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.
Three Ducks

Three Ducks

2 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Westhampton (FOK)
10/10 Exceptional! (1 review)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 25 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
The hotel and the overall experience exceeded all expectations.

Reviewed on Jul. 9, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very Good! (531 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 17 - Sep 24
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New York (JFK)
7.6/10 Good! (803 reviews)
Simple nice and clean

Reviewed on Jul. 11, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 17 - Sep 24
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New York (JFK)
7.8/10 Good! (1,467 reviews)
Beautiful hotel . Clean friendly. The pool area is amazing. I highly recommend.

Reviewed on Jul. 6, 2025

Ready to book your vacation to Water Mill?

 

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Water Mill Hotel Deals

Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
The price is CA $1,158 per night from Jul 30 to Jul 31
CA $1,158
CA $1,581 total
Jul 30 - Jul 31
includes taxes & fees
8.2/10 Very Good! (642 reviews)
"We were able to check in early. Nice staff"

Reviewed on Jun. 23, 2025

Gurney's Montauk Resort & Seawater Spa
Greenview Inn Riverhead
Greenview Inn Riverhead
2 out of 5
1433 W Main St, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jul 13 to Jul 14
CA $175
CA $200 total
Jul 13 - Jul 14
includes taxes & fees
6.8/10 (622 reviews)
"much improved inn from 2 years ago"

Reviewed on Jul. 8, 2025

Greenview Inn Riverhead
Hotel Indigo East End by IHG
Hotel Indigo East End by IHG
3.5 out of 5
1830 W Main St, Riverhead, NY
Fully refundable
The price is CA $327 per night from Aug 11 to Aug 12
CA $327
CA $373 total
Aug 11 - Aug 12
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Excellent service and good vibes! Very friendly staff and clean facilities."

Reviewed on Jul. 10, 2025

Hotel Indigo East End by IHG
See all 4,065 properties in Water Mill
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Water Mill

Parrish Art Museum

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.

Parrish Art Museum

What to do in Water Mill

East Hampton Shops

Hamptons Private Day Trip from New York City

CA $1,778
per traveller
Hamptons Private Day Trip from New York City
Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

CA $218
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,774
per traveller
The Hamptons and Long Island Wineries Private Tour
See all activities in Water Mill

Frequently asked questions

How much does a Water Mill vacation package cost?
Offering excellent value package deals from CA $821 on Expedia, you'll be surprised at how little a vacation to Water Mill costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Water Mill?
January, February and March are the best times to look for cheap Water Mill vacation packages. Choosing to travel in less busy periods means you can generally find lower prices on flights and accommodations.
How many days is enough for Water Mill?
With about 3 days, you'll have enough time to visit popular neighbourhoods like Village of Southampton and Wainscott Woods during your Water Mill vacation. Be sure to also add Shinnecock Hills Golf Course and Duck Walk Vineyards to your must-do list. In the mood for more adventures? Consider exploring outside of Water Mill on tours and day trips.
How to find the best Water Mill package deals?
Landing a cheap Water Mill package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most economical Water Mill package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Water Mill vacation as a package?
You can enjoy significant savings on your next Water Mill retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Water Mill?
If you have your Water Mill travel dates locked in, book as early as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Water Mill?

  1. Pick your dates: The things you'd like to do in Water Mill and your favourite season can help you decide when to go.
  2. Set your budget: Consider expenses like transportation, flights and meals when calculating how much to save for your trip to Water Mill. Then, pick a hotel that works with your budget, whether that's a low-cost stay or a high-end retreat.
  3. Decide how long to go away for: Now that you know more about Water Mill, you can figure out the ideal length of your vacation. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodations: After you've settled on your travel dates and duration, lock in the perfect Water Mill vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.