Cottage holiday rentals in Jamesport

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.

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 charming cottage is framed by lush greenery and well-maintained landscaping. The light-colored exterior features large windows and a welcoming green door. A stone walkway leads to the entrance, while a gravel driveway curves around, enhancing the natural setting.

4.96 out of 5 average rating, 197 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

4.98 out of 5 average rating, 167 reviews

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.

Cottage in North Fork

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.

4.94 out of 5 average rating, 362 reviews

A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.

Cottage in Milford

Fall Sale! CozyCottage/WalktoBeach/Pet-friendly

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

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, 171 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, 258 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.

4.91 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).

4.97 out of 5 average rating, 109 reviews

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.

Cottage in North Fork

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, 187 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!