Holiday houses in Bridgehampton

5 out of 5 average rating, 61 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 The Hamptons

Luxury Gem At The Heart of Sag Harbor Village

An impeccably renovated, luxury cottage at the heart of Sag Harbor village. Walkable within minutes to the downtown shops, restaurants, marinas and local beach! In one of the most coveted historic streets, enjoy this two-bedroom house, its large living & dining rooms, two fireplaces, designer kitchen (and latest appliances). Countless details and gorgeous wide planked floors, mixed with technology throughout the house. The private backyard has a brick patio, landscaped garden and outdoor shower.

4.88 out of 5 average rating, 114 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

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, 198 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 historic white building with multiple stories is depicted, featuring classic architectural details and a large front porch. An American flag is displayed prominently in front. Lush green grass and neatly trimmed hedges surround the property, enhancing its inviting exterior.

4.84 out of 5 average rating, 70 reviews

Beachside Escape from NYC

Topping Rose House has been standing on the same intersection of Montauk Highway in Bridgehampton since 1843. The hotel was renovated and reopened in 2012 and is now the preeminent place to feel like a Hamptonite. In the summer, relax by the pool or bike to the Atlantic. In the winter, enjoy the stunning landscape of the villages of the Northeast. The hotel has 22 rooms, and is only listing on AirBnB for a limited time. The specific room type is assigned on the day of arrival.

4.77 out of 5 average rating, 108 reviews

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

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.

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, 381 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. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

4.98 out of 5 average rating, 48 reviews

Villa in The Hamptons

SERENITY AT SHOREWOOD 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.

A bright living area features a white sofa adorned with patterned blue pillows, positioned beside a rustic wooden coffee table. Large glass doors open to reveal a glimmering pool and lush outdoor landscaping, enhanced by vibrant potted plants and a shaded seating area.

4.89 out of 5 average rating, 134 reviews

Serene 3 Bed 2.5 Bath House w/Heated Pool

Situated off a quiet lane on a half-acre, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 3 wonderful bedrooms 2 modern bathroom and a heated saltwater pool ( See Pool heat and Pool Closure Details ) with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

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, 147 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 – no exceptions!

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, 307 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 wide sandy beach stretches towards the horizon, where soft waves gently lap at the shore. Tall lifeguard stands are positioned along the beach, with a few distant figures walking. The sky features a gradient of muted colors as the sun sets, creating a serene atmosphere.

4.95 out of 5 average rating, 225 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

A light-filled living area features a comfortable sectional sofa with decorative pillows. A coffee table rests on a textured area rug, accompanied by framed art on the white walls. Natural light enters through a window overlooking greenery, accentuating a serene environment.

4.92 out of 5 average rating, 52 reviews

Spacious One Bedroom Apartment, Close to Beaches

One bedroom apartment with large king bed, double sink vanity, full kitchen, private entrance, and close proximity to town and beaches. Parking on premises, access to washer/dryer for long term guests. Centrally located between Southampton and Sag Harbor. Air mattress must be requested. 1.5 miles to the bay beaches 5 miles to closest ocean beaches

Popular amenities for Bridgehampton holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Bridgehampton

4.9 out of 5 average rating, 39 reviews

The exterior of a modern cottage is presented with a black wood facade and multiple windows. A front porch is seen, partially enclosed with slatted wood. Lush green grass and shrubbery frame the entrance, creating a welcoming approach to the home.

Home in North Fork

Waterfront NoFo Cottage w/ public beach access

A tranquil outdoor space features a heated pool surrounded by neatly manicured grass and various lounge chairs. The stylish home in the background showcases a spacious deck with striped umbrellas, creating inviting areas for relaxation and enjoyment amidst lush landscaping.

4.94 out of 5 average rating, 17 reviews

Breathtaking Sag Harbor 5 bed 6 bath-Heated Pool

5 out of 5 average rating, 44 reviews

A charming cottage exterior is surrounded by vibrant pink and purple hydrangeas. A well-maintained stone pathway leads to double doors adorned with seasonal wreaths, framed by natural greenery. The textured shingle siding adds a rustic element to the inviting entryway.

Cottage in The Hamptons

Charming Cottage in Sag Harbor

A charming cottage is surrounded by lush greenery and colorful flowers. A wooden deck with a large umbrella provides shaded seating. The exterior features grey shingle siding and several windows, allowing natural light to enhance the inviting appearance of the home.

4.89 out of 5 average rating, 83 reviews

Charming Water Mill Cottage

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, 10 reviews

Peaceful cottage

A spacious living area features a modern sectional sofa with decorative pillows and a cozy rug. A wall-mounted television is positioned opposite the seating, and natural light filters in from a window, highlighting the room's neutral color palette.

Condo in The Hamptons

4.84 out of 5 average rating, 98 reviews

Cute cottage apartment upstairs in Sag

Luxe

A large outdoor area includes a heated pool surrounded by loungers and umbrellas. A spacious lawn is complemented by a deck and lush greenery, enhancing the serene setting. The house features a classic design with white siding and multiple windows for natural light.

5 out of 5 average rating, 5 reviews

Ideal September Home w/ Heated Pool. Sag &Bridge.

A cozy living area features a green patterned accent wall and a comfortable sofa. A television is positioned on a white media stand, while a rustic dining table and chairs are present. A bright red fridge adds a pop of color, and a lofted sleeping area is accessed by a blue-painted staircase.