Holiday rentals with a patio in Wainscott

4.91 out of 5 average rating, 122 reviews

Walk to Water & Dining | Pool | 8 Min to Beach

Top 5% Airbnb properties! Escape to your serene, chic, Hamptons oasis. Perfectly located 1 block to waterfront dining + minutes to Main St Enjoy the luxury of your own home nestled in serenity + nature. You'll feel the calmness + zen @ this private property. Swim in your pool, BBQ + spark up the firepit. Walk just 1 block to Sisi, Buongiorno + Wayan for dinner, cocktails + coffee on the water… an ideal spot to watch the yachts + sunset. You'll be 8 mins. to Main St. shopping, beaches + more!

A clean and inviting sleeping area is presented with a spacious bed adorned with white bedding. Two decorative pillows are arranged on the bed, adding a touch of texture. A floor-length mirror and a slender arrangement of decorative branches enhance the modern aesthetic of the space.

5 out of 5 average rating, 19 reviews

NEW Private, modern centrally located Apartment!

Come stay with us at our private, modern, extremely clean airbnb! We pride ourselves on paying close attention to detail, and going above and beyond to ensure our guests have the best experience. You will have your own private unit with a private back patio and parking spot. Nothing is shared) We are centrally located just 5 minutes of beautiful East Hampton Village and Amagansett village. We are also 1.5 miles from the closest beach. (beach pass not included or transferable as per town lawslyyw

4.86 out of 5 average rating, 134 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!

4.93 out of 5 average rating, 122 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.

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.

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

4.99 out of 5 average rating, 110 reviews

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.

A serene river scene is captured under a partly cloudy sky. Tall grasses line the water's edge, while trees provide shade along the bank. The calm water reflects the surrounding landscape, creating a peaceful atmosphere.

4.92 out of 5 average rating, 13 reviews

Private Beach Community with exceptional light

Kick back and relax in this calm, light filled home in Lionshead’s Private Beach Community. Paddle right out off your backyard. Enjoy organic garden vegetables, feed the swans. Kayac into the sunsets or sit by a gorgeous fireplace.This is a NO SMOKING , no vaping and no party home. If you are intending to travel with your dog please let us know prior to your arrival and ask for permission. We are very dog friendly but would love to know what kind of dog and will decide ASAP

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.

4.88 out of 5 average rating, 51 reviews

East Hampton Secluded Escape with Gunite Pool

Elegantly furnished 4 bedroom house on lushly landscaped grounds, fewer than 5 minutes from the heart of East Hampton Village. This home is ideal for outside living, featuring a gunite, in-ground salt-water pool and stone patio. The interior is bright and spacious, accented by minimalist yet warm furnishings. Common living areas include a large family room with TV, large dining room with gas fireplace, and a large eat in kitchen. Rental registry HMT23-10468

4.98 out of 5 average rating, 55 reviews

A spacious living area is highlighted by a stone fireplace, flanked by large windows that provide ample natural light. Wooden beams run across the ceiling, complementing the neutral-toned furnishings, including a cozy sofa. A dining table is visible in the background, surrounded by greenery.

Cottage in The Hamptons

Chic cottage on lush, secluded acre by the beach.

Charming cottage with spacious lawn surrounded by lush vegetation and protected land. 5-minute walk to a secluded and serene Northwest Harbor beach. An approximately 10-minute drive from both East Hampton and Sag Harbor restaurants and stores. Chic and modern rooms with brand-new, high-end bathrooms. Perfect rental for those who want a mix of quiet time and quick access to everything else. Relax and unwind at this unique and tranquil getaway.

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.

4.99 out of 5 average rating, 128 reviews

Winter Getaway 2 miles from 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.

A private swimming pool reflects clear blue skies, surrounded by lounge chairs and umbrellas. Lush greenery frames the scene, while a wooden deck leads to the main house, which features a modern architectural design. A swing set adds an element of leisure to the serene outdoor space.

4.93 out of 5 average rating, 44 reviews

¤¤¤ Wonderful retreat on 4 acres with pool ¤¤¤

Private, calming, and stylish Hamptons retreat—the ultimate escape from the city. Enjoy an inviting swimming pool from the surrounding hammock, lounge chairs, and swing. The best of indoor-outdoor living is steps away on the wraparound deck featuring an outdoor kitchenette with BBQ, a large outdoor dining table with seating for 12, and an outdoor gas-powered fireplace. All this against the backdrop of 4 acres of private forest greenery.

A charming house is presented, featuring a blend of shingled and brick exterior. The porch is outlined by neatly trimmed hedges, and a gravel pathway leads to the entrance. Lush greenery surrounds the home, accentuating its inviting curb appeal.

4.94 out of 5 average rating, 34 reviews

East hampton 3 bedroom home w/ pool great location

Welcome to your hamptons summer home! Amazing location 5 minutes from both Sag Harbor and East Hampton towns and 10 minutes to Bridge Hampton. Beautifully landscaped backyard with heated pool and bbq. The primary bedroom includes a king bed, the 2 secondary bedrooms have queen beds. Open floor plan with kitchen and dining room flowing to the backyard is perfect for indoor/outdoor lunch and dinners. 2 full bathrooms and central air.

Popular amenities for Wainscott Holiday Houses with Outdoor Verandahs

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.98 out of 5 average rating, 80 reviews

The charming two-story building features a light-colored exterior with shingle accents. A covered porch spans the front, supported by tall white columns. Large windows invite natural light, while blooming trees enhance the inviting street view.

Apartment in North Fork

Newly Renovated 2-BR Apartment

5 out of 5 average rating, 16 reviews

Apartment in North Fork

Tranquil country garden retreat

5 out of 5 average rating, 10 reviews

Apartment in Mastic

South Shore Studio

4.84 out of 5 average rating, 31 reviews

2Br Hampton Family Escape: Beaches, kayaks, BBQ

A serene sleeping area features a light-colored headboard and a white comforter layered with decorative pillows. Natural light filters through white curtains, and a round mirror enhances the space. A tall vase with dried branches adds an elegant touch.

4.83 out of 5 average rating, 76 reviews

NEW- Private Modern East Hampton Apartment!

The exterior of a spacious two-story home is shown, featuring a light beige façade and large windows. A set of white steps leads to the front door, flanked by neatly maintained shrubs. The property includes a two-car garage and a paved driveway.

5 out of 5 average rating, 16 reviews

The Hamptons

A cozy living area features a comfortable sofa adorned with neutral-toned cushions. A large television is mounted on the wall. Natural light filters through multiple windows, brightening the space. A small side table and an armchair complement the seating arrangement, creating an inviting atmosphere.

5 out of 5 average rating, 26 reviews

Southampton apt walk to village

Apartment in Center Moriches

An open studio space features a spacious bed with a light duvet and decorative pillows. A leather couch complements the area, while large windows provide natural light, framed by white blinds. A bedside table and warm lighting create a cozy ambiance.

4.82 out of 5 average rating, 109 reviews

Cozy Studio 15 Min From Hampton Beaches

Holiday House Rentals with a Verandah

5 out of 5 average rating, 44 reviews

A spacious backyard is featured, with a circular stone fire pit surrounded by several colorful Adirondack chairs. Lush green grass extends towards a charming white house in the background, bordered by trees under a clear blue sky.

Home in Southold

Private Waterfront Access + Hot Tub + Scenic Yard

5 out of 5 average rating, 4 reviews

Home in Southampton

Stunning Southampton Star

A modern round house stands prominently, featuring large windows that allow natural light to illuminate the interior. The exterior showcases a sleek design and is surrounded by a landscaped area, providing a serene and inviting entrance. Two chairs are positioned on the front porch.

4.78 out of 5 average rating, 27 reviews

Rare ROUND home in E.H - salt water pool & hot tub

The exterior of the artist's beach cottage features a charming facade with wood shingles and well-maintained landscaping. A welcoming front porch is flanked by shrubs and flower beds, while a serene lawn leads toward a lush backyard visible in the distance.

4.91 out of 5 average rating, 53 reviews

Classic Hamptons Cottage - Heart of Amagansett

4.9 out of 5 average rating, 20 reviews

A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.

Home in Southold

Stylish Beach Getaway: pool & walking location

A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.

5 out of 5 average rating, 50 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

A spacious saltwater pool is surrounded by a well-manicured yard, featuring lounge chairs and large umbrellas. Water features create gentle splashes, enhancing the serene environment. The area is framed by trees, providing a natural backdrop for relaxation.

4.98 out of 5 average rating, 100 reviews

Brand new house with an all year round hot tub.

5 out of 5 average rating, 20 reviews

The exterior of a renovated cottage is displayed, featuring light green siding and white trim. Large windows invite natural light, while a welcoming front porch is framed by greenery. A gravel pathway and well-maintained landscaping enhance the peaceful setting.

Home in North Fork

Beautiful 1930s 4 bed 3 bath! Walk to Beach

Holiday condos with a patio

Lounge chairs are arranged around a patio area, each shaded by a large umbrella. A potted plant adds a touch of greenery, and a serene body of water is visible in the background, bordered by lush vegetation and a wooden fence.

4.67 out of 5 average rating, 3 reviews

One Bedroom Apartment Nestled in the Dunes

5 out of 5 average rating, 6 reviews

Condo in Greenport

Greenport Getaway at Cliffside Condos

A bright living area is furnished with a light-colored sofa, floral-patterned chairs, and a coffee table with decorative items. A large television is positioned on a dark wooden console. Natural light filters in through windows, illuminating the space with a cozy ambiance.

Charming Bayfront Condo

A bright and colorful room features bold stripes in green, orange, and purple on the walls. A spacious bed with white linens and pink accent pillows is positioned near a window. A spiral staircase leads to an upper level, complementing the room's playful design.

Charming 2 Bedroom Apartment with Beach Amenities!

An aerial view displays the condo complex adjacent to the waterfront, featuring a central pool surrounded by a landscaped patio. The blue ocean extends beyond the property, with boats visible in the distance under a clear sky, enhancing the serene coastal environment.

4.94 out of 5 average rating, 34 reviews

Sun N Sound Resort, Montauk, NY

A spacious studio is shown, featuring a king-size bed with crisp white linens. Natural light floods the room through large sliding doors that open to a private balcony with views of the waterfront. A ceiling fan hangs above, and a sitting area with a green sofa is present.

4.9 out of 5 average rating, 10 reviews

Endless Summer Studio Condo w Balcony Bayview

A vivid sunset is captured over the water, with orange and yellow hues radiating across the sky. A calm sea reflects the colors, while a small blue structure stands near the shore, overlooking the scene. A wooden boardwalk leads toward the gentle waves.

4.54 out of 5 average rating, 24 reviews

Immersed in Montauk's Mesmerizing Waterfront Bliss

A modern kitchen space features stainless steel appliances and white cabinetry. A spacious island with a sink provides a functional area for meal preparation. Natural light floods the room, highlighting the dining area with a view of the water through sliding glass doors.