Holiday rentals in Bridgehampton

A two-story beach house features wooden shingle siding and large windows. A sparkling blue pool is positioned in the foreground, surrounded by a wooden deck. Comfortable lounge chairs are placed nearby, offering options for relaxation outdoors.

4.76 out of 5 average rating, 51 reviews

Cheerful 3 bedrm-4 beds-3 bath -beach home w pool

Heart of the Hamptons is situated this bright, beach house 5 min from the ocean, BH/Sag Harbor town, & Wolfer vineyards. 2 master suites w/ ensuite bathrooms and an additional guest room with adjacent bathroom that comfortably sleeps 6 -1 King, 1 queen, 2 twin. Open kitchen that adjoins the dining area and the double height living room w/ fireplace. Sparkling heated (add charge) pool (MD-mid Sept) and palatial lawns with room to roam. Keep it simple at this peaceful and centrally located getaway

4.99 out of 5 average rating, 214 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.

Flat in The Hamptons

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!

The exterior of the cottage is framed by lush greenery and mature trees, showcasing a charming facade with a combination of wood shingles and a welcoming entryway. Stone steps lead to the porch, while a manicured lawn enhances the inviting atmosphere.

4.98 out of 5 average rating, 43 reviews

Sag Harbor Chic Modern Cottage

Escape to this charming Sag Harbor cottage, featuring three inviting bedrooms, two full baths, a cozy living room, light and airy sunroom, and a sun-filled kitchen and dining area. Relax in the delightful sunroom or unwind in the beautifully landscaped private garden, complete with a bluestone patio and a picturesque pergola. Perfectly situated just minutes from pristine bay and ocean beaches, marinas, scenic nature preserves, farm stands, acclaimed restaurants, and boutique shopping.

A spacious backyard is showcased, featuring a large saltwater pool surrounded by six lounge chairs. Lush green grass is complemented by a flowerbed, while tall trees provide shade. The house, with a wooden deck, is visible in the background.

4.93 out of 5 average rating, 15 reviews

Hamptons Home w/ Salt Water Pool

3 Bed/ 2 Bath Sag Harbor Retreat w/ Salt Water Pool. Nestled close to both Sag Harbor Village and Sagaponack, this charming home offers the perfect blend of comfort and convenience. With 3 bedrooms, 2 baths, and situated on a generous .66-acre lot. Outdoors, the expansive yard features a 35x17 saltwater pool. Located just moments from Sag Harbor Village, you'll enjoy easy access to boutique shops, acclaimed restaurants, Wolffer Estate Vineyards, and picturesque waterfront views.

4.96 out of 5 average rating, 98 reviews

A modern living area features a light-colored sofa adorned with decorative pillows. A glass-topped coffee table sits in front, and light streams in from a nearby window. Exposed wooden beams draw attention to the ceiling, while shelves display curated décor against a neutral wall.

Cottage in The Hamptons

Steps to the Beach - Designer Cove House Cottage

All new modern interior and exterior furnishings by luxury interior designer. Enjoy fabulous water views on the expansive mahogany deck from this sweet beach cottage that was completely renovated and is a short walk to beautiful Long Beach and just a couple of miles to Sag Harbor's Main St. The home features an open floor plan, cozy gas fireplace, an updated kitchen with stainless appliances and Viking range. Three bedrooms (one with a private office) and an outdoor shower.

Guest suite in The Hamptons

A cozy sleeping area is highlighted by a spacious bed with light blue bedding, positioned near a working fireplace. A television is placed on a wooden stand across from the bed. Soft lighting from bedside lamps creates a warm ambiance, complemented by a decorative artwork on the wall.

4.9 out of 5 average rating, 392 reviews

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

4.93 out of 5 average rating, 136 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.

Flat in The Hamptons

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 .

A spacious backyard is featured, showcasing a stone fire pit surrounded by multiple white Adirondack chairs. Lush green grass extends towards a well-maintained home set against a backdrop of trees. The area provides a serene outdoor space for relaxation and gatherings.

4.85 out of 5 average rating, 40 reviews

Bridgehampton Designer Home w/ Pool + Pickleball

Just 2 miles from downtown Sag Harbor , 1 mile from downtown Bridgehampton. Ten minutes to the Ocean Beaches. Great for families, couples, solo adventurers, business travelers. NO PETS, NO SMOKING, NO PARTIES OR LARGE GROUPS,. RATES INCLUDE THE FOLLOWING: Electric , cable TV & wi-fi, propane consumption, telephone, trash removal, lawn & pool service and pool heater set to 85 degrees June 1 to LD.

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, 313 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.

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, 152 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 –

4.98 out of 5 average rating, 366 reviews

The living area features two comfortable sofas, a wooden coffee table, and a dining table set for four. A window allows natural light to fill the space, while decor accents create a relaxed environment. Air conditioning unit is visible on the wall.

Cottage in The Hamptons

Carriage House - Cottage in East Hampton Village

Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

4.95 out of 5 average rating, 73 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.

Popular amenities for Bridgehampton holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Bridgehampton

A welcoming living area features a comfortable sofa adorned with coral-patterned pillows. A rustic coffee table sits at the center, surrounded by natural light from large windows. A view of the open space and kitchen area can be seen in the background.

4.97 out of 5 average rating, 159 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

A gated patio area is surrounded by lush greenery, featuring tall plant hedges on one side. Two wooden arches frame the entrances, leading to a scenic garden path. A small seating area with a patterned cushion is set in the foreground, inviting relaxation.

5 out of 5 average rating, 5 reviews

Cozy Hamptons Cottage

4.96 out of 5 average rating, 103 reviews

The image showcases a spacious outdoor area featuring a heated gunite pool surrounded by manicured grass. Four loungers with umbrellas are positioned near the pool, while a cozy seating arrangement is visible on the patio. A charming cottage is seen in the background.

Cottage in The Hamptons

Modern Southampton Cottage | Heated Pool & Peloton

4.88 out of 5 average rating, 52 reviews

East Hampton Secluded Escape with Gunite Pool

Flat in The Hamptons

4.81 out of 5 average rating, 37 reviews

Peaceful getaway in the Hamptons

A spacious deck features outdoor dining and lounging areas under a blue umbrella. Lush greenery surrounds the home, with colorful shrubs and a rock accent visible in the foreground. Bright blue skies and soft clouds create a serene backdrop.

5 out of 5 average rating, 10 reviews

Brick Kiln

Apartment in The Hamptons

4.84 out of 5 average rating, 101 reviews

Cute cottage apartment upstairs in Sag

A refreshing swimming pool is framed by lush greenery and vibrant plants, enhancing the serene outdoor environment. Loungers are positioned beside the pool, inviting relaxation. The clear blue water reflects the sky, surrounded by stone and floral elements, creating a tranquil escape.