Cottage vacation rentals in East Hampton

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, 101 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.

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, 100 reviews

Calf Creek Cottage (Water Mill/Bridgehampton)

Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

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.

4.97 out of 5 average rating, 172 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!

An outdoor dining area is located beneath a wooden pergola, surrounded by a spacious lawn. A stone patio features a table with blue metal chairs. Lush greenery is visible in the background, along with a cottage painted in muted colors, accented by vibrant flowering bushes.

4.87 out of 5 average rating, 117 reviews

Secluded 1Br cottage on the lake, close to Ditch

This is the best of Montauk living, right by the lake, close to Ditch, and with an incredible, lush front yard suitable for outside dining or having a couple friends over for dinner. Walk down to the lake to enjoy the sunset, or stroll over to the Crow's Nest for drinks or dinner. No need to drive, it's well within walking distance. Join the many that have experienced the magic of our cottage at South Lake.

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, 357 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...

4.9 out of 5 average rating, 188 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!

Popular amenities for East Hampton cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Superhost

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!

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

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

4.95 out of 5 average rating, 100 reviews

Calf Creek Cottage (Water Mill/Bridgehampton)

Pet-friendly cottage rentals

Superhost

An open living space features a round dining table surrounded by four wooden chairs. A spacious couch is positioned nearby, complementing the light-colored walls and ceiling. Natural light enters through two windows adorned with sheer curtains, enhancing the clean and minimalistic decor.

4.6 out of 5 average rating, 47 reviews

Lovely Guesthouse in Southampton Village.

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, 13 reviews

Charming Beach Cottage, Vineyards & Sunset Views

Superhost

A cottage is nestled among a lush garden with blooming flowers and manicured grass. The exterior features a combination of green siding and gray shingles. Pathways made of stones lead to the entrance, embracing a serene and inviting environment.

4.76 out of 5 average rating, 25 reviews

Seabreeze #4: Charming Cottage Footsteps to Beach

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, 54 reviews

Chic cottage on lush, secluded acre by the beach.

A serene waterfront scene captures a vibrant sunset reflecting on calm waters. Silhouetted trees line the background, while a private dock extends into the water, featuring a railing. Warm hues of orange and pink fill the sky, creating a peaceful ambiance.

4.98 out of 5 average rating, 55 reviews

Stunning waterfront modern farmhouse with dock.

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

5 out of 5 average rating, 50 reviews

Steps to Beach•Baby & Beach Gear•Fire Pits•Bikes

Private cottage rentals

A cozy cape house is situated on a knoll, featuring a front porch with large windows. The gray shingle exterior complements the lush green lawn, which is bordered by tall grass. Trees and shrubbery frame the property, enhancing the natural surroundings.

5 out of 5 average rating, 30 reviews

Traditional Cape on Gardiner's Bay at Fresh Pond

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, 154 reviews

East Hampton Fisherman’s Cottage with Secret Bath

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

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 exterior of a charming blue home features a vibrant yellow front door and a symmetrical design. Lush greenery surrounds the property, with well-maintained gardens framing the entrance. A pathway leads toward the door, and ample lawn space enhances the inviting approach.

4.96 out of 5 average rating, 69 reviews

1870's Schoolhouse Converted to Cozy Cottage

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

Cottage in Shelter Island

A charming cottage is framed by vibrant pink azaleas, enhancing the exterior's appeal. Lush green grass surrounds the home, and a clear blue sky provides a bright backdrop. Windows allow natural light to fill the interior, which features a welcoming porch area.

4.96 out of 5 average rating, 48 reviews

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

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.