands adventure trips?

Choose your own adventure in Thimble Islands, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Thimble Islands family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Thimble Islands. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Thimble Islands adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Thimble Islands adventure vacation for couples?

Book a Thimble Islands couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Thimble Islands?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Thimble Islands with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.