Holiday houses in North Haven

4.91 out of 5 average rating, 141 reviews

Home in Springs

Serene + private ~ 1 block to waterfront dining

Enjoy zen living at this serene, chic, Hamptons oasis! Ideally located 1 block to waterfront dining, 8 minutes to beaches + 9 minutes to Main St! Relax poolside w/ tons of greenery + nature views. Spark up the BBQ + firepit under the starry sky. Listen to the crickets + spot a deer on the property. Curl up to the wood burning fireplace, cook in your Chef's kitchen + stream on your 80' TV Enjoy coffee on the sea + dinner w the best sunsets just 1 block away. A perfect escape + place to unwind!

FamilyLocationOutdoor spaces

4.94 out of 5 average rating, 334 reviews

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 Bridgehampton

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 grounds are smoke-free.

LocationFamilyCheckout

4.93 out of 5 average rating, 134 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.

ValueLocationDecor

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.

FamilyLocationIndoor spaces

4.91 out of 5 average rating, 202 reviews

Barefoot Bliss | Quiet Family Retreat Heated Pool

Welcome to your Hamptons retreat. This bright single-level home sits in a quiet neighborhood just minutes from Main Street and the ocean. The private fenced yard overlooks a peaceful nature preserve and features a heated pool (June–Sept, heating available for a fee), hot tub, outdoor fireplace, and outdoor shower—perfect after a beach day. Family-friendly amenities include a sandbox, toys, crib, and highchair, with a separate safety fence surrounding the pool for added peace of mind.

FamilyValueKitchen

4.98 out of 5 average rating, 241 reviews

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.

Apartment in Sag Harbor

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!

FamilyValueQuiet

A cozy living area is highlighted by a chandelier, providing soft illumination. Two stylish chairs flank a round table, while a decorative sculpture and a vintage fireplace enhance the space. Large windows allow natural light to fill the room, offering views of the surrounding greenery.

4.9 out of 5 average rating, 117 reviews

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

ValueFamilyBathroom

Superhost

4.88 out of 5 average rating, 16 reviews

4 Bedroom Sag Harbor Home w/ Pool & Tennis Access

*Please read the full Description* Perfect getaway for families, friends, or groups looking for a centrally located space to enjoy all that Sag Harbor has to offer. -4 bedrooms -2 full bathrooms -Kitchen with adjacent dining area -Two living spaces -Airy sunroom -Backyard with outdoor seating -Easy access to Long Beach and Main Street (car ride, bike, walk) -Park, Bay access close by Inquire below: IG @ Tal.Adla.Hamptons

FamilyLocationQuiet

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.

4.95 out of 5 average rating, 323 reviews

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.

LocationFamilyAccuracy

A serene waterfront scene captures a vibrant sunset, showcasing a blend of orange, pink, and purple hues reflected on calm water. A wooden dock extends into the water, while silhouettes of people can be seen engaging at the water's edge.

4.92 out of 5 average rating, 12 reviews

Sag Harbor Village Waterfront Cottage

Relax with the whole family at this peaceful place to stay. This waterfront Sag Harbor cottage is on a quiet street but walking distance to downtown. It's filled with beach life charm and offers the best sunsets in town sitting on the screened in porch, or on the dock benches. Enjoy paddle boarding, the big outdoor shower, expansive yard and private beach.

LocationFamilyOutdoor spaces

Superhost

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

Apartment in Shelter Island Heights

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

LocationFamilyQuiet

4.9 out of 5 average rating, 271 reviews

Cottage in Shelter Island

A traditional New England-style house features a front porch supported by white columns. Two white chairs and a small table are arranged on the porch, complemented by a dark front door. Large windows allow natural light to fill the space, surrounded by green landscaped areas.

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

LocationValueSleep quality

4.97 out of 5 average rating, 129 reviews

Popular amenities for North Haven holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in North Haven

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

FamilyValueSleep quality

5.0 out of 5 average rating, 77 reviews

Cottage in Sag Harbor

Charming Cottage in Historic Sag Harbor

LocationValueSleep quality

Home in Shelter Island Heights

A spacious house is framed by lush landscaping, featuring a large pool in the foreground. Sun loungers and patio umbrellas are arranged around the pool, along with a pink float. The exterior showcases a combination of shingle siding and solar panels under a clear blue sky.

Beautiful beach home with pool & water views!

LocationFamilyBiking

4.95 out of 5 average rating, 79 reviews

4.95 out of 5 average rating, 22 reviews

The exterior of the house is visible, showcasing a charming facade with natural wood shingles. A well-maintained lawn surrounds the property. A driveway leads to a garage, while white chairs are positioned on the porch, inviting a relaxing outdoor experience.

Home in Southold

Country Beach Home!

FamilyLocationCheck-in

4.94 out of 5 average rating, 50 reviews

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.

Home in East Hampton

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

FamilyValueWi-Fi

5.0 out of 5 average rating, 71 reviews

A spacious living area is filled with soft natural light, featuring a curved sectional sofa and a modern coffee table. A stylish armchair and decorative items are present. The background reveals an elegant staircase leading to an upper level, enhancing the room's contemporary design.

Cottage in Sag Harbor

Luxury Gem At The Heart of Sag Harbor Village

ValueLocationIndoor spaces