Family-friendly holiday rentals in Bridgehampton

A charming view is displayed through a large window, overlooking a green lawn that leads to a serene waterway. A decorative piece resembling a swan rests on a small table, casting a soft shadow as sunlight streams in.

4.91 out of 5 average rating, 175 reviews

Whaling Captain Pierson's Cottage

Whaling Captain Pierson's Cottage is at a waterfront property. A unique environmental experience, nestled in nature but only a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets and a private low-tide beach. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

4.88 out of 5 average rating, 130 reviews

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

Home in Sag Harbor

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

4.96 out of 5 average rating, 103 reviews

A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.

Flat in Southampton

Swimming pool w/Hot tub Fire Pit Coffee Bar

Relax in this cozy loft filled with amenities that will create lasting memories. Recently renovated so fresh and clean. Located on a wooded lot. Large fenced in landscaped yard with hammocks and firepit. Heated pool seasonal. We are just minutes from the beach. Spend time in our 6 person jacuzzi. 10 min to Southampton village. 15 min to Sag Harbor. Centrally located. Fresh farm (home of Tate’s Cookies) around the corner with fresh meats and produce. A tasty restaurant near by and a deli too.

Guest house in Southampton

A charming outdoor area features a black cottage in the background, with large glass doors reflecting the surroundings. The deck is adorned with potted red geraniums and wooden seating. A hot tub is positioned adjacent to the cottage, emphasizing a tranquil retreat atmosphere.

4.97 out of 5 average rating, 117 reviews

5 Star Rated Private Cottage Southampton/Sag Hrbr

The Honeycomb Cottage is a little retreat located on a lush acre of evergreens in Southampton rated 5 Star by every guest that has stayed. One block to Peconic Bay Beach - perfect for a day in the sun. A cozy space with TV, WiFi and Sun Deck. Luxury soaps provided, amazing shower and crisp white linens. Exclusive use of the Hot Tub for Cottage guests. Easy parking and located 15 minutes drive to Sag Harbor or Southampton Village. Koi pond with waterfall will sooth the mind and spirit.

4.99 out of 5 average rating, 116 reviews

A well-maintained outdoor space features a large swimming pool surrounded by a wooden deck. Lounge chairs are placed around the pool, with red umbrellas providing shade. Adjacently, a patio area includes a dining table. Lush greenery frames the area, contributing to a serene ambiance.

Guest house in Springs

The Quail’s Nest

A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

Superhost

An airy living space features exposed wooden beams and large windows allowing natural light to fill the room. A modern yellow sofa and a dining table with elegant chairs create a welcoming atmosphere. Decorative elements include a gold-framed artwork and bronze accent tables on a soft area rug.

Home in Water Mill

4.88 out of 5 average rating, 105 reviews

Designer's Own, w Pool, 5 min. to Ocean & Village

Our 4BR airy home in a prime Hamptons location--Water Mill South--offers comfort, luxury, and tranquility, all while being just 5 min. away from ocean beaches, restaurants in Bridgehampton Village, and the area's best fields and farm stands. Impeccably renovated, comfortable, family-oriented traditional shingle house is in a quiet, established neighborhood perfect for walks or bike rides. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking

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.

4.99 out of 5 average rating, 228 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!

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.

4.94 out of 5 average rating, 155 reviews

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 .

4.99 out of 5 average rating, 135 reviews

A sunset scene is captured over a sandy landscape, where vibrant shades of orange and pink fill the sky. Silhouettes of beach fencing and grassy dunes are visible in the foreground, complemented by a wooden structure to the right.

Home in Hampton Bays

Charming House close to Ocean Beaches

Entire House! Large fenced in yard, great for pets. Two bedrooms, one song ride away from Ponquogue Beach. Have the beach to yourself for walks and exercise! Perfect place to get away and Unwind. The house is located on a quiet residential street close to the hamlet of Hampton Bays. Enjoy the patio and fire pit (use non-windy days) on 1/4 acre property. Still plenty to do here, we are 20 minutes from Wine Country and Tanger Outlets.

Superhost

A compact living area features a blue sofa adorned with patterned pillows and a geometric area rug. A dining table with two wooden chairs is positioned near a mirror reflecting natural light from the window. Potted plants add a touch of greenery to the space.

Cottage in Bridgehampton

4.84 out of 5 average rating, 100 reviews

Cottage 3 minute walk Bridgehampton town

Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. Depending check in/out flexible. 5min. drive or less 10 min. Bike to Hampton classic. Fenced backyard. Near Hampton jitney, train. Walk to town,fitness, bike to the ocean rd. beach. Same road of nature reserve, kids museum, farmers market. 5 min. drive to commons. Grill,Bikes,beach chairs+toys,Yoga mats, SUP Boards. $50+pet fee- number, size,duration of stay.

A bright living area features two windows, allowing natural light to fill the space. A white sofa and an accent chair are positioned around a small coffee table. Artwork adorns the walls, complementing the light color palette. A dining table with two chairs is visible in the corner.

4.9 out of 5 average rating, 181 reviews

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 10 minute walk to historic Sag Harbor Village Main Street. Five minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea kettle. Strictly 2 person max. Not suitable for infants/children No pets - owner is allergic.