Vacation rentals in Westhampton

4.93 out of 5 average rating, 178 reviews

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.

Cottage in The Hamptons

Chic Artist Loft Cottage

We loved all things SEA…my family built this special Artist Loft Tiny Cottage Retreat. Over the years, family & guests have created beautiful memories here. The Cottage has a large fenced yard, & deck. The inside is an open layout, light and airy. It is very clean and designed with care. The living rm area has a sleeping sofa with a staircase to the loft that has a platform bed and a tiny twin cot. The kitchen is fully equipped & there is a full bath & W/D. 1 mile to Main St/1.5 mi. to Beaches.

4.87 out of 5 average rating, 101 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!

Guesthouse in The Hamptons

A private outdoor space is showcased with a wooden deck, featuring two lounge chairs and a dining table shaded by an umbrella. Potted flowers add color, while a path leads through the well-maintained garden, enhancing the serene atmosphere of the yard.

4.97 out of 5 average rating, 209 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.

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

4.97 out of 5 average rating, 126 reviews

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully fenced tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

4.93 out of 5 average rating, 101 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 North Fork

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.

4.97 out of 5 average rating, 176 reviews

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Superhost

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

4.85 out of 5 average rating, 113 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

4.95 out of 5 average rating, 132 reviews

A cozy living area features a plush gray couch adorned with decorative pillows. Vibrant blue walls complement the stylish kitchen cabinetry in the background. A large flat-screen television displays a scenic beach image, while a sleek desk sits nearby. Soft lighting adds to the inviting ambiance.

Apartment in Shirley

Boho Beach Vibez Retreat! Private entrance

"Experience a different kind of stay with our unique Airbnb, the 'Boho Beach Vibez” This cozy 1-bedroom apartment , that’s approximately 500sqft is situated on the first level of our home with a separate entrance . Located in a prime area of our town, you'll find yourself just minutes away from all the stores, restaurants, highways, and within walking distance of hiking trails, the Carman’s river, and 5 miles from Smith Point beach. NOTE : hosts live on top level .

A spacious living area is illuminated by natural light from large windows. A comfortable sofa and armchair are arranged around a low coffee table. A dining table with six chairs sits adjacent, while the kitchen is visible in the background. A staircase leads to the upper floor.

4.94 out of 5 average rating, 142 reviews

Modern 5BR Getaway • Close to Beaches & Wineries

⭐ Rated 4.95 with 135+ glowing reviews! This modern 5BR, 4BA Hampton Bays retreat sleeps 10 and is just minutes from beaches, dining, and shops. Enjoy open living spaces, Smart TVs, and fast WiFi. The finished basement features ping pong, a gym, and lounge, while the backyard offers a BBQ, patio, and outdoor seating. Beach gear is included, making it easy to explore. Perfect for families or groups seeking the ultimate Hamptons getaway with comfort and style.

4.94 out of 5 average rating, 127 reviews

A spacious room features a queen-size bed adorned with a light gray quilt. Bedside tables with lamps flank either side, and a decorative bench sits at the foot of the bed. Natural light filters through the sheer curtains, enhancing the calming color palette.

Apartment in North Fork

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

Welcome to Jeanette and Jims Airbnb! We are avid travelers and look forward to hosting you on your trip to beautiful Long Island! Lovely, clean updated private room with private separate entrance and bathroom. Great location on a quiet wooded acre. 2 miles from Splish Splash. 3.6 miles from the Long Island Aquarium. 8.7 miles from Cupsogue Beach. 4.8 miles from Baiting Hollow Farm Vineyard. So much to do near by. Head easily to the north or south fork!

A contemporary ranch-style home is surrounded by lush greenery. The custom-shaped heated pool features a waterfall and is bordered by a stone patio with lounge chairs and umbrellas. A state-of-the-art hot tub is positioned nearby, enhancing the outdoor relaxation space.

4.93 out of 5 average rating, 159 reviews

Hampton's Haven

5 bedroom, 3.5 bath contemporary ranch style home, with custom shaped heated pool and meticulously maintained 7 seater hot tub. Expansive patio w/outdoor dining for 10 - close to beach, town and more! Our home has comfortable office space with gigabit wifi throughout! Fabulous game room with ping pong, 4 person air hockey, smart tv and board game lounge. Everything you'll need for a memorable gathering of friends or the perfect family vacation!

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

4.99 out of 5 average rating, 148 reviews

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

Popular amenities for Westhampton vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Westhampton oceanfront boutique hotels

An inviting porch area features a hanging chair and wicker details. Colorful plants line the railings, complementing the white exterior of the building. A weather vane adorns the roof, while sunlight casts soft shadows on the patterned floor, creating a serene outdoor space.

Hero Double, Hero Beach Club, Next to the Beach

An aerial view captures the beachside property nestled beside a sandy stretch, where several white umbrellas are arranged on the beach. The surrounding landscape features green vegetation and a serene body of water in the background, reflecting the clear blue sky.

