Cottage holiday rentals in Southampton

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.

4.96 out of 5 average rating, 100 reviews

Modern Southampton Cottage | Heated Pool & Peloton

Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers 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, 182 reviews

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.

A light blue house features a welcoming front porch with bright blue chairs. The well-maintained lawn is surrounded by a white picket fence and shaded by a leafy tree. A gravel driveway leads to the garage, creating an inviting outdoor space.

4.93 out of 5 average rating, 167 reviews

Montauk Cottage Escape

EH Town Rental Registry: 23-483 Escape to Montauk’s Quiet Side- Enjoy the peaceful beauty of Montauk in the off-season from this updated, spacious, comfortable home - close to town, beaches, and scenic trails. Between cozy nights in and crisp coastal walks, this is the perfect retreat for a weekend getaway or a work-from-home reset. Reliable Wi-Fi and a fully equipped kitchen make it easy to settle in for a few days—or weeks. Dogs are welcome with prior approval (Additional pet fee applies.)

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.

4.98 out of 5 average rating, 167 reviews

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.

A spacious living area features high ceilings and natural light streaming through large windows. A white sofa is paired with wooden chairs, while a glass coffee table sits on a woven rug. An elegant dining area is visible in the background with a large table.

4.96 out of 5 average rating, 166 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

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.

4.76 out of 5 average rating, 106 reviews

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.

4.94 out of 5 average rating, 253 reviews

A spacious living area displays rustic log walls and a mix of wooden and upholstered furniture. A comfortable leather sofa is positioned near a stone wood stove, while a colorful armchair adds charm. Natural light fills the room through windows adorned with patterned curtains.

Cottage in Patchogue

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

A bright living area features a spacious sectional sofa adorned with blue pillows, positioned near large windows that offer panoramic views of the water. A rustic coffee table adds a touch of charm, while the light-colored walls create a serene ambiance.

4.88 out of 5 average rating, 250 reviews

Waterfront Cottage, Fort Pond MTK

Perfect cottage perched above Fort Pond with epic views and relaxed bohemian vibes. The cottage is private with a private deck on shared grounds with a fire pit, hammocks, paddle boards, kayak, and lake access. The grounds are expertly landscaped and take full advantage of fort pond views. We do live on the property full time and enjoy making our space a safe and clean environment.

The living room features a bright and airy arrangement with a large white sectional sofa and a coffee table at the center. Natural light streams through the wide windows, creating a welcoming environment. A front door and a lamp add to the cozy feel of the space.

4.91 out of 5 average rating, 141 reviews

Hamptons Cottage 3-minute walk to breezy bay beach

Bright, airy 3 bedroom classic Hamptons cottage less than a block from bay beach which is perfect temp and temperament for swimming, wading, paddleboarding and kayaking. Sunsets over the Peconic Bay are amazing especially when you do it with a cold beverage at Tiki Joe’s which has food, drink and fun bands every summer night—only a short stroll away.

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.

4.97 out of 5 average rating, 353 reviews

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).

4.9 out of 5 average rating, 185 reviews

An open living space features wooden walls and bright hardwood floors. A cozy seating arrangement includes a sofa and a side table. A dining area with blue chairs is visible next to a large window, while a brick fireplace adds a rustic touch to the room.

Cottage in South End

Cozy Cottage on the Great Pond near beach.

In the heart of wine country is the adorable , nautical inspired cottage surrounded by nature, on a beautiful freshwater pond, a quick walk or bike ride away from a beautiful beach on Long Island Sound. Hiking, fishing, wine tours, farmstands abound!

A portable cabana is placed on a sandy beach with a view of the ocean. Two blue beach chairs are positioned underneath the cabana, providing shade. The shoreline and gentle waves are visible in the background, framed by a clear blue sky.

4.93 out of 5 average rating, 105 reviews

Amagansett Dunes Gem

Brand new to rental market, this beach cottage is 2 blocks to a private beach. newly updated kitchen and bath. large, fenced backyard with a fireplace is perfect for families with children and/or small pets. rental registry 16-3093

Popular amenities for Southampton cottage rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A spacious dining area features a long wooden table surrounded by several chairs. A large pendant light hangs above, casting soft illumination. Colorful wall accents and artwork complement the warm wooden flooring, while an adjacent kitchen can be seen in the background.

3 bedroom Hamptons cottage 5 mins from beach

The exterior of a charming cottage showcases natural wooden shingles, surrounded by lush greenery and vibrant shrubs. A wooden staircase leads to a covered porch, where large windows allow glimpses of the interior. The serene outdoor environment evokes a peaceful setting.

5 out of 5 average rating, 10 reviews

Walk/Bike to East Hampton Village & Ocean Beaches

A charming red cottage is framed by lush greenery, set back from a driveway leading to the entrance. A small white bench is visible on the left side of the well-maintained lawn, with flowering plants adding a touch of color in front of the house.

4.68 out of 5 average rating, 207 reviews

Lovely 2 BR Beach House No. Shore

An expansive wooden deck is depicted, surrounded by greenery. Low wooden planters are positioned along the railing, providing a natural element. The clear blue sky and subtle hints of the bay can be seen in the distance, creating a serene outdoor space.

4.84 out of 5 average rating, 31 reviews

4 Br Beach House; Short Walk to Beach!

5 out of 5 average rating, 9 reviews

The living area features a comfortable sofa adorned with a striped throw, a coffee table, and a television. Nearby, a dining space is set for meals, with natural light illuminating the room through large windows framed by light curtains.

Cottage in Bellport

Bellport Inn, Charming Cottage in the Village!

