Vacation rentals in Water Mill

5.0 out of 5 average rating, 18 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.

4.95 out of 5 average rating, 21 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.

5.0 out of 5 average rating, 19 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.

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, 130 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!

4.93 out of 5 average rating, 15 reviews

Cottage in Southampton

Steps to Train, Dining & Coopers Beach SH village

SOUTHAMPTON HOUSE NEW YORK charming cottage escape with a separate guest house, perfect for 7 guests. Relax in our private courtyard, complete with an outdoor kitchen with green egg, and fireplace for cozy nights under the stars. Just steps from the LIRR and walkable to downtown’s boutiques, restaurants, and attractions, our location is unbeatable. We’re just 2 miles from Coopers Beach.

4.91 out of 5 average rating, 11 reviews

Southampton Village Escape

Welcome to 86 Hildreth St, a 3BR, 3.5BA gem steps from Main St. Built in 1930 and thoughtfully updated with central AC and bright, sun-filled interiors, it blends charm and comfort. The yard features a gunite pool and bluestone patio. Bike to Coopers Beach, grab lunch at Citarella, hit SLT, and make it to Sant Ambroeus for dinner. It’s walkable village life with a great Hamptons vibe.

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, 166 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 –

4.9 out of 5 average rating, 128 reviews

Apartment in Southampton

Oasis Hampton getaway

Located in the heart of southampton. 3miles away from main shopping areas.Room is newly remodeled and furnished . All upscale Ammenities. Electric toilet ,free WiFi, free Netflix , use of pool and bbq grill, fire pit, living room with 52”flat screen tv, kitchenette and dining area and driveway parking .

4.92 out of 5 average rating, 79 reviews

Scandinavian Cottage

Welcome to our cozy Scandinavian cottage, where modern design meets rustic charm. Nestled in the heart of a picturesque forest, our cottage offers the perfect retreat for those seeking a peaceful and relaxing getaway while being only 5 minute drive from Main Street and Southampton Beaches.

4.97 out of 5 average rating, 114 reviews

A cozy living area features a grey sofa adorned with decorative cushions, along with a white accent chair. Natural light floods in from two large windows, casting a warm glow on the wooden floor. An American flag decorates the wall, adding character to the space.

Apartment in Southampton

Stunning Garage Apartment!

A beautiful studio apartment with a full bathroom, a newly installed kitchenette, queen size bed and a separate living room with a 55" TV and sofa seating group. The apt has its own separate entrance from the main house and is close to beach or bay.

Popular amenities for Water Mill vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Water Mill

A charming two-story home features a shingle exterior, large windows, and a spacious front porch. A well-manicured lawn and blooming flower beds surround the property, enhancing its natural beauty. Outdoor seating is arranged on the porch, providing an inviting space for relaxation.

4.97 out of 5 average rating, 74 reviews

Newly Renovated SH Village 5bd with pool

4.98 out of 5 average rating, 61 reviews

A bright and airy outdoor space features a long pool bordered by lounge chairs and greenery. The white house stands in the background, with large windows reflecting the blue sky. An umbrella provides shade beside the pool, promoting relaxation.

Home in Shinnecock Hills

Luxe Southampton Home w/Pool 5 Min To Town & Beach

4.71 out of 5 average rating, 85 reviews

Southampton Village, Oversized Pool, Walk to All

4.87 out of 5 average rating, 76 reviews

Home in Shinnecock Hills

Chic Southampton Home. Mins to Village and Beach!

A serene Gunite pool is surrounded by a spacious patio featuring several lounge chairs beneath large umbrellas. Lush greenery lines the perimeter, enhancing the outdoor space's tranquility. The smooth surface of the pool reflects the clear blue sky.

4.81 out of 5 average rating, 86 reviews

Charming Southampton Village Home

An aerial view showcases a modern house surrounded by greenery, featuring large glass windows and multiple outdoor decks. A heated pool is nestled below, flanked by lounge chairs and umbrellas, creating an inviting space for relaxation and enjoyment.

5.0 out of 5 average rating, 18 reviews

Modern Oasis in Southampton

4.95 out of 5 average rating, 59 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!