Hamptons Adventure Vacations
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Top Adventure vacation packages in Hamptons
Price found within the past 48 hours. Click for updated prices.
Hero Beach Club
Save 100% on your flight
Price was $3,202, price is now $2,590 per person
$2,590
per person
Jul 1 - Jul 7
found 22 hours ago
Roundtrip flight included
Omaha (OMA) to New York (JFK)
9/10 Wonderful! (204 reviews)
The rooms were clean. The bathroom had a pocket door for the toilet area that did not close properly and the lock did not work. The shower was outside the toilet area, but there was no door only a curtain.
Reviewed on Mar 29, 2026
The Maidstone
Save 100% on your flight
Price was $10,415, price is now $6,404 per person
$6,404
per person
Jul 1 - Jul 7
found 22 hours ago
Roundtrip flight included
Omaha (OMA) to New York (JFK)
8/10 Very Good! (156 reviews)
Loved the property. Best of all, the night/weekend manager gave me his cell in case I needed anything when front desk was closed. They were also accommodating when snow storm affected my travel. I can’t wait to return!
Reviewed on Apr 6, 2026
Topping Rose House
Save 100% on your flight
Price was $3,531, price is now $2,637 per person
$2,637
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
George Town (GCM) to New York (JFK)
9/10 Wonderful! (149 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower.
But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker.
Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door.
It’s little odd things that just made it not feel like a luxury stay.
And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use.
The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.
Reviewed on Mar 24, 2026
3 Night Adventure vacations in Hamptons
Price found within the past 48 hours. Click for updated prices.
Hero Beach Club
Price was $1,367, price is now $1,107 per person
$1,107
per person
Jun 11 - Jun 14
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to New York (JFK)
9/10 Wonderful! (204 reviews)
The rooms were clean. The bathroom had a pocket door for the toilet area that did not close properly and the lock did not work. The shower was outside the toilet area, but there was no door only a curtain.
Reviewed on Mar 29, 2026
Topping Rose House
Price was $5,136, price is now $3,964 per person
$3,964
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (149 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower.
But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker.
Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door.
It’s little odd things that just made it not feel like a luxury stay.
And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use.
The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.
Reviewed on Mar 24, 2026
4 Night Adventure vacations in Hamptons
Price found within the past 48 hours. Click for updated prices.
The Maidstone
Save 100% on your flight
Price was $3,523, price is now $2,190 per person
$2,190
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
George Town (GCM) to New York (JFK)
8/10 Very Good! (156 reviews)
Loved the property. Best of all, the night/weekend manager gave me his cell in case I needed anything when front desk was closed. They were also accommodating when snow storm affected my travel. I can’t wait to return!
Reviewed on Apr 6, 2026
Topping Rose House
Save 100% on your flight
Price was $5,824, price is now $4,181 per person
$4,181
per person
Jul 9 - Jul 13
found 12 hours ago
Roundtrip flight included
Chicago (CHI) to New York (JFK)
9/10 Wonderful! (149 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower.
But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker.
Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door.
It’s little odd things that just made it not feel like a luxury stay.
And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use.
The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.
Reviewed on Mar 24, 2026
Find awesome Hamptons adventure vacations
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
Book a stay at this beach 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! (1,000 reviews)
The Montauk Yacht Club is a beautiful and relaxing getaway with a true coastal luxury feel. The property is well-maintained, with scenic waterfront views that make the entire experience feel special and refreshing. The rooms are comfortable and thoughtfully designed, offering a clean and modern aesthetic. ...
Reviewed on Apr 21, 2026
434 on Main
434 Main Street Amagansett NY
Stay at this B&B in Amagansett. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Amagansett Square and Amelia Cottage Museum are located ...
Bayview Resort
53 West Tiana Road Hampton Bays NY
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! (455 reviews)
Just right.
Reviewed on Nov 19, 2025
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.
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.
