Vacation rentals in Water Mill

5.0 out of 5 average rating, 52 reviews

Charming House In The Village

Keep it simple at this peaceful and centrally-located place in the Heart of Southampton Village Escape to this delightful house nestled in the heart of Southampton Village, offering a perfect blend of charm, comfort, and convenience. Situated just moments away from the beach, and walking distance to restaurants and entertainment. 🏠 Entire First Floor (Private) 🛏️ Bedrooms: 2 🛁 Bathrooms: 1 🌳 Outdoor Space: Private Garden  🔥 Fire Pit and BBQ 🚘 Two Parking Spaces 👨‍🍳 Fully Stocked Kitchen

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.

4.93 out of 5 average rating, 139 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.

4.86 out of 5 average rating, 80 reviews

Home in Shinnecock Hills

Chic Southampton Home. Mins to Village and Beach!

Welcome to your perfect Hamptons getaway! This sun-filled, architecturally unique home is ideal for a summer retreat or a cozy weekend escape. Offering modern furnishings, and an open floor plan, this space is perfect for small groups. Whether you're enjoying the crisp evenings of early spring, sun-drenched summer days, or the vibrant fall season, this home is a serene escape year-round. Cozy up by the fire, relax on the sun-soaked balconies, or unwind in the beautifully renovated pool house.

5.0 out of 5 average rating, 20 reviews

Cottage in Sag Harbor

Hamptons Waterfront Getaway – Stylish & Serene

Waterfront Luxury Retreat in Sag Harbor. As featured in Vogue, Mansion Global, and Homeworthy. This serene designer home offers direct bay access for kayaking and paddle boarding, plus a private path to Clam Island for peaceful walks and beach picnics. Enjoy a gourmet kitchen with Viking and Sub-Zero appliances, spa-like en-suite baths, and plush bedding. Minutes to bay beaches and Sag Harbor village—your private escape awaits. Ideal for romantic getaways, relaxing weeks, or a summer reset.

4.98 out of 5 average rating, 80 reviews

A spacious lawn is bordered by tall trees, providing a natural frame for the cottage. The vibrant green grass leads to a serene waterfront, where the lake reflects the sunlight. The peaceful setting invites relaxation and outdoor activities.

Cottage in Water Mill

Head of Pond House - Waterfront Cottage

Welcome to the charming, waterfront Cottage at Head of Pond House! Enjoy a peaceful retreat with beautiful lake access year-round and pool access from Memorial Day to October. The cottage features two comfortable king beds, including one in a cozy loft area, a full bath, WiFi, a projector for movie nights, and a fully stocked kitchen. Whether you’re looking for a relaxing escape or a comfortable base to explore the Hamptons, our waterfront cottage is the perfect spot for your getaway.

4.96 out of 5 average rating, 25 reviews

Brand New Sun Filled Home

OUR HOUSE A beautiful newly renovated Southampton two story home with spectacular light, offering the best of indoor-outdoor living. A large deck off of the kitchen with small porches off of two primary suites and a small sitting area off the first floor junior suite. On almost one acre of land, there is plenty of peaceful space. Very central - two miles from the beach and town. Two car garage with built in electric vehicle charger. Gas fireplace. All appliances are brand new.

The airy living space features white shiplap walls and a high ceiling, accented by natural light from multiple windows. A gray sofa is paired with a glass coffee table, while a decorative fireplace adds charm. A ceiling fan provides airflow, enhancing the inviting atmosphere.

4.89 out of 5 average rating, 312 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

5.0 out of 5 average rating, 20 reviews

Luxury Southampton Home/outdoor Sauna/hottub

This stunning 5-bedroom, 2-story Traditional home sits on just under an acre in Southampton, NY. It features a living room with a vaulted ceiling and fireplace, a gourmet kitchen with a dining area, a sunroom, and five bathrooms. The property includes a 2-car garage and a finished basement that offers a billiard room, media room, kitchenette, and bath. For summer gatherings, enjoy the 20' by 40' heated pool, expansive mahogany decking, and beautifully designed landscaping.

A modern two-story home stands illuminated at dusk, showcasing a welcoming porch with wooden steps. The facade features a combination of white metal and black trim. Lush landscaping with lighted pathways guides visitors toward the entrance, enhancing the exterior's contemporary appeal.

4.98 out of 5 average rating, 41 reviews

Hamptons Modern Retreat NEW CONS

ARCH&Co® presents: ♥♥♥Hampton's Modern Barn Retreat NEW CONSTRUCTION! 6 bedroom suites, 6 bathrooms- pool with deck, theater, an amazing backyard with indoor / outdoor living. Set on a cul-de-sac. Sleeps 12!! Quick facts: -Heart of Water Mill / Southampton! 10 Minutes from the beach and village! -Custom designed home by professional Hospitality company- ARCH&Co® - King size bedrooms each with own en-suite bathrooms (6 bathrooms total). No Sharing Bathrooms Here!!

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.

4.92 out of 5 average rating, 131 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. We are a pet friendly home so if allergic please be aware. 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!

The outdoor area features a large, heated saltwater pool surrounded by lounge chairs. Lush hydrangeas bloom nearby, adding color to the landscape. A two-story home stands in the background, accented by patio umbrellas and trees, contributing to a relaxed garden atmosphere.

4.93 out of 5 average rating, 59 reviews

Awesome Watermill 5 Bedroom with a heated pool

Perfectly located moments to Bridgehampton, Southampton's Main Street and Ocean beaches, this charming 5 bedroom and 4.5 bath home is situated on a very private street. The newly restored and planted garden is surrounded by 12ft mature privet hedges and punctuated by a heated pool. The home is sundrenched with many of the rooms having captivating views out to the immense garden.

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.

4.94 out of 5 average rating, 167 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 –

Popular amenities for Water Mill vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Water Mill

4.95 out of 5 average rating, 62 reviews

A large outdoor pool is surrounded by lounge chairs and umbrellas, inviting relaxation. Well-maintained gardens and trees frame the area, with a spacious deck along one side. The bright blue sky enhances the tranquil atmosphere of this inviting outdoor retreat.

Home in Shinnecock Hills

Spectacular Southampton Retreat!

A large swimming pool is surrounded by lush greenery and carefully arranged flower beds. A charming barn with a cross-patterned door is visible in the background, alongside a wooden bench set among mature trees, creating a serene outdoor environment.

4.81 out of 5 average rating, 42 reviews

Charming Water Mill Get Away

4.94 out of 5 average rating, 16 reviews

Cottage in Southampton

Steps to Train, Dining & Coopers Beach SH village

4.98 out of 5 average rating, 97 reviews

Southampton Estate w Heated Pool

An open-plan living area features a spacious dining table surrounded by black chairs. Natural light floods in through several windows and skylights, illuminating the modern kitchen equipped with sleek cabinets and stainless-steel appliances.

4.97 out of 5 average rating, 61 reviews

Renovated Southampton Home+Pool

5.0 out of 5 average rating, 4 reviews

Home in North Fork

Bungalow by the Bay

Guesthouse in Southampton

A serene outdoor space showcases a heated saltwater pool framed by neatly trimmed hedges. Comfortable lounge chairs are arranged beside the water, while a large umbrella provides shade. A two-story house is visible in the background, surrounded by greenery.

3 Bedroom Guest House in Southampton

4.96 out of 5 average rating, 23 reviews