Cottage holiday 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 inviting living area features a cozy seating arrangement with a light-colored sofa and accent chairs. A wood-burning fireplace is surrounded by a stone mantle, while natural light fills the space through large windows. A dining area, art pieces, and wooden beams complement the bright atmosphere.

4.95 out of 5 average rating, 101 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.

The kitchen features sleek grey cabinets paired with white countertops and a tiled backsplash. Open shelving displays decorative items and plants. A stainless steel dishwasher is included, along with modern appliances. A window allows natural light to brighten the 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.

4.97 out of 5 average rating, 174 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 manicured lawn extends towards Fort Pond, featuring several white Adirondack chairs and a comfortable seating area with blue cushions. The shared outdoor space is bordered by a white picket fence, with the sparkling water visible in the background under a clear sky.

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, 358 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).

4.88 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, 190 reviews

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!

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 East Hampton cottage rentals

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

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

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

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, 101 reviews

Calf Creek Cottage (Water Mill/Bridgehampton)

Pet-friendly cottage rentals

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

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 patio area features wooden seating and a small glass-top table, with stone pavers and a well-maintained lawn. Surrounding greenery, including blooming plants, adds to the natural setting, while a fenced yard provides a feeling of privacy in the outdoor space.

4.97 out of 5 average rating, 36 reviews

Greenport Village cottage in central location

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.

Superhost

A well-equipped kitchen features light wood paneling and open shelves displaying dishware and plants. A stainless-steel oven and microwave are visible, along with a sleek sink and a wooden countertop. Natural light flows in through a nearby window, enhancing the space's functionality.

4.89 out of 5 average rating, 72 reviews

Bay View Cottage- Short Walk to Private Beaches

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

5 out of 5 average rating, 50 reviews

3 Min Walk to Beach|Close to Town| Fam-Friendly

4.94 out of 5 average rating, 64 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 South End

Adorable Cottage

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

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

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

Superhost

An outdoor heated pool is surrounded by a spacious patio, featuring clear blue water under a bright sky. Poolside lounge chairs are present, along with a safety railing for easy access. Privacy fencing and lush greenery provide a serene backdrop.