Water Mill Vacation Packages
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Your Water Mill Vacation
Say goodbye to the worries of planning and hello to a Water Mill vacation package. With your travel details organized before you take off, you can focus on discovering the best of this city, starting with Village of Southampton, which is good for history, coastal beaches and culture. If taking in sights is on the to-do list during your trip to Water Mill, look around popular attractions like Coopers Beach, Wolffer Estates Vineyard and Shinnecock Nation Cultural Center and Museum. Whoever you're heading away with and whatever your budget, your dream Water Mill vacation is just a few clicks away with Expedia.
Top Water Mill Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Loews Regency New York Hotel
Manhattan
Price was CA $3,110, price is now CA $1,845 per person
CA $1,845
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Staff were very accomodating and looked after my family well during our stay. Nothing was too difficult for them.
Reviewed on Jan 17, 2026
1 Hotel Central Park
Manhattan
Price was CA $3,267, price is now CA $2,010 per person
CA $2,010
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby.
Reviewed on Feb 2, 2026
The Fifth Avenue Hotel
Manhattan
Price was CA $3,505, price is now CA $2,194 per person
CA $2,194
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (159 reviews)
Staff were lovely, helpful and pleasant. Turndown service way too late, though—9:45 might catch some guests sleeping.
Reviewed on Jan 3, 2026
1 Hotel Brooklyn Bridge
Price was CA $4,579, price is now CA $3,003 per person
CA $3,003
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
The entire stay was exceptional! From the point of entry to departure 10/10
Reviewed on Jan 29, 2026
The Pierre, A Taj Hotel, New York
Manhattan
Price was CA $2,804, price is now CA $1,883 per person
CA $1,883
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (1,007 reviews)
Staff warm, & welcoming, bar, great breakfast, & restaurant lovely, don’t miss coffee at the bar in the morning & Friday with the Martinis piano singers.
Reviewed on Feb 5, 2026
Water Mill Hotel Deals
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is CA $427 per night from Feb 22 to Feb 23
CA $427
CA $586 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (722 reviews)
Room was spotless, staff were great and the resort is top notch!!
Reviewed on Feb 2, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
The price is CA $203 per night from Mar 10 to Mar 11
CA $203
CA $271 total
Mar 10 - Mar 11
includes taxes & fees
8.4/10 Very Good! (609 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...
Reviewed on Jan 10, 2026
Hilton Garden Inn Riverhead
2038 Old Country Rd Riverhead NY
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Feb 15 to Feb 16
CA $156
CA $178 total
Feb 15 - Feb 16
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
The amenities were great! Staff was amazing! Overall a great stay. Will be back soon!
Reviewed on Jan 24, 2026
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.
Discover the most popular places to visit in Water Mill
Parrish Art Museum
Browse the contemporary artwork displays, discover the talents of some the Hamptons best known artists and admire the barn-like design of this Long Island legend.
What to do in Water Mill
Hamptons Private Day Trip from New York City
CA $1,804
per traveller
The Hamptons and Long Island Wineries Private Tour
CA $1,804
per traveller
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
