Vacation rentals in The Hamptons

A charming cottage is illuminated warmly at night, showcasing a welcoming entrance. A well-lit pathway lined with soft ground lights leads toward the front door, framed by the surrounding wooded area. The exterior features a classic design, with wooden siding and inviting windows.

4.95 out of 5 average rating, 254 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

4.91 out of 5 average rating, 128 reviews

Serenity + privacy; 1 block to waterfront dining

Enjoy the privacy and serenity of your own home! Located near all of the best Hampton's attractions. Enjoy your large home surrounded by nature and calm vibes. Swim in your pool, spark up the BBQ + firepit, enjoy al fresco dining under the stars. Stream your 80' TV + cook in your large Chef's kitchen. Stroll just 1 block to the best waterfront dining + cafe for dinner/drinks/coffee on the sea. You will be 8 mins to Main St., 10 mins to beaches, close to museums, coffee shops + so much more!

4.96 out of 5 average rating, 495 reviews

The interior of the cabin features a spacious bed framed by large windows that invite natural light. A small dining table is set beside a plant, and the wooden ceiling enhances the cozy ambiance. A decorative blanket adds a splash of color to the bed.

Cabin in Montauk

Tiny Cottage in Hither Woods, Montauk

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

4.86 out of 5 average rating, 145 reviews

Home in Hampton Bays

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!

Guesthouse in Hampton Bays

A private outdoor deck features two lounge chairs facing toward a lawn, accompanied by a round dining table with four chairs and an umbrella for shade. Surrounding greenery provides a serene setting, complemented by wooden siding on the cottage's exterior.

4.97 out of 5 average rating, 219 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

Guesthouse in East Hampton

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.

4.99 out of 5 average rating, 111 reviews

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.

4.98 out of 5 average rating, 173 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Home in Westhampton Beach

A modern living area features a spacious sectional sofa adorned with soft pillows. A flat-screen TV is mounted on the wall, displaying an underwater scene, while a cozy fireplace adds warmth. Natural light filters through multiple windows, offering a view of the outdoors.

4.97 out of 5 average rating, 104 reviews

Brand new house with an all year round hot tub.

Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

Apartment in Hampton Bays

A calm waterfront scene shows a serene body of water reflecting the sky. A sandy beach is visible, framed by natural vegetation, with a wooden barrier along the shoreline. The peaceful setting invites relaxation and enjoyment of the outdoors.

4.97 out of 5 average rating, 418 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

4.99 out of 5 average rating, 116 reviews

Home in Montauk

3 BR/Pool. Walk to Beach & Town!

Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Guest suite in Sag Harbor

An inviting outdoor sitting area features wooden chairs positioned near French doors. The space is surrounded by lush greenery, and a stone pathway leads to the entrance of the studio apartment. Flowering vines and potted plants add a touch of nature.

4.9 out of 5 average rating, 395 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.

Guest suite in East Hampton

An inviting in-ground pool is surrounded by lush greenery and vibrant trees. Sunlight reflects off the clear blue water, enhancing the serene atmosphere. Outdoor seating can be seen nearby, providing a tranquil spot to relax amidst the natural setting.

4.9 out of 5 average rating, 252 reviews

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

Popular amenities for The Hamptons vacation rentals

Gym

Private vacation rentals in The Hamptons

5 out of 5 average rating, 28 reviews

Apartment in Montauk

Dockside 2BR - Prime Location on the Marina Unit B

5 out of 5 average rating, 59 reviews

Cottage in Sag Harbor

Charming Cottage in Historic Sag Harbor

A spacious deck surrounds a heated pool, featuring a light blue surface reflective of the sky. Four sun lounge chairs are positioned for relaxation, and an outdoor dining area with a retractable awning is available. Lush trees provide a natural backdrop to the serene setting.

5 out of 5 average rating, 75 reviews

East Hampton Rental w/ Pool, Moments to Amenities

4.94 out of 5 average rating, 178 reviews

1800 Historical EH Home, 1 Mile to Town!

4.94 out of 5 average rating, 50 reviews

Sparkling East Hampton Oasis 3/2, heated pool

4.97 out of 5 average rating, 75 reviews

The cottage features a charming exterior with light-colored walls and green shutters. A welcoming entrance is highlighted by a gabled roof and steps leading to the door. Lush greenery surrounds the property, complemented by well-maintained flowerbeds and a stone pathway across a manicured lawn.

Cottage in Water Mill

Head of Pond House - Waterfront Cottage

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

4.98 out of 5 average rating, 137 reviews

Explore the Water & Woods at a Relaxing Retreat

5 out of 5 average rating, 7 reviews

The exterior of a spacious two-story house is highlighted, surrounded by lush greenery. A clear saltwater pool features a light blue hue, with several lounge chairs positioned along the patio. Large windows adorn the house, inviting natural light into the interior.

Home in Sag Harbor

Designer home in Sag Harbor : 5BR walk to beach

The Hamptons beach vacation rentals

4.97 out of 5 average rating, 263 reviews

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

Designer Beach Retreat on Exclusive Cedar Beach

4.97 out of 5 average rating, 229 reviews

An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.

Home in Shirley

Luxurious Waterfront Beach House On The Bay

4.9 out of 5 average rating, 183 reviews

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

Condo in Greenport

Beautiful Waterview Condo on the North Fork of LI

4.88 out of 5 average rating, 103 reviews

A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.

Cottage in Milford

Cheerful 3 Bedroom Cottage with Fire Place

4.86 out of 5 average rating, 116 reviews

A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.

Cabin in Riverhead

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Superhost

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

Condo in Greenport

4.88 out of 5 average rating, 161 reviews

Waterfront Escape | Private Beach, Pool & Views

4.89 out of 5 average rating, 151 reviews

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.

Condo in Greenport

Beachside Waterview 2Br Condo w/ Pool in Greenport

4.94 out of 5 average rating, 185 reviews

An aerial view captures the serene neighborhood, showcasing small homes interspersed with trees and greenery. The bay can be seen in the distance, along with the nearby beach access. The well-maintained grounds of the property highlight a clean, welcoming environment.

Home in Shirley

Waterview Beach House: 3 Kings + Putting Green

Family friendly vacation rentals in The Hamptons

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

4.92 out of 5 average rating, 128 reviews

Private & Pristine with Pool and Kid’s Playard

Cottage in Westhampton Beach

A spacious lawn is surrounded by trees, creating a private outdoor area. Several seating arrangements are present, including wooden benches arranged around a fire pit. The cottage, featuring light-colored siding and decorative elements, is visible in the background under clear blue skies.

4.93 out of 5 average rating, 184 reviews

Chic Artist Loft Cottage

Guesthouse in East Hampton

The exterior of the cottage is surrounded by lush, vibrant greenery, with climbing plants and flowering shrubbery. Natural light illuminates the soft colors of the cottage, which features multiple windows and a door framed by greenery, presenting an inviting and tranquil setting.

5 out of 5 average rating, 11 reviews

Enchanting studio cottage, walk everywhere

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.

4.89 out of 5 average rating, 56 reviews

East Hampton Secluded Escape with Gunite Pool

The backyard showcases a serene oasis with a sparkling pool surrounded by lush greenery. A sunroom is visible, providing a view of the inviting outdoor space. The setting offers a sense of privacy, enhanced by the natural landscape.

4.95 out of 5 average rating, 96 reviews

Oasis backyard, Pool, Gym, and Sunroom!

4.93 out of 5 average rating, 105 reviews

A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.

Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

5 out of 5 average rating, 26 reviews

Home in Southampton

Dream Colonial with Heated Pool Southampton, NY