Water Mill holiday homes

We found 2,476 holiday rentals — enter your dates for availability
Discover a selection of 117 homes and other holiday rentals in Water Mill that are perfect for your trip. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Water Mill

Showing deals for:6 Nov - 13 Nov

Heated pool with gorgeous water and natural wetland view
A perfect get-away water front House in Southampton.
Main Entrance
Back view: Two story decks and large swimming pool
Exceptional
(35 reviews)

Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!

Southampton

8% off
NZ$14,777
for 7 nights, 1 home
NZ$2,111 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Pool
Pool
Outdoor dining
Pool
Exceptional
(5 reviews)

Newly Built Hamptons House, Pool, Beach Access + Easy Access of Montauk Highway

Hampton Bays

8% off
NZ$17,242
for 7 nights, 1 home
NZ$2,463 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access of Montauk Highway
private tennis court, decoturf
aerial view
view from living room towards pool, outdoor dining
gym with treadmill, cross trainer, weight machine, peloton, boxing bag
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
NZ$98,615
for 7 nights, 1 home
NZ$14,088 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Dining
Exterior
Patio
Living Room
Exceptional
(97 reviews)

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Sag Harbor

15% off
NZ$14,909
for 7 nights, 1 home
NZ$2,130 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Open Concept for Entertaining
Exterior
Exterior
Open Concept for Entertaining with a large dining table
Exceptional
(11 reviews)

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold

8% off
NZ$16,871
for 7 nights, 1 home
NZ$2,410 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
stunning  serenity
Private pool
Living area
Canoe or walk on trail to stunning lake beach.  Canoe and kayaks included.
Exceptional
(26 reviews)

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Southampton

30% off
NZ$17,237
for 7 nights, 1 home
NZ$2,462 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Room
Pool
Interior
Living area
Exceptional
(8 reviews)

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Water Mill

8% off
NZ$66,376
for 7 nights, 1 home
NZ$9,482 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Exterior
Pool
Dining
Dining
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
NZ$37,186
for 7 nights, 1 home
NZ$5,312 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Landscaped front entrance
Frankel Residence
Winding tree lined drive into property
Landscaped front entrance
Exceptional
(6 reviews)

Completely Renovated Home on ~2 Private Acres, Near Beach/Town

Wainscott

8% off
NZ$28,274
for 7 nights, 1 home
NZ$4,039 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Pool
Pool Area
Pool Terrace w/ Firepit
Screened Porch
Exceptional
(46 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
NZ$22,794
for 7 nights, 1 home
NZ$3,256 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Lounge on the daybed to take a break from swimming or watch the stars at night
Dine al fresco while watching the boats and sea planes
Enjoy the view while you swim!
Enjoy a heated swim or have a drink and soak on the martini ledge
Exceptional
(16 reviews)

Relax and Enjoy!

Shelter Island Heights

7% off
NZ$12,498
for 7 nights, 1 home
NZ$1,785 per night
includes taxes & fees
Relax and Enjoy!
Exterior
Pool
Outdoor dining
Exterior
Exceptional
(60 reviews)

Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool

Southampton

8% off
NZ$24,011
for 7 nights, 1 home
NZ$3,430 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Terrace/patio
Large deck with  sectional in the shade for cooling off. Fenced in pool for kids
Pool
Children’s area
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
NZ$14,394
for 7 nights, 1 home
NZ$2,056 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Dining
Property grounds
Pool
Pool
Exceptional
(10 reviews)

Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL

Sag Harbor

8% off
NZ$24,956
for 7 nights, 1 cottage
NZ$3,565 per night
includes taxes & fees
Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL
Large lush yard and patio.
Large lush backyard
Fully illuminated patio
Fully furnished patio, grill, outdoor shower
Exceptional
(24 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
NZ$12,419
for 7 nights, 1 home
NZ$1,774 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Pool Views
Pool
Living area
Access To Peconic Bay Views and sitting area directly across the street
Exceptional
(30 reviews)

North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk

Laurel

9% off
NZ$4,946
for 7 nights, 1 home
NZ$707 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
Beach
Living area
Exterior
Beach
Exceptional
(14 reviews)

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold

8% off
NZ$7,863
for 7 nights, 1 home
NZ$1,123 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Bathroom
Exterior
Off the master bedroom deck
Master bedroom with 10 foot electric fireplace
Exceptional
(27 reviews)

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub

Sag Harbor

8% off
NZ$24,828
for 7 nights, 1 home
NZ$3,547 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
living area with gas fire leads onto the deck
huge swimming pool and deck surrounded by trees
4 sun loungers on raised deck
living area and two bedrooms lead directly on to the pool
Exceptional
(53 reviews)

Large heated pool, games room, private bay beach access, gardens, kid-friendly

East Hampton

8% off
NZ$8,749
for 7 nights, 1 home
NZ$1,250 per night
includes taxes & fees
Large heated pool, games room, private bay beach access, gardens, kid-friendly
Living area
Private kitchen
Exterior
Private kitchen
Exceptional
(34 reviews)

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue

7% off
NZ$4,663
for 7 nights, 1 cottage
NZ$666 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Exterior detail
Private kitchen
Exterior
Exterior
Exceptional
(19 reviews)

Entire, new, roomy, village beach house close to beach, park, and town center

Greenport

8% off
NZ$8,127
for 7 nights, 1 home
NZ$1,161 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Living room on main floor with mid-century modern sofa
Privacy and luxury in the heart of East Hampton Village!
Spacious, light-filled five bedroom, four 1/2 bath within a walk to everything.
Sunlit living room w/ coffered ceilings, tv, fireplace, & French doors to pool
Exceptional
(18 reviews)

Prime East Hampton Village Location. Heated Pool. Walk To All!

