Holiday rentals in Watermill

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Top-rated holiday rentals in Watermill

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Guest favourite
A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.
Apartment in North Fork
4.89 out of 5 average rating, 157 reviews

Waterfront Autumn Escape in Wine Country: 2BR

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on your private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Top guest favourite
The image showcases a spacious outdoor area featuring a heated gunite pool surrounded by manicured grass. Four loungers with umbrellas are positioned near the pool, while a cozy seating arrangement is visible on the patio. A charming cottage is seen in the background.
Cottage in The Hamptons
4.96 out of 5 average rating, 100 reviews

Modern Southampton Cottage | Heated Pool & Peloton

Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

Superhost
A serene pool area is surrounded by lush greenery and colorful hydrangea flowers. Lounge chairs offer relaxation under large umbrellas, while the inviting pool reflects the clear blue sky. A charming home stands in the background, adding to the peaceful setting.
Home in The Hamptons
4.92 out of 5 average rating, 118 reviews

Southampton Charmer, 5 bedrooms w pool - Location

This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Guest favourite
Home in The Hamptons
4.88 out of 5 average rating, 113 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Top guest favourite
An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.
Home in The Hamptons
4.94 out of 5 average rating, 318 reviews

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

Guest favourite
An open-concept living space features a dining area with a rectangular wooden table adorned with a decorative bowl. A spacious couch is positioned near a fireplace, with large windows allowing ample natural light. A stylish chandelier hangs above, complementing the high, pitched ceiling.
Villa in The Hamptons
4.99 out of 5 average rating, 111 reviews

East Hampton Village Fringe, Renovated with Pool

This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Top guest favourite
A cozy sleeping area is highlighted by a spacious bed with light blue bedding, positioned near a working fireplace. A television is placed on a wooden stand across from the bed. Soft lighting from bedside lamps creates a warm ambiance, complemented by a decorative artwork on the wall.
Guest suite in The Hamptons
4.9 out of 5 average rating, 379 reviews

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

Top guest favourite
A bright and airy living space features large windows allowing natural light to fill the room. Wooden dining chairs surround a rectangular table, while comfortable seating is arranged in a cozy arrangement. Indoor plants add a touch of greenery, enhancing the inviting atmosphere.
Home in The Hamptons
4.93 out of 5 average rating, 124 reviews

Classic Southampton Village Home w/ Pool

Newly renovated Southampton village home with great light, offering the best of indoor-outdoor living. A beautiful backyard with a pool surrounded by lush privet hedges for privacy. Perfectly situated in the heart of the village, one block from restaurants, shopping, and one mile from the ocean beaches. Perfect with space to spread out, play or work remotely! Ask about special rates for long-term summer rental!

Superhost
A bright living area features a white sofa adorned with patterned blue pillows, positioned beside a rustic wooden coffee table. Large glass doors open to reveal a glimmering pool and lush outdoor landscaping, enhanced by vibrant potted plants and a shaded seating area.
Home in The Hamptons
4.89 out of 5 average rating, 134 reviews

Serene 3 Bed 2.5 Bath House w/Heated Pool

Situated off a quiet lane on a half-acre, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 3 wonderful bedrooms 2 modern bathroom and a heated saltwater pool ( See Pool heat and Pool Closure Details ) with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Guest favourite
A well-maintained outdoor pool area is surrounded by a wooden deck and lush greenery. Lounge chairs are positioned along the pool, with a shaded area provided by a large tree. The clear blue water of the pool reflects the sunlight, inviting relaxation.
Home in The Hamptons
4.94 out of 5 average rating, 146 reviews

Astounding Watermill 5 Bedroom home with Pool

Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Guest favourite
A wide sandy beach stretches towards the horizon, where soft waves gently lap at the shore. Tall lifeguard stands are positioned along the beach, with a few distant figures walking. The sky features a gradient of muted colors as the sun sets, creating a serene atmosphere.
Flat in The Hamptons
4.95 out of 5 average rating, 224 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

Top guest favourite
The exterior of a two-story home is visible, featuring large glass windows that promote natural light. A spacious wooden deck hosts a dining area with a white umbrella. Lush green grass and trees surround the area, creating a serene outdoor setting.
Home in The Hamptons
4.91 out of 5 average rating, 116 reviews

Elegant Modern Artist's Residence

This simple and serene home is set against a farm preserve, exposed to beautiful light and views and biking distance to the beach. Very relaxing - a terrific, creative space for a couple or small group. A large vegetable garden is maintained on the property and is available for guests to harvest as they like. Fresh salad greens, herbs, vegetables for you to enjoy!

Popular amenities for Watermill holiday rentals

When is the best time to visit Watermill?

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Avg. price$1,297 SGD$1,258 SGD$1,255 SGD$1,174 SGD$1,210 SGD$1,556 SGD$1,847 SGD$2,124 SGD$1,315 SGD$1,250 SGD$1,275 SGD$1,258 SGD
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Frequently Asked Questions

  • Do house rentals in Water Mill have free parking?

    Absolutely! We offer over 210 house rentals with free parking in Water Mill. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Water Mill have a kitchen?

    Absolutely! We offer over 220 house rentals with a kitchen in Water Mill. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Water Mill?

    Experience the best of Water Mill with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly house rentals in Water Mill?

    Water Mill has more than 210 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there Water Mill house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 190 house rentals with pools in Water Mill, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there pet-friendly cottage rentals in Water Mill?

    Four-legged friends are welcome in Water Mill. Choose from more than 10 cottage rentals for guests traveling with pets.

  • Do cottage rentals in Water Mill have air conditioning?

    Absolutely! We offer over 10 cottage rentals with air conditioning in Water Mill. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Water Mill have wifi?

    Absolutely! We offer over 220 house rentals with wifi in Water Mill. Enjoy a tailored experience with all the comforts you desire.

  • Are there house rentals with a dedicated workspace in Water Mill?

    Yes! Work meets play with ease at over 140 house rentals in Water Mill featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in Water Mill?

    Enhance your stay in our House Rentals with the most popular amenities: over 220 homes with air conditioning, over 210 homes with free parking, over 220 homes with wifi, over 220 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Watermill

  • Total holiday rentals

    Explore 270 holiday rentals in Watermill

  • Nightly prices starting at

    Watermill holiday rentals start at $182 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,920 verified reviews to help you choose

  • Family-friendly holiday rentals

    240 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    230 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    260 of Watermill holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Watermill rentals

  • 4.8 Average rating

    Watermill stays are highly rated by guests – averaging 4.8 out of 5!

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