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.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
Price was CA $540, price is now CA $495 per person
CA $495
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.4/10 Very good! (834 reviews)
Good value

Reviewed on Jul 9, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,246, price is now CA $1,018 per person
CA $1,018
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $893, price is now CA $741 per person
CA $741
per person
Sep 4 - Sep 7
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8/10 Very good! (1,001 reviews)
The room was hot, and AC barely worked.

Reviewed on Jul 10, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,060, price is now CA $1,733 per person
CA $1,733
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
No reviews

Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was CA $710, price is now CA $627 per person
CA $627
per person
Sep 4 - Sep 7
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
7/10 Good! (931 reviews)
We got in and had to wait nearly half an hour with small kids for the receptionist to show up to check us in. Then I was bitten by bed bugs.

Reviewed on Jul 9, 2026

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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 $1,549 per night from Aug 10 to Aug 11
CA $1,549
CA $2,124 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very good! (820 reviews)
"-"

Reviewed on Jul 10, 2026

Gurney's Montauk Resort & Seawater Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is CA $757 per night from Aug 6 to Aug 7
CA $757
CA $986 total
Aug 6 - Aug 7
includes taxes & fees
8.4/10 Very good! (664 reviews)
"The staff was helpful and nice. The exterior of the property was fine and the landscaping pretty. However the room was awful - not particularly clean, a noisy, wall ac plugged in next to the bed, felt like a renovated motel room. Sorry not worth $700/ night."

Reviewed on Jul 8, 2026

Sound View Greenport
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is CA $355 per night from Jul 27 to Jul 28
CA $355
CA $441 total
Jul 27 - Jul 28
includes taxes & fees
7.2/10 Good! (1,003 reviews)
"Terrible!!!! We arrived at the Atlantic Inn at 5:00 pm after being on the beach all day only to be told that they cancelled our reservation for the 2 rooms we booked!!! They were so rude about it and didn’t even apologize. They tried running our credit card prior to arrival but unfortunately that ..."

Reviewed on Jul 5, 2026

The Atlantic Hotel
See all 3,994 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

An art gallery with a wooden ceiling and a long hallway displaying various artworks.

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

Hamptons Private Day Trip from New York City

Hamptons Private Day Trip from New York City

CA $1,845
per traveller
100% of travellers recommend
Hamptons Private Day Trip from New York City
Wine and grapes against the sea

The Hamptons and Long Island Wineries Private Tour

CA $1,845
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 $495 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.

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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.