Water Mill holiday rentals

We found 2,430 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:25 Dec - 1 Jan

2nd floor deck with additional dining and leisure seating.
Dining table and picnic table water view
Chef kitchen with breakfast area on 2nd floor
Heated pool with gorgeous water and natural wetland view
Exceptional
(38 reviews)

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

Southampton

5% off
AU$20,478
for 7 nights, 1 home
AU$2,925 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Pool
Pool
Terrace/patio
Outdoor dining
Exceptional
(6 reviews)

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

Hampton Bays

8% off
AU$14,256
for 7 nights, 1 home
AU$2,037 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
Patio
Private kitchen
Exterior
Dining Room
Exceptional
(103 reviews)

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

Sag Harbor

16% off
AU$11,937
for 7 nights, 1 home
AU$1,705 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
kitchen with large island and breakfast table
aerial view
master bedroom with balcony
living room
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
AU$81,196
for 7 nights, 1 home
AU$11,599 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Living area
Terrace/patio
Living area
Pool
Excellent
(10 reviews)

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

Water Mill

8% off
AU$54,651
for 7 nights, 1 home
AU$7,807 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Exterior
Pool
Outdoor dining
Dining Room with seating for Ten
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
AU$11,945
for 7 nights, 1 home
AU$1,706 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Large Dining/Kitchen Space
Exterior
Exterior
Spacious Main Floor Living room
Exceptional
(11 reviews)

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

Southold

8% off
AU$17,468
for 7 nights, 1 home
AU$2,495 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Den
Pool
New Kitchen
Living room w/ screen porch beyond
Exceptional
(48 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
AU$18,739
for 7 nights, 1 home
AU$2,677 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Living area
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining +10,)
park-like grounds
Exceptional
(26 reviews)

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

Southampton

30% off
AU$14,252
for 7 nights, 1 home
AU$2,036 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Outdoor dining
Living area
Pool
Interior
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
AU$10,676
for 7 nights, 1 home
AU$1,525 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Living area
Outdoor dining
Exterior
More vineyard views
Exceptional
(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
AU$9,816
for 7 nights, 1 home
AU$1,402 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
3 acres of beautiful land
.
Outdoor dining
Private kitchen
Exceptional
(82 reviews)

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

Hampton Bays

6% off
AU$11,575
for 7 nights, 1 home
AU$1,654 per night
includes taxes & fees
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Pool
Living area
Interior
Exceptional
(11 reviews)

Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house

Sag Harbor

8% off
AU$14,562
for 7 nights, 1 cottage
AU$2,080 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Couches on covered porch and outdoor dining table for 8
Featured as one of most beautiful poolsides
Living area on 1st floor with wood burning fireplace
Kitchen walks out to covered porch across length of entire back
Exceptional
(7 reviews)

IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES

Southampton

8% off
AU$25,890
for 7 nights, 1 home
AU$3,699 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
living room
Dining
Pool
kitchen
Exceptional
(60 reviews)

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

Southampton

8% off
AU$19,722
for 7 nights, 1 home
AU$2,817 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Stairs to the upstairs living room, kitchen and dining room
Pool
Terrace/patio
Living room
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
AU$11,391
for 7 nights, 1 home
AU$1,627 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Dining
Dining
Exterior
Room
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
AU$30,476
for 7 nights, 1 home
AU$4,354 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Private kitchen
Terrace/patio
Interior
Dining
Exceptional
(20 reviews)

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

Greenport

8% off
AU$6,630
for 7 nights, 1 home
AU$947 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
The kitchen is all glass with a spectacular view of the pool and creek
A view of the house and pool from the creek, looking south
The front of the house
The front porch
Exceptional
(21 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
AU$6,166
for 7 nights, 1 home
AU$881 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Private kitchen
Dining
Living area
Room
Exceptional
(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off
AU$6,938
for 7 nights, 1 cottage
AU$991 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Open entry foyer with wall of windowed doors to Zen Garden
Thermador chefs kitchen with expansive island open to dining room & family room
Dining room seating 12 leading to chef's kitchen and doors leading to pool
View from entry foyer into double height living room, skylights, leading to pool
Exceptional
(6 reviews)

