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.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
CA $780
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to New Haven (HVN)
8/10 Very good! (1,009 reviews)
It was a very nice hotel. The room was clean and comfortable, the staff was friendly, and the location was convenient. We had a great stay and really enjoyed our time there.
Reviewed on Aug 11, 2026
Head of Pond House
CA $2,904
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to New Haven (HVN)
10/10 Exceptional! (11 reviews)
My husband and I spent a weekend at this beautiful place and loved it! The house is super clean, well located and has a private feeling, with amazing views to a peaceful garden. Pauline’s customer service was great and really took care of us also letting us do a late check out. Strongly recommend you stay here during your trip to the Hamptons!
Reviewed on Jul 27, 2026
Ready to book your vacation to Water Mill?
Water Mill Hotel Deals
Sound View Greenport
58775 County Rd 48 Greenport NY
CA $384
CA $558 total
Sep 9 - Sep 10
includes taxes & fees
8.4/10 Very good! (685 reviews)
"I stayed in this hotel for one night only. Thank God. We checked in and left to hang out on downtown. Came back at late night and the AC unit made a loud noise every 5 mins . Couldn’t sleep. We were on the last building which is far distance from front desk. try to reach the front desk and the phone ..."
Reviewed on Aug 10, 2026
The Atlantic Hotel
1655 County Road 39 Southampton NY
CA $275
CA $349 total
Sep 8 - Sep 9
includes taxes & fees
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
CA $1,066
CA $1,462 total
Sep 10 - Sep 11
includes taxes & fees
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.
Stay near popular Water Mill attractions
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.
Duck Walk Vineyards
Sample award-winning wines and take some bottles home as souvenirs when you visit one of two beautiful vineyards that have become Long Island institutions.
Atlantic Golf Course
Enjoy a round of golf in Water Mill at Atlantic Golf Course. While you're in the area, stroll along the beautiful beaches.
The Watermill Center
The Watermill Center is just one of the places to see in Water Mill, so why not enjoy the other things to explore during your travels? Experience the area's theater scene and live music.
Mill Pond
Commune with nature and explore the great outdoors at Mill Pond during your travels in Water Mill. Experience the area's theater scene and live music.
What to do in Water Mill
The Hamptons and Long Island Wineries Private Tour
CA $1,824
per traveller
Hamptons Private Day Trip from New York City
CA $1,824
per traveller
100% of travellers recommend
Frequently asked questions
How much does a Water Mill vacation package cost?
Offering excellent value package deals from CA $780 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?
- Pick your dates: The things you'd like to do in Water Mill and your favourite season can help you decide when to go.
- 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.
- 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.
- 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.
