Water Mill Holiday Rentals

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Holiday Rentals in Water Mill

Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (244)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in. "
United States
dean
The price is AU$459
includes taxes & fees
3 Nov - 4 Nov
Cliffside Resort Condominiums
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (300)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
Windward Shores Ocean Resort
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place to stay for small family "
United States
DongHo
The price is AU$304
includes taxes & fees
23 Oct - 24 Oct
Driftwood Resort
The SandPiper
9.8 out of 10, Exceptional, (27)
"My wife and I stayed at the Sandpiper for a long weekend. The property was very clean with a warm welcoming feeling. It is within walking distance to the beach and downtown shopping. Great location. I would recommend it to everyone."
United States
steve
The SandPiper
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
8.8 out of 10, Excellent, (28)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
United States
Allie G.
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
10.0 out of 10, Exceptional, (192)
"House was more then I can imagine , host was great , house literally have anything you forgot at home . "
United States
Isiah L.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
United States
James S.
The price is AU$582
includes taxes & fees
28 Oct - 29 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (141)
"Perfect property to hangout and stay entertained for hours"
United States
Ryder I.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
9.8 out of 10, Exceptional, (32)
"Wonderful outdoor space and great pool. Host was responsive and property was close to all things needed and wanted! Great rental for families."
United States
Patricia Fox M.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
10.0 out of 10, Exceptional, (95)
"We loved our stay - it was nice to be a short walk away from the bay and the pool was great. The home was very clean and comfortable."
United States
Katie C.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
8.4 out of 10, Very good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
United States
Riyao
The price is AU$1,416
includes taxes & fees
3 Nov - 4 Nov
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Work and Play Special! Extended Stay Discount
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is AU$2,073
includes taxes & fees
5 Nov - 6 Nov
Work and Play Special! Extended Stay Discount
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
United States
Kilee B.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
9.4 out of 10, Exceptional, (73)
"As always everything was excellent, This is our third stay at this property and we are booked for 2026"
United States
Michael R.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (76)
"It was a beautiful cottage on a gorgeous property with gracious hosts. I recommend it!!!!"
United States
Lisa
Fairy Tale Guest Cottage in Magic Garden by Pool
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
8.0 out of 10, Very good, (3)
"Great location and comfortable stay, amazing sheets.Ended up buying for my home. "
United States
David Y.
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
Summer getaway
9.0 out of 10, Wonderful, (14)
"Perfect location for a family holiday "
Germany
Olaf U.
Summer getaway
Cottage on Beach front Estate with Dockage .Walk to Village
10.0 out of 10, Exceptional, (71)
"Wonderful stay at such a special spot. "
United States
Meg B.
Cottage on Beach front Estate with Dockage .Walk to Village
American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
The price is AU$458
includes taxes & fees
26 Oct - 27 Oct
American Beech in Greenport - Petite King Room 7
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!
9.8 out of 10, Exceptional, (18)
"We had a wonderful stay here with our family. Great location, right on the beach, looking forward to returning!"
United States
Kyle D.
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!
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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Top Water Mill Hotel Reviews

Find out more about Water Mill

Everything you need to know about Water Mill holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Water Mill holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Water Mill holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Water Mill holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Water Mill. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Water Mill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Water Mill holiday rentals we have selected for you start as low as AU$304 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Water Mill rentals

At Expedia, we put the best Water Mill holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Water Mill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Water Mill holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Water Mill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Water Mill?

Yes, there are holiday rentals close to the most popular sights in Water Mill, or you can select a more secluded option if you're looking for a relaxing stay. Water Mill is known for its theatres and live music. Make sure you have time to check out the art and wineries during your trip.

What are some of the best holiday rentals that Water Mill has to offer?

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available : This holiday home rental outside of Water Mill is located near the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Water Mill?

Expedia has 113 holiday rentals for your stay in Water Mill.

What can I see and do in Water Mill?

Cultural attractions include Parrish Art Museum, whereas Mecox Bay is a spot to enjoy nature. Duck Walk Vineyards and Atlantic Golf Course are other places to visit while you're in town.

What are holiday rentals like in Water Mill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Water Mill. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.