Waterfront holiday rentals in Cutchogue

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

4.88 out of 5 average rating, 156 reviews

Waterfront Autumn Escape in Wine Country: 2BR

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on your private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

4.95 out of 5 average rating, 248 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

4.88 out of 5 average rating, 114 reviews

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond - Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action

4.87 out of 5 average rating, 109 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.

4.91 out of 5 average rating, 149 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

A serene waterfront view features a sailboat gliding across calm waters. Lush green grass borders the shoreline, reflecting the tranquility of the environment. The clear blue sky stretches overhead, enhancing the peaceful atmosphere of the setting.

5 out of 5 average rating, 138 reviews

Hamptons Waterfront- Great Location- On the bay

Amazing Beachfront vacation home located directly on a private sandy beach on Shinnecock Bay. Stunning waterfront views- sunrises/sunsets. Have a bbq and relax right on the back deck and watch the boats pass by or take a quick walk or shuttle boat to some of the Hamptons best restaurants. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids).

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.

4.99 out of 5 average rating, 146 reviews

A spacious living area is equipped with a dark sofa, decorative cushions, and a light rug, complemented by natural light from windows. A wooden dining table with chairs is positioned near a sideboard, inviting relaxation and gatherings.

Cottage in Miller Place

Cozy Country Cottage #2

Relax and get away from it all at this newly renovated cottage in historic Miller Place. Enjoy your private fenced in backyard with your own deck, picnic table and BBQ. You can walk across the street to the historic Miller Place Pond or walk 2 blocks to the famous McNulty's Ice Cream Parlor. Take your beach gear 2 miles to Cedar Beach or go 4.5 miles to Port Jefferson for the best food and entertainment. So many options for dinning and entertainment. You are at the foot of wine