Cottage holiday rentals in Southampton

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 serene beach view captures gentle waves lapping at the shore under a soft light. The smooth sand stretches into the distance, with subtle textures and footprints creating a sense of tranquility. A distant silhouette of a bird can be seen against the sky.

4.91 out of 5 average rating, 649 reviews

Montauk Oceanview

Wake up to ocean vistas every morning in a charming cottage. There are stunning views of the waves, soothing ocean sounds, and a gentle sea breeze. Sip coffee on a sun-drenched porch, enjoy a sunset stroll along sandy beaches, or simply unwind with the mesmerizing horizon as your backdrop, this cottage provides the perfect blend of comfort and charm. The cottage features a cozy interior with a working fireplace, modern amenities, and large windows that showcase the stunning seaside scenery.

Cottage in Port Jefferson Station

A charming cottage with a red exterior is surrounded by a lush garden filled with various plants and flowers. A spacious covered porch extends across the front, offering a welcoming entryway. The well-manicured lawn is complemented by vibrant greenery and colorful blooms, creating a pleasant outdoor space.

4.8 out of 5 average rating, 523 reviews

The Red Cottage Circa 1936

This cottage is a gem to be found! From the primary room to the charming loft, this cottage can sleep 6! There is a full working kitchen. For those who wish to do exploring, you will be centrally located on LI giving you great ease in using LI rail road (.5 mile) from cottage and Port Jeff Ferry (1mile)from cottage. There is a large fenced in yard with BBQ and outdoor seating if you wish to dine in. Dogs are allowed w/prior notice and a $65 pet fee. You won’t beat this value! Has it All!!

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, 168 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.

4.97 out of 5 average rating, 179 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!

4.95 out of 5 average rating, 265 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.

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.

4.92 out of 5 average rating, 142 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.

4.98 out of 5 average rating, 363 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).

The open kitchen and dining area feature warm wooden flooring and cabinetry. A central island with bar stools provides seating, while a dining table is positioned by large windows, allowing natural light to brighten the space. Appliances are neatly arranged, enhancing functionality.

4.88 out of 5 average rating, 111 reviews

Apples and pumpkins and Beaches!

This cottage has high ceilings, is bright and airy, has a wrap around deck with a great overhang for hanging out in the shade or sun. You can not see a neighbor. It has been described as “an adult tree house.” Just a fun and relaxing place to be. It is on over an acre of rustic property. Perfect for watching wildlife.

Cottage in Shelter Island

A traditional New England-style house features a front porch supported by white columns. Two white chairs and a small table are arranged on the porch, complemented by a dark front door. Large windows allow natural light to fill the space, surrounded by green landscaped areas.

4.97 out of 5 average rating, 116 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

A single-story house is set against a backdrop of green grass and towering trees. Natural light illuminates the exterior, which features light-colored siding and a welcoming front porch. The spacious yard provides ample outdoor space for relaxation.

4.97 out of 5 average rating, 110 reviews

Riverhead Farmhouse

In the center of it all lies this newly renovated farm ranch, located in a farming area of Riverhead town. It has a private and tranquil setting but yet so close to so many things like shopping, wineries, breweries, farm stands, restaurants and the bay and ocean.

4.9 out of 5 average rating, 191 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 Southold

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!

Popular amenities for cottage rentals in Southampton

Kitchen

Wifi

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

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 bright room is shown with a spacious bed featuring striped linens. Sheer curtains frame a sliding glass door that opens to a landscaped garden. A glimpse of outdoor seating is visible through the doorway, surrounded by greenery.

4.83 out of 5 average rating, 109 reviews

Private Room in the House that Art Built

4.13 out of 5 average rating, 8 reviews

The House that Art Built in the Hamptons

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

Pet-friendly cottage rentals

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.

4.93 out of 5 average rating, 14 reviews

Charming Beach Cottage, Vineyards & Sunset Views

A spacious great room is highlighted by a cathedral ceiling with exposed wooden beams. Comfortable sofas frame a central coffee table, while large windows provide natural light, accentuated by sheer white curtains. A cozy reading nook is positioned against the wall, complemented by a variety of books.

5 out of 5 average rating, 25 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

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, 97 reviews

Cottage 3 minute walk Bridgehampton town

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

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, 74 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

4.94 out of 5 average rating, 67 reviews

A seating area is arranged with five Adirondack chairs surrounding a wooden table, nestled on a green lawn. A large tree provides shade to the space. In the background, a cottage with a yellow exterior and blue roof is visible, complemented by a patio area.

Cottage in Southold

Adorable Cottage

The kitchen features modern gray cabinetry and stainless steel appliances. A wooden dining table is accompanied by three black stools. Natural light fills the space through the window, and a small plant is placed on the countertop, adding a touch of greenery.

4.8 out of 5 average rating, 35 reviews

Beach cottage 9.6 Miles from 2026 US Golf Open

Private cottage rentals

A welcoming living room features a light-colored sectional sofa with navy accent pillows, situated near a rustic brick fireplace. Two windows allow natural light to fill the space, with wooden paneling and a natural fiber rug providing warmth. A small coffee table completes the seating arrangement.

4.96 out of 5 average rating, 53 reviews

Apres Sea : Renovated cottage close to all

Cottage in Shelter Island

Two wooden chairs are positioned on a grassy area overlooking the calm water. A fire pit sits in between the chairs, and a swing hangs from a nearby tree. In the background, a dock extends into the water, framed by trees.

4.97 out of 5 average rating, 113 reviews

Shelter Island Waterfront Getaway

4.8 out of 5 average rating, 54 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

4.96 out of 5 average rating, 69 reviews

1870's Schoolhouse Converted to Cozy Cottage

Cottage in Port Jefferson Station

An inviting exterior of the Cherry Blossom Cottage is depicted, featuring a basketball hoop secured next to a stone pathway that leads to the house. The area is surrounded by trees, with a landscaped garden showcasing flowers and sitting areas for outdoor relaxation.

5 out of 5 average rating, 32 reviews

A Hidden Gem! Cozy Cottage with huge Pool & Garden

A serene coastal view captures a vibrant sunset, where the sun dips below the horizon, casting warm hues across the sky. Gentle waves lap against dark rocks, creating a tranquil atmosphere along the shore. The scene evokes a sense of calm and natural beauty.

4.92 out of 5 average rating, 63 reviews

Cottage in Calverton

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.