Holiday houses in Northwest Harbor

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

4.95 out of 5 average rating, 266 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

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A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

4.95 out of 5 average rating, 523 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

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A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

4.98 out of 5 average rating, 147 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway. (No AI used in these photos!)

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4.93 out of 5 average rating, 136 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

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Luxe

An aerial view of the Mid Century Modern home is showcased, surrounded by lush greenery. The spacious yard features a heated pool, deck chairs, and a large checkered game board. A shaded seating area is positioned nearby, offering a perfect gathering spot amidst the natural landscape.

Villa in East Hampton

4.99 out of 5 average rating, 69 reviews

SERENITY AT SHOREWOOD Pool is Open April 1 - November 1. Must be 25+ to book. Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

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4.87 out of 5 average rating, 47 reviews

Private East Hampton Estate

Relax in the serenity and privacy of this East Hampton estate located on a private drive, surrounded by beautiful homes on five acres lots creating extreme quiet and privacy. The home features four bedrooms, three and 1/2 baths, heated gunite pool, beautiful landscaping, fire pit, blue stone decking, outdoor dining/entertaining areas, chef's kitchen, TV den, formal living room, family/recreation room and a master suite with office. Just minutes to East Hampton village & beaches.

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4.94 out of 5 average rating, 155 reviews

A comfortable living room area is presented, featuring a light-colored sectional sofa arranged around a wooden coffee table. Natural light enters through a large window, illuminating a piece of artwork on the wall and adding a cozy touch to the space.

Apartment in Sag Harbor

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

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An in-ground salt-water pool is surrounded by natural stone, set amidst lush greenery. Sun loungers are positioned alongside the pool, and a shaded seating area is visible to the right. A wooden structure stands in the background, blending with the tranquil landscape.

4.9 out of 5 average rating, 67 reviews

East Hampton Secluded Escape with Gunite Pool

Elegantly furnished 4 bedroom house on lushly landscaped grounds, fewer than 5 minutes from the heart of East Hampton Village. This home is ideal for outside living, featuring a gunite, in-ground salt-water pool and stone patio. The interior is bright and spacious, accented by minimalist yet warm furnishings. Common living areas include a large family room with TV, large dining room with gas fireplace, and a large eat in kitchen. Rental registry HMT23-10468

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A modern living area is highlighted by a spacious sectional sofa and large windows providing natural light. A dining space with a round chandelier and a kitchen with new appliances are visible. The room features hardwood floors and a decorative fireplace, enhancing the open layout.

4.94 out of 5 average rating, 121 reviews

Marvelous 4 Bed East Hampton home w Heated Pool

Beautiful, designer home with new appliances located just a few short minutes to ocean beaches, Wolffer Vineyard, East hampton /Sag Harbor villages. The home has mature landscaping and pristine. Every attention to detail has been met. Please read my disclosures & house manual before you request in order to be on the same page. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

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4.85 out of 5 average rating, 53 reviews

Historic Home + Private Waterfront Access

A rare piece of East Hampton architectural history. Designed in 1958 by Kaneji Domoto, a student of Frank Lloyd Wright, this mid-century home celebrates indoor-outdoor living with walls of glass, abundant natural light, and panoramic views of Three Mile Harbor. Set among mature trees with a private staircase down to the water, the home offers a truly unique Hamptons experience - from sunrise coffees to unforgettable sunsets.

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A spacious backyard features a large pool surrounded by a wooden deck. Two lounge chairs are positioned beside the pool, and an umbrella provides shade nearby. Lush greenery lines the property, creating a serene and private environment for relaxation and recreation.

4.94 out of 5 average rating, 53 reviews

Sunny, walk to beach, large pool

Walk to the beach from the quiet of the woods! Sunny, contemporary family-friendly house with large pool in the hidden gem of the Northwest Woods section of East Hampton. Walk to Sammy's Beach on the Gardner's Bay, or make a quick drive to the ocean, come home to grill on the large deck and swim in the large heated pool. 40 acres of nature preserve behind you for quiet + unspoiled scenery!

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4.95 out of 5 average rating, 324 reviews

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

Home in Sag Harbor

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

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Popular amenities for Northwest Harbor holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Northwest Harbor

A private swimming pool reflects clear blue skies, surrounded by lounge chairs and umbrellas. Lush greenery frames the scene, while a wooden deck leads to the main house, which features a modern architectural design. A swing set adds an element of leisure to the serene outdoor space.

4.94 out of 5 average rating, 51 reviews

¤¤¤ Wonderful retreat on 4 acres with pool ¤¤¤

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The charming exterior of a cedar shingle house is framed by lush greenery. A welcoming entryway features a blue front door, complemented by symmetrical windows on either side. The landscaped front yard includes low shrubs and a gravel pathway leading to the entrance.

4.79 out of 5 average rating, 72 reviews

Beautiful E. Hampton Home w/ Brand New heated pool

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4.95 out of 5 average rating, 42 reviews

A spacious living room is featured, characterized by whitewashed beams and large windows allowing natural light. A soft, neutral sofa is positioned in front of a gold-accented coffee table. Decorative plants and a subtle area rug add warmth to the space, enhancing the inviting atmosphere.

Cottage in Bridgehampton

Hamptons Designer Cottage w Pool by Wölffer Estate

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An aerial view of a backyard features a spacious wood deck surrounding a gunite pool. Comfortable lounge chairs are positioned near the pool, alongside a shaded area with an umbrella. The natural greenery provides a serene backdrop to the outdoor dining area.

5.0 out of 5 average rating, 57 reviews

Secluded Luxury: New Gunite Pool, Walk to Bay

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A spacious dining area features a large wooden table surrounded by white chairs. Natural light streams through multiple windows, highlighting the warm tones of the decor. Stylish woven pendant lights hang from the ceiling, creating an inviting atmosphere for gatherings.

4.96 out of 5 average rating, 24 reviews

Tasteful Hampton 4 Bedroom w Heated Pool EH / Sag

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5.0 out of 5 average rating, 24 reviews

Chic house NW Woods. Massive 50 ft heated pool.

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5.0 out of 5 average rating, 18 reviews

Cottage in Sag Harbor

Hamptons Waterfront Getaway – Stylish & Serene

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