East Hampton

15% off
NZ$13,128
for 7 nights, 1 home
NZ$1,875 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
view of pool
outdoor dining area
Pool
view of dining area on deck, amazing vista of farm fields
Exceptional
(15 reviews)

Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach

Water Mill

8% off
NZ$28,534
for 7 nights, 1 home
NZ$4,076 per night
includes taxes & fees
Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach
Dining
Pool
Living area
Private kitchen
Exceptional
(27 reviews)

Heated Pool + Hot Tub - Luxe 7BR Villa

Hampton Bays

9% off
NZ$15,850
for 7 nights, 1 home
NZ$2,264 per night
includes taxes & fees
Heated Pool + Hot Tub - Luxe 7BR Villa
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Luxury Water Mill will entice you

Take a holiday to Water Mill and enjoy the area's theatre scene, live music and art galleries. This city is well-known for its island views and wineries. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Water Mill

Are you searching for things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Water Mill a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Duck Walk Vineyards (1.4 mi / 2.3 km)
  • Wolffer Estates Vineyard (4.1 mi / 6.6 km)
  • Shinnecock Hills Golf Course (5.1 mi / 8.2 km)
  • LongHouse Reserve (9 mi / 14.4 km)
  • Peconic Bay Winery (9.8 mi / 15.7 km)
  • Bedell Cellars (9.9 mi / 15.9 km)

Exploring the natural landscape of Water Mill

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Water Mill. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • The Hamptons Beaches (2.4 mi / 3.9 km)
  • Cooper's Beach (4.8 mi / 7.8 km)
  • Elizabeth A. Morton National Wildlife Refuge (5 mi / 8 km)
  • Georgica Beach (7 mi / 11.3 km)
  • Meschutt Beach (8.1 mi / 13.1 km)
  • Shinnecock East County Park (8.2 mi / 13.1 km)

Transport options to and around Water Mill

The nearest airport is in East Hampton, NY (HTO), located 6 mi (9.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Westhampton, NY (FOK-Francis S. Gabreski), which is 16.2 mi (26 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Water Mill?
Based on our data, houses are the most sought-after type of holiday property in Water Mill. But as you might expect, everyone's idea of an epic stay can vary. Bookabach has holiday homes in a variety of shapes and sizes, and we'll help you discover the perfect match.
How much does it cost to rent a holiday home in Water Mill?
Different factors can determine how much you'll pay for a holiday home in Water Mill, like the time of year, property type and length of stay. But, all our holiday homes have something in common — excellent value. Simply enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Water Mill?
The average price for a holiday home near the beach in Water Mill depends on when you're travelling and the type and size of property you want. Find prices quickly and easily on Bookabach by entering the dates you'll be travelling. Then use the filter tool to pick the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Water Mill?
With 103 holiday homes that welcome four-legged guests, your furry friend can join in the fun on your Water Mill holiday. Use our filter tool to search our pet-friendly holiday homes and find your pawfect pad on Bookabach.
Can I rent a house with a pool in Water Mill?
Add another level of fun to your holiday by booking your group into one of the 93 houses with a private pool in Water Mill. Use our handy search filter to find the kind of property you want on Bookabach, and then spend your downtime frolicking in a swimming pool that's all your own.
What are popular home amenities in Water Mill?
When it comes to home amenities that guests are on the lookout for in Water Mill, a nearby waterfront, a sauna and tennis rank highest. With Bookabach holiday homes, you'll discover options to fit your taste and style, whether you're going on a trip with your partner, your friends or even pets.
Are there large group holiday homes in Water Mill?
Water Mill has 43 holiday homes that can cater to 10 or more guests. These properties come with the space you need to share good times with friends and family.
Are there holiday homes in Water Mill that welcome kids?
Bring the entire group together for a fun-packed adventure in Water Mill at one of our 102 family-friendly holiday homes. These stays feature amenities that are great for trips with the kids, like laundry facilities, extra bedrooms and swimming pools. Simply check the "Properties good for families" filter and pick your favourite.
What are the top attractions for families in Water Mill?
Keep the kids occupied at these fun family-friendly attractions in Water Mill:
  • Coopers Beach
  • The Hamptons Beaches
  • East Hampton Main Beach
Are there one-bedroom holiday homes in Water Mill?
There are two one-bedroom properties in Water Mill to pick from. A one-bedroom holiday property is an excellent option if it's just the two of you or if you're flying solo. Toss in more convenience, privacy and space compared to a hotel, and you'll be sure to have an unforgettable break.
Can I find two-bedroom holiday homes in Water Mill?
Pick from three two-bedroom holiday homes in Water Mill. Give your little ones the second room or maybe fill it with a couple of your besties. There's enough space for whoever's lucky enough to be joining your journey.
Are there holiday homes with WiFi in Water Mill?
Water Mill has 41 holiday homes with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to checking emails, these Bookabach homes make it easy to go online.
How can I find holiday homes with air conditioning in Water Mill?
You'll find 97 holiday homes with air conditioning in Water Mill offering that cooling breeze and extra level of comfort. Enter your dates of travel and then take advantage of our filter tool to find stays with air conditioning.
How old do you have to be to rent a holiday home in Water Mill?
The minimum age can differ between properties on Bookabach, so be sure to check the rules of the holiday home in Water Mill you want. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Water Mill for?
How long you can book a holiday home in Water Mill is down to the property. Simply enter your desired travel dates to see a list of options offering extended stays. With many amenities such as full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get a perfect place to call your home away from home in Water Mill.

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