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

Wainscott

8% off
AU$23,177
for 7 nights, 1 home
AU$3,311 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Property grounds
Private kitchen
Room
Dining
Exceptional
(14 reviews)

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

Southold

8% off
AU$6,410
for 7 nights, 1 home
AU$916 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Room
Kitchen
Exterior
Living Room
Exceptional
(6 reviews)

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

New Suffolk

8% off
AU$4,830
for 7 nights, 1 home
AU$690 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Kitchen Fireplace Eat In Kitchen & in the next photo includes new kitchen table
Crushpad of Charming Boutique vineyard nearby- Rosehill
Living area
Exceptional
(30 reviews)

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

Laurel

26% off
AU$3,518
for 7 nights, 1 home
AU$503 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk

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    Enjoy full kitchens, laundry, pools, gardens and more

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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)
  • Havens Beach (6.6 mi / 10.7 km)
  • Georgica Beach (7 mi / 11.3 km)
  • Meschutt Beach (8.1 mi / 13.1 km)
  • East Hampton Main Beach (8.2 mi / 13.2 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 best area to stay in Water Mill when booking a holiday rental?
When considering a holiday rental in Water Mill, New York, the area offers a charming blend of serene countryside and coastal beauty. One of the most appealing neighbourhoods is the area near the picturesque Water Mill Pond, where you can find a selection of delightful properties that boast stunning views and a tranquil atmosphere. This part of Water Mill is renowned for its lush landscapes and proximity to the beach, making it great for those looking to relax and enjoy the outdoors.In addition to the scenic surroundings, staying near the pond allows easy access to top attractions like the Water Mill Museum, which showcases the rich history of the area and offers insights into the local culture. Just a short drive away, you can explore the beautiful beaches of the Hamptons, providing ample opportunities for swimming, sunbathing, and watersports.Another lovely area to consider is close to the local shops and eateries, where you can experience the vibrant community spirit and enjoy a delightful meal after a day of exploration.
Where are the best areas for renting a beach house in Water Mill?
For renting a beach house in Water Mill, consider the picturesque area surrounding the coastline near Mecox Bay. This charming neighbourhood is known for its serene beaches and beautiful waterfront properties. Many of the beach houses in this region offer amenities such as expansive outdoor decks, private pools, and direct beach access, great for families or groups seeking a relaxing getaway.Additionally, the nearby Water Mill Beach provides a family-friendly atmosphere with soft sands and calm waters, making it an excellent spot for swimming and sunbathing. Properties in this area often feature spacious living areas, modern kitchens, and outdoor grilling facilities, ideal for entertaining.Moreover, the proximity to local attractions such as the Water Mill Museum and various upscale restaurants enhances the experience for visitors. Many rentals also come with bicycles or beach gear, allowing guests to explore the scenic surroundings at their leisure.
Are there any family house rentals in Water Mill?
In Water Mill, New York, there are numerous family-friendly house rentals available, with around 51 options to choose from. This charming area is known for its picturesque landscapes and proximity to beautiful beaches, making it an excellent choice for families. Many of these properties boast spacious living areas, fully equipped kitchens for family meals, and outdoor spaces great for children to play.Visitors will find amenities such as private pools, game rooms, and cozy lounges, ideal for relaxation after a day spent exploring the local attractions. The nearby Hamptons provide additional entertainment options, including upscale dining, shopping, and cultural experiences. Families can also enjoy the scenic beauty of the surrounding parks and beaches, ensuring a memorable stay in this delightful locale.
Can I rent a holiday home with a pool or hot tub in Water Mill?
In Water Mill, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 66 options to choose from. This picturesque area in the Hamptons offers a serene environment, ideal for relaxation and enjoyment. Many properties boast private swimming pools, inviting hot tubs, and spacious outdoor areas great for entertaining or unwinding after a day at the beach.Travellers can expect amenities such as fully equipped kitchens, air conditioning, and well-furnished living spaces. Some rentals may also include additional features like outdoor dining areas, fire pits, and lush gardens, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Water Mill?
In Water Mill, there are numerous pet-friendly house rentals available, with around 48 options to choose from. This charming area, located in the Hamptons, offers a mix of luxurious holiday homes and cosy retreats, many of which come equipped with amenities such as private pools, spacious gardens, and modern kitchens.The neighbourhood is known for its beautiful landscapes, and visitors can enjoy the nearby beaches, which are superb for walks with pets. Additionally, the proximity to local parks and nature reserves provides ample opportunities for outdoor activities. Water Mill's community also features pet-friendly cafes and shops, ensuring that both travellers and their furry companions have an enjoyable stay.
Are there any remote work holiday rentals in Water Mill?
In Water Mill, New York, there are plenty of remote work holiday rentals available, with around 284 properties suiting those looking to blend work and leisure. This picturesque area, known for its charming rural landscape and proximity to beautiful beaches, offers a variety of accommodations that are well-suited for remote working. Travellers can expect amenities such as reliable Wi-Fi, dedicated workspaces, and comfortable desk chairs in many of the rentals. Some properties may also include additional features like printers and high-speed internet access, ensuring a productive environment.Situated close to the stunning Hamptons, Water Mill provides easy access to local attractions, including pristine beaches and delightful restaurants. The serene surroundings create an ideal atmosphere for balancing work commitments with relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Water Mill?
In Water Mill, popular holiday rentals often feature a range of desirable amenities that cater to comfort and leisure. Most properties include fully equipped kitchens, allowing guests to prepare their own meals. Many rentals also boast private pools, providing a superb spot for relaxation during warmer months. Additionally, outdoor areas such as decks or patios are common, offering spaces for al fresco dining or simply enjoying the serene surroundings. For those who appreciate a cosy atmosphere, fireplaces are frequently included, enhancing the warmth of the living spaces. Onsite parking is another convenient amenity that many rentals provide, ensuring easy access for guests arriving by car.
When is the best time to visit Water Mill for a holiday rental?
July is the most popular time to visit Water Mill, where visitors flock to enjoy the picturesque coastal charm of this Hamptons gem. The peak season runs from June to August, attracting those eager to indulge in outdoor activities, from beach days to exploring the local art scene. The warm summer climate, with temperatures typically ranging from 20 to 30 degrees Celsius, provides a great backdrop for sun-soaked adventures and leisurely strolls along the waterfront.During this vibrant time, you can immerse yourself in the lively option, with an abundance of events and activities, including farmers' markets and music festivals that celebrate the spirit of the Hamptons. If you're looking for the best experiences, July stands out as the month when Water Mill truly comes alive, filled with fellow holidaymakers enjoying everything the area has to offer.For those considering a more budget-friendly option, December presents a quieter yet charming time to visit. It's cooler, this month offers a unique opportunity to enjoy the serene beauty of Water Mill, where you can take peaceful walks along the beach and appreciate the local holiday festivities without the hustle and bustle of summer crowds.
What are the top attractions in Water Mill?
In Water Mill, visitors can enjoy a serene blend of natural beauty and cultural attractions. The area is known for its picturesque landscapes, including stunning beaches and scenic farmlands. One of the highlights is the nearby Mecox Bay, which offers opportunities for kayaking and paddleboarding, great for those looking to immerse themselves in the tranquil surroundings.Art enthusiasts can explore the Parrish Art Museum, located just a short drive away in Southampton, showcasing a diverse collection of American art, particularly from the local region. The charming countryside features several vineyards, where visitors can indulge in wine tastings and tours, contributing to the area's appeal for those seeking a leisurely getaway.
Are all fees included in the Water Mill holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Water Mill holiday homes with parking?
Stayz offers a wide selection of holiday homes in Water Mill with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Water Mill holiday homes?
You can find great discounts on holiday homes in Water Mill on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Water Mill holiday home booking on Stayz?
To find Water Mill holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Water Mill?
A long-stay holiday home in Water Mill is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Water Mill holiday home?
Book your Water Mill holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Water Mill?
Prices for holiday homes in Water Mill vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Water Mill to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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