Hero King Deluxe, Hero Beach Club, Beachfront

An aerial view reveals the outdoor swimming pool surrounded by loungers and umbrellas, with a backdrop of lush greenery and the road. The American flag is prominently displayed, and the peaceful atmosphere is enhanced by the nearby waterway.

Hero Double Oceanside, Hero Beach Club, Pool

A modern hotel room is highlighted by a spacious queen bed adorned with decorative pillows. Natural light filters through a window, complemented by a wall-mounted lamp. A woven wall hanging adds texture, while a light-colored blanket drapes across the bed, providing a serene atmosphere.

Hero Queen, Hero Beach Club, Steps from the Beach

An aerial view captures the outdoor pool area featuring several loungers and umbrellas, surrounded by lush landscaping. The clear blue water contrasts with the surrounding greenery and nearby houses. A flag gently flutters in the breeze, adding a touch of Americana to the serene setting.

4.85 out of 5 average rating, 179 reviews

2 Hero Double, Hero Beach Club, Near Montauk Dunes

Westhampton oceanfront vacation rentals

Superhost

A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.

Cabin in Shirley

A-Frame cabin with private beach & epic sunsets

4.98 out of 5 average rating, 224 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

4.99 out of 5 average rating, 107 reviews

An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.

Cottage in Guilford

Waterfront Joshua Cove Cottage with private beach.

A dining set featuring a large wooden table with eight matching chairs is positioned under a spacious umbrella, offering shade. Lush greenery and a serene waterfront view are visible nearby, providing a peaceful outdoor setting.

4.98 out of 5 average rating, 104 reviews

Breezy Waterfront Home With private Dock

4.88 out of 5 average rating, 150 reviews

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 North Fork

Waterfront Autumn Escape in Wine Country: 2BR

4.94 out of 5 average rating, 157 reviews

A well-maintained putting green is positioned in the front yard, surrounded by soft turf and bordered by gravel. Small flags are placed on the green, with nearby shrubs and trees adding to the outdoor landscape. The house is visible in the background.

Home in Shirley

Beach Waterview, 3 KING Beds, Golf Putting Green

5 out of 5 average rating, 104 reviews

A lush backyard features a children's playset alongside a hammock. Adirondack chairs are arranged around a fire-pit, framed by trees and greenery. A serene waterfront view is visible, with a dock extending into the calm waters, enhancing the natural landscape.

Villa in The Hamptons

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

A serene waterfront view features a sailboat gliding across calm waters. Lush green grass borders the shoreline, reflecting the tranquility of the environment. The clear blue sky stretches overhead, enhancing the peaceful atmosphere of the setting.

5 out of 5 average rating, 138 reviews

Hamptons Waterfront- Great Location- On the bay

Other great vacation rentals in Westhampton

The exterior of the home features a well-maintained front lawn, showcasing lush green grass and a variety of garden plants. The house's white facade is complemented by light wooden shutters, and a charming front porch with seating is visible to the left.

5 out of 5 average rating, 12 reviews

Private, Family Friendly Home in the Heart of WHB

5 out of 5 average rating, 9 reviews

Chic Hamptons Retreat | Fireplace, Hot Tub, Beach

4.93 out of 5 average rating, 102 reviews

An open living space is presented, featuring a modern kitchen with stainless steel appliances and a white circular dining table surrounded by black chairs. A large television is mounted on a white cabinet, and light enters through a nearby window.

Cottage in The Hamptons

Hamptons Cottage.

Farm stay in The Hamptons

A serene outdoor landscape showcases a well-manicured lawn, framed by lush greenery and colorful flowers. In the background, a fenced area contains a barn and a horse, while a vegetable garden with trellises is visible to the right.

5 out of 5 average rating, 12 reviews

The Snug on the Farm ~ Cozy cottage home

5 out of 5 average rating, 31 reviews

The image captures a spacious outdoor area featuring a large, heated swimming pool surrounded by lounge chairs. A well-maintained lawn is visible, along with a charming cottage that includes an inviting porch. Lush greenery and trees form a serene backdrop.

Cottage in The Hamptons

Newly built cottage near the bay and hamptons

4.98 out of 5 average rating, 93 reviews

Brand new house with an all year round hot tub.

Apartment in The Hamptons

A spacious room features a large bed with a green accent blanket and a simple headboard. Natural light flows in through a large window, offering a view of greenery outside. A light wood dresser and minimalist decor complete the serene atmosphere.

4.88 out of 5 average rating, 8 reviews

Stay in Westhampton for Less

A bright and airy living space features a cozy beige sofa facing large windows with water views. A staircase leads to the upper level, and natural light illuminates the open layout. Light-colored furniture and decorative accents create a relaxing coastal ambiance.