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.
Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was CA $890, price is now CA $888 per person
CA $888
per person
Dec 23 - Dec 27
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.2/10 Very good! (1,000 reviews)
It was convenient to town and shopping. Our air conditioner leaked all over the rug and it was soaking wet. Pillows were awful. We would not stay there again.

Reviewed on Nov 6, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,120, price is now CA $1,858 per person
CA $1,858
per person
Dec 14 - Dec 17
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
No reviews

The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
Price was CA $1,262, price is now CA $1,118 per person
CA $1,118
per person
Dec 24 - Dec 30
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (227 reviews)

Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
Price was CA $1,809, price is now CA $1,765 per person
CA $1,765
per person
Dec 27 - Jan 2
found 4 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to New Haven (HVN)
6.6/10 (1,057 reviews)

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 $512 per night from Nov 29 to Nov 30
CA $512
CA $702 total
Nov 29 - Nov 30
includes taxes & fees
Gurney's Montauk Resort & Seawater Spa
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is CA $146 per night from Nov 18 to Nov 19
CA $146
CA $202 total
Nov 18 - Nov 19
includes taxes & fees
The Atlantic Hotel
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is CA $192 per night from Nov 17 to Nov 18
CA $192
CA $220 total
Nov 17 - Nov 18
includes taxes & fees
9.2/10 Wonderful! (446 reviews)
"Clean room"

Reviewed on Nov 9, 2026

Zey Hotel
See all 3,852 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.
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Stay near popular Water Mill attractions

A sign for the Parrish Art Museum surrounded by a white fence and greenery.

Parrish Art Museum

9.0/10 (9 reviews)
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.
See properties

What to do in Water Mill

Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,833
per traveller
The Hamptons and Long Island Wineries Private Tour
Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

CA $1,837
per traveller
100% of travellers recommend
Hamptons Private Day Trip from New York City
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 $888 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.