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.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was CA $1,261, price is now CA $802 per person
CA $802
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (6,263 reviews)
The staff was amazing!

Reviewed on Aug. 23, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,302, price is now CA $2,350 per person
CA $2,350
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,911, price is now CA $1,110 per person
CA $1,110
per person
Oct 26 - Oct 31
just found
Roundtrip flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug. 12, 2025

Staypineapple, An Artful Hotel, Midtown

Staypineapple, An Artful Hotel, Midtown

3 out of 5
Manhattan
Price was CA $1,720, price is now CA $1,055 per person
CA $1,055
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,037 reviews)
very friendly staff, water refill, good location although the particular street is not so nice,

Reviewed on Aug. 20, 2025

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was CA $1,361, price is now CA $863 per person
CA $863
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,466 reviews)
Beautiful view. Next to PATH train.

Reviewed on Aug. 22, 2025

Ready to book your vacation to Water Mill?

 

Choose your dates

Water Mill Hotel Deals

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 $157 per night from Sep 23 to Sep 24
CA $157
CA $180 total
Sep 23 - Sep 24
includes taxes & fees
7.2/10 Good! (702 reviews)
"Always my choice when staying in the area. Staff very friendly. Check in is quick and easy. Not to mention the newly renovated rooms."

Reviewed on Aug. 20, 2025

Greenview Inn Riverhead
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is CA $223 per night from Sep 21 to Sep 22
CA $223
CA $289 total
Sep 21 - Sep 22
includes taxes & fees
7/10 Good! (914 reviews)
"Nice place. Recommend."

Reviewed on Aug. 18, 2025

The Atlantic Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is CA $400 per night from Sep 9 to Sep 10
CA $400
CA $525 total
Sep 9 - Sep 10
includes taxes & fees
8.4/10 Very Good! (561 reviews)
"Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound"

Reviewed on Aug. 18, 2025

Sound View Greenport
See all 3,976 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
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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 $1,788
per traveller
Hamptons Private Day Trip from New York City
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

CA $191
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,788
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 $802 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.