Water Mill Vacation Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Water Mill

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (274)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is CA $191
CA $249 total
includes taxes & fees
Mar 10 - Mar 11
Windward Shores Ocean Resort

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (214)
"We were visiting our so. And just needed an inexpensive..relatively..place to stay….. this was quite convenient…. We had a good night sleep…took a walk to beach..had a great chat with one of the ‘beach boys’ and thought it was lovely……"
Driftwood Resort

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is CA $251
CA $349 total
includes taxes & fees
Mar 30 - Mar 31
Cliffside Resort Condominiums

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (168)
"We had a wonderful stay. The house was great and check in and check out were both easy. We definition would love to stay again."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.4 out of 10, Good, (3)
"I had so much fun with my friends"
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (19)
"My friends and I stayed at this house for a few days around New Year's. The house is very spacious, and the grounds are lovely. We had a group of 5 and had lots of room to congregate and disappear if we needed alone time. The hot tub was exactly what some of us needed, while the kitchen provided others with much comfort. The one bummer was when we arrived; it looked like someone had just had a party outside so that first made for a bit of cleanup. That little bump shouldn't stop you from...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

East Hampton Paradise – Cozy 5BR, Pool & Walkable to Beach & Shops

2.0 star property
East Hampton Paradise – Cozy 5BR, Pool & Walkable to Beach & Shops

Sprawling Southampton Home: Private Pool

9.0 out of 10, Wonderful, (44)
"My family and I had a wonderful stay at this property. The house was well-situated in a quiet neighborhood - very private, surrounded by trees and a few wild turkeys. There were many amenities that made our stay enjoyable from the large patio and pool, 3 full baths in the main house, one of which had an amazing shower system with body spray, and a designated work area for those that can’t leave work behind. Communication with the property manager was easy and Debbie was very helpful and...
Sprawling Southampton Home: Private Pool

Summer getaway

9.2 out of 10, Wonderful, (10)
"Overall, we had a terrific time at the house. Thank-you so much Andres for sharing your home with us. Getting there, checking in, all simple and easy. House was very well stocked. There was plenty of room for the eight of us. The beds were all comfortable. The deck was delightful. A couple of minor things that we had happen, or noticed that might want to be addressed. Given the house is controlled by Alexa, some detailed instructions as to how to work with "her" might be a good idea for...
Summer getaway

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

10.0 out of 10, Exceptional, (98)
"Pam was very communicative prior to our stay and a welcoming host. The house was clean, centrally located, and spacious. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Summer 2025 Now Available! Wolffer Vineyard Close!

10.0 out of 10, Exceptional, (83)
"Our stay was amazing! The house was fabulous, beautifully appointed, very clean, private and secluded. Lots to do in the area. Jay was very responsive and helpful when we had questions. Would definitely stay again. "
Summer 2025 Now Available! Wolffer Vineyard Close!

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (64)
"We had an incredible time at this house!!! It literally felt like we were staying at a luxury resort and had everything we could have possibly needed for our getaway. Our group included young kids and adults all of whom had an amazing stay. The tennis and basketball court was in great condition and provided endless fun activities. The pool was a great size and the heater worked well when it was needed. There is a ton of space to play sports and games as well as a fire pit which was a great way...
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

10.0 out of 10, Exceptional, (29)
"We enjoyed a year end visit at Jean Marc's beautiful home. There were incredible water views from the floor to ceiling windows in the living room and the master bedroom. The house was clean, comfortable and well furnished. In particular, the kitchen was stocked with everything you need for preparing family meals. Jean Marc was a very responsive and accommodative host!"
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (5)
"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"
The price is CA $723
CA $1,362 total
includes taxes & fees
Mar 20 - Mar 21
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

9.6 out of 10, Exceptional, (15)
"The property was absolutely stunning! Very accommodating with many rooms for us all and the yard/ grounds were beautiful. Very modern and stylish interior yet cozy and inviting. Will definitely be keeping in mind for our next trip! "
Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (7)
"Great bungalow for weekend getaway. New building with spacious shower and access to pool and hot tub. In a very quiet area of Bridgehampton with close access to restaurants and shopping. Host was very responsive and helpful. "
The price is CA $282
CA $546 total
includes taxes & fees
Mar 5 - Mar 6
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (128)
"Wonderful throw back beach house..nothing fancy but very comfortable and the views are amazing! Loved spending our Christmas Holiday relaxing by the bay..and the year round hot tub was up and running when we got there! Perfect spot..will definitely go back next year! "
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
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.
Don't see what you're looking for?
See all available properties in Water Mill
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Water Mill you may be interested in

Hyatt Place Long Island East End

3.0 star property
9.2 out of 10, Wonderful, (1007)
"View from the room was beautiful "
The price is CA $149
CA $171 total
includes taxes & fees
Mar 16 - Mar 17
Hyatt Place Long Island East End

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very good, (612)
"It’s under construction so it’s not as nice as I typically would be. I wishes we had been warned . Although the staff is friendly and helpful"
The price is CA $413
CA $564 total
includes taxes & fees
Mar 24 - Mar 25
Gurney's Montauk Resort & Seawater Spa

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (212)
"Perfect get away "
The price is CA $254
CA $319 total
includes taxes & fees
Mar 18 - Mar 19
Baron's Cove
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.

Frequently asked questions

Can I find a vacation rental in Water Mill?

Yes, we have vacation rentals close to popular sights in Water Mill, or you can select a more remote option if you're looking for relaxation. Water Mill is known for its theaters and live music. Make sure you have time to check out the art and wineries during your trip.

What's the top vacation rental that Water Mill has to offer?

10 Bedroom Hampton House with a regulation size Pickleball: You might like this vacation home rental near Water Mill. It is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Water Mill?

Expedia has 97 vacation rentals for your stay in Water Mill.

What can I see and do in Water Mill?

The Hamptons Beaches and Mecox Bay are a couple of scenic spots to enjoy the outdoors, whereas Parrish Art Museum is one of the cultural attractions. Duck Walk Vineyards and Atlantic Golf Course are other places to visit while you're in town.

What are vacation rentals like in Water Mill?

Vacation rentals are private properties you can stay in for several days or longer in Water Mill. Vacation rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.