Private room in The Hamptons

A serene backyard is showcased, featuring a stone patio, a vibrant flower garden in colorful pots, and a tranquil pond with a water feature. A hammock is suspended between two trees, offering a relaxing spot surrounded by greenery.

4.83 out of 5 average rating, 109 reviews

Private Room in the House that Art Built

4.93 out of 5 average rating, 27 reviews

A large gunite pool is surrounded by a well-maintained grassy yard, featuring comfortable lounge chairs on a sunbathing area. Lush trees provide shade, while a charming cottage stands in the background, contributing to a serene outdoor setting.

Cottage in Bellport

Renovated Historic Cottage w/ Pool Bellport Vllage

An open-concept living space features a modern dining area with a wooden table set for six, complemented by sleek metallic chairs. A comfortable sectional sofa is positioned across from a wall-mounted television, with a fireplace and green outdoor views visible through large windows.

4.95 out of 5 average rating, 96 reviews

Calf Creek Cottage (Water Mill/Bridgehampton)

Pet-friendly cottage rentals

The exterior of a charming cottage is viewed, characterized by a light yellow façade and large windows. A brick patio features a round table with two chairs, surrounded by greenery. The area is well-lit by natural sunlight, contributing to a welcoming atmosphere.

4.78 out of 5 average rating, 23 reviews

Seabreeze #3: Cozy cottage by the beach

A bright living room is featured with a large flat-screen television mounted above a modern fireplace. A bay window offers views of greenery, complemented by a cozy seating area. Elegant decor includes a stylish mirror and a decorative table, enhancing the inviting ambiance.

4.87 out of 5 average rating, 30 reviews

SPA DEPARTURES NEAR THE SEA

Cottage in South Jamesport

A charming beach cottage is set against a clear blue sky, featuring a welcoming enclosed front porch. Surrounding gardens are filled with vibrant pink and purple flowers, framing the path leading to the front door and adding to the property’s tranquil ambiance.

5 out of 5 average rating, 9 reviews

Charming Beach Cottage, Vineyards & Sunset Views

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.

4.98 out of 5 average rating, 51 reviews

Chic cottage on lush, secluded acre by the beach.

A compact living area features a blue sofa adorned with patterned pillows and a geometric area rug. A dining table with two wooden chairs is positioned near a mirror reflecting natural light from the window. Potted plants add a touch of greenery to the space.

4.84 out of 5 average rating, 95 reviews

Cottage 3 minute walk Bridgehampton town

A vintage-style bicycle is positioned near a wooden deck, featuring a woven basket on the front. Soft pastel hues fill the sky in the background, creating a serene atmosphere. The bicycle is surrounded by natural greenery, adding to the outdoor charm of the setting.

4.71 out of 5 average rating, 7 reviews

Crowley Cottage

A spacious lawn is bordered by tall trees, providing a natural frame for the cottage. The vibrant green grass leads to a serene waterfront, where the lake reflects the sunlight. The peaceful setting invites relaxation and outdoor activities.

4.97 out of 5 average rating, 73 reviews

Head of Pond House - Waterfront Cottage

A modern living area is presented with a green sectional sofa adorned with patterned pillows. A wooden coffee table occupies the center, displaying a bouquet of hydrangeas, decorative bottles, and books. Natural light enhances the warm, inviting ambiance of the space.

4.94 out of 5 average rating, 32 reviews

Peaceful cottage, close to beaches

Private cottage rentals

A cozy living area features a light-toned sofa complemented by a stylish armchair. Skylights illuminate the space, highlighting the wood flooring and modern decor. A flat-screen TV is mounted on the wall, and a bookshelf adds a touch of character with various books.

4.91 out of 5 average rating, 153 reviews

East Hampton Fisherman’s Cottage with Secret Bath

Cottage in Shelter Island

A wooden dock extends over calm bay waters, leading towards a small boat anchored in the distance. Lush greenery lines the shoreline, and a clear blue sky complements the serene landscape. Birds are seen casually swimming near the water’s edge.

4.83 out of 5 average rating, 71 reviews

Large Waterfront Cottage on Historic Estate

4.78 out of 5 average rating, 50 reviews

A charming two-story cottage is surrounded by lush greenery and features a welcoming front porch with white railings. An American flag is displayed prominently, while the sloped roof is adorned with blue and white striped awnings. A well-maintained path leads from the sidewalk to the entrance.

Cottage in Rocky Point

Beautiful Boho Cottage by the beach

A light-filled living area features a white sofa with green accent pillows, complemented by a glass coffee table topped with stacked books. A guitar rests beside a side table, and large windows with woven shades provide a view of the outdoors. The space includes a dining area in the background.

4.98 out of 5 average rating, 106 reviews

Sag Harbor Cottage

The kitchen features modern white cabinetry and a wooden countertop, providing a spacious working area. Stainless steel appliances, including a microwave and coffee maker, are positioned neatly on the counter. A window allows natural light to illuminate the workspace.

4.89 out of 5 average rating, 114 reviews

Cozy Cottage Close to the Beach

A bright sleeping area is furnished with a queen bed, complemented by soft bedding and decorative pillows. Natural light fills the space through two small windows, with an antique mirror and a lamp providing additional lighting. A small seating area is visible to the side.

4.95 out of 5 average rating, 75 reviews

Beach Cottage 3 | New Suffolk | Northfork

5 out of 5 average rating, 10 reviews

Hamptons Waterfront Getaway – Stylish & Serene

A glass dining table is surrounded by four rattan chairs with light blue cushions. A simple striped runner is placed across the table, complemented by a vase of white flowers. Soft light illuminates the space, with a view of the adjoining living area and doorways visible in the background.