Hamptons Adventure Vacations 2026

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Top Adventure vacation packages in Hamptons

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

Hero Beach Club

$929

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Miami (MIA) to New York (JFK)

9/10 Wonderful! (236 reviews)

Topping Rose House

Save 100% on your flight

$1,219

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Myrtle Beach (MYR) to New York (JFK)

9/10 Wonderful! (157 reviews)

Faraway Sag Harbor

$1,160

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Myrtle Beach (MYR) to New York (JFK)

9/10 Wonderful! (302 reviews)

Montauk Yacht Club

$1,367

per person

Oct 1 - Oct 4

found 15 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to New York (JFK)

8.6/10 Excellent! (1,013 reviews)

This was a beautiful property on the water. We went to celebrate a birthday and it was the perfect location. The bedrooms were large and had high end toiletries. The restaurants on the property were delicious and had excellent service. It's also pretty centrally located and was only a few minutes from the downtown area. Highly recommend this property.

Reviewed on Aug 31, 2026

The Maidstone

$1,314

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Myrtle Beach (MYR) to New York (JFK)

8.2/10 Very Good! (170 reviews)

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See all available trips from Columbus to Hamptons

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3 Night Adventure vacations in Hamptons

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

Faraway Sag Harbor

$808

per person

Nov 11 - Nov 14

found 16 hours ago

Roundtrip flight included

PBI (PBI) to New York (JFK)

9/10 Wonderful! (302 reviews)

Montauk Yacht Club

$1,367

per person

Oct 1 - Oct 4

found 15 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to New York (JFK)

8.6/10 Excellent! (1,013 reviews)

Reviewed on Aug 31, 2026

Topping Rose House

$2,378

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Houston (IAH) to New York (JFK)

9/10 Wonderful! (157 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Hamptons

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4 Night Adventure vacations in Hamptons

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

Daunt's Albatross Motel

Downtown Montauk

$742

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Myrtle Beach (MYR) to New York (JFK)

9/10 Wonderful! (321 reviews)

Topping Rose House

Save 100% on your flight

$1,219

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Myrtle Beach (MYR) to New York (JFK)

9/10 Wonderful! (157 reviews)

Faraway Sag Harbor

$1,160

per person

Nov 4 - Nov 8

found 1 day ago

Roundtrip flight included

Myrtle Beach (MYR) to New York (JFK)

9/10 Wonderful! (302 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Hamptons

View all trips

How can I book the best Hamptons adventure trips?

Choose your own adventure in Hamptons, 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 Hamptons family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Hamptons. 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 Hamptons 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 Hamptons adventure vacation for couples?

Book a Hamptons 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 Hamptons?

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 Hamptons 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.

Why should I book a Hamptons adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

Top Adventure Hamptons Hotels

Montauk Yacht Club

32 Star Island Rd Montauk NY

1 hour drive from The Hamptons Beaches

Book a stay at this luxury hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ...

8.6/10 Excellent! (1,003 reviews)

"This was a beautiful property on the water. We went to celebrate a birthday and it was the perfect location. The bedrooms were large and had high end toiletries. The restaurants on the property were delicious and had excellent service. It's also pretty centrally located and was only a few minutes ..."

Reviewed on Aug 31, 2026

434 on Main

434 Main Street Amagansett NY

29 min drive from The Hamptons Beaches

Stay at this B&B in Amagansett. Enjoy free breakfast, free WiFi, and free parking. Popular attractions East Hampton Main Beach and The Stephen Talkhouse are ...

Bayview Resort

53 West Tiana Road Hampton Bays NY

42 min drive from The Hamptons Beaches

Book a stay at this beach motel in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...

8.8/10 Excellent! (489 reviews)

"We had a wonderful stay at this beautiful resort. The location was great, a neutral spot for going to the north or south fork. The staff was so nice and welcomed us with a bottle of wine for our anniversary. The went out of their way with little touches to make it an unforgettable stay."

Reviewed on Aug 31, 2026

See all 3,706 properties in Hamptons

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.