Vacation rentals in Northwest Harbor

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, 467 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

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.

4.94 out of 5 average rating, 313 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.

4.99 out of 5 average rating, 106 reviews

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

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.

Apartment in The Hamptons

A spacious sleeping area is featured with a large bed adorned with a colorful blanket. Two bedside lamps are placed on sleek nightstands, and a full-length mirror leans against the wall. An entertainment unit with a TV is positioned opposite the bed, complemented by light wood flooring.

4.96 out of 5 average rating, 26 reviews

Newly renovated, private studio.

Enjoy a tranquil, private retreat in a natural, rustic setting < 1 mile from 2 bay beaches, @ 5 miles from East Hampton, and @ 4 miles from Sag Harbor. This studio has a separate entrance with a deck and garden, an attached bathroom, a cooking alcove, a sitting area, a bar/work station, individual climate control and a Roku tv. The owners live on premises but often travel for work. While everything in this studio is brand new, the setting is fairly rustic—not your typical Hamptons mansion.

A swimming pool with clear blue water is surrounded by a spacious deck. Lounge chairs with striped cushions are arranged for relaxation. Colorful umbrellas provide shade over outdoor sofas, and lush greenery in the background enhances the serene environment.

4.93 out of 5 average rating, 159 reviews

Large heated pool, games room, near private beach

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

Apartment in The Hamptons

A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.

4.98 out of 5 average rating, 194 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Guesthouse in The Hamptons

A cozy bedroom features a queen bed with a light blue quilt and a green loveseat nearby. Natural light enters through sliding glass doors, revealing a serene outdoor space. A decorative plant and framed artwork add a touch of interest to the room.

4.82 out of 5 average rating, 336 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house with use of amenities (shared with our family of 4). The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, micrwave, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for guests. 2 Adult guests ONLY (no children) due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets.

The exterior of the home features a modern facade with natural wood siding and a green lawn surrounding a heated pool. Two umbrellas provide shade for patio seating, while large windows allow for ample natural light. Trees frame the backdrop for a serene atmosphere.

4.97 out of 5 average rating, 35 reviews

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Elegantly designed 7 Bedroom / 7 Bath home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches and the vibrant Easthampton Village. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Kindly 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 are smoke-free.

Superhost

A modern black-clad home is visible with large windows reflecting soft light. Lounge chairs line the pool area, accompanied by umbrellas providing shade. A playful inflatable is positioned in the sparkling aqua pool, framed by lush greenery creating a serene outdoor environment.

Cottage in The Hamptons

4.76 out of 5 average rating, 105 reviews

Spacious East Hampton Getaway with Pool

This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

4.98 out of 5 average rating, 47 reviews

A spacious living area is highlighted by a stone fireplace, flanked by large windows that provide ample natural light. Wooden beams run across the ceiling, complementing the neutral-toned furnishings, including a cozy sofa. A dining table is visible in the background, surrounded by greenery.

Cottage in The Hamptons

Chic cottage on lush, secluded acre by the beach.

Charming cottage with spacious lawn surrounded by lush vegetation and protected land. 5-minute walk to a secluded and serene Northwest Harbor beach. An approximately 10-minute drive from both East Hampton and Sag Harbor restaurants and stores. Chic and modern rooms with brand-new, high-end bathrooms. Perfect rental for those who want a mix of quiet time and quick access to everything else. Relax and unwind at this unique and tranquil getaway.

Guest suite in The Hamptons

4.97 out of 5 average rating, 173 reviews

B our guest! King bed 2 bths Fireplace convenient

Beautiful, bright, spacious King suite w fireplace, two bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book/movie! The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

An outdoor patio features multiple wooden lounge chairs arranged around a central fire pit. A gunite pool with clear water reflects the surrounding greenery. The main house, visible in the background, showcases a classic design with white siding and large windows.

4.86 out of 5 average rating, 273 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

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Popular amenities for Northwest Harbor vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Northwest Harbor

A sleek modern farmhouse exterior is displayed, featuring a heated saltwater pool at the forefront. Comfortable seating arrangements surround the pool area, and expansive glass windows illuminate the interior. Lush greenery borders the property, contributing to a serene outdoor environment.

5 out of 5 average rating, 7 reviews

Hamptons Film Festival sanctuary

A living room is featured with a stone fireplace as the focal point, surrounded by wooden cabinetry. Large windows invite natural light, and a mix of seating options includes a gray sofa and two blue chairs. A coffee table sits at the center, adorned with a decorative bowl.

4.98 out of 5 average rating, 215 reviews

Sag Harbor home away from home

Guesthouse in The Hamptons

A serene view of a spacious barn with a deck illuminated by the golden light of sunset. Surrounded by lush foliage, the barn features large windows and a welcoming porch, providing a glimpse of modern yet comfortable architecture.

4.9 out of 5 average rating, 213 reviews

Beautiful Airy Barn in Springs

Guesthouse in The Hamptons

The exterior of the cottage is presented, showcasing a two-story wooden structure with dark wooden siding. Two windows are visible on the upper floor, framed by natural greenery. A small porch area, with stone accents, invites guests to step inside.

5 out of 5 average rating, 6 reviews

Peaceful cottage

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.

4.83 out of 5 average rating, 36 reviews

East Hampton Secluded Escape with Gunite Pool

A bright living space features a classic sofa, two armchairs, and decorative lighting. A stone fireplace adds a cozy element, while a large window invites natural light. Indoor plants provide greenery, and a kitchen area with modern appliances is visible in the background.

4.85 out of 5 average rating, 126 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

The heated saltwater pool is surrounded by lush greenery, creating a serene atmosphere. Colorful pool floats in the shape of a flamingo and palm leaves rest on the surface. A hammock is visible nearby, inviting relaxation under the dappled sunlight.

4.97 out of 5 average rating, 32 reviews

Chic & Spacious Designer Home, Heated Pool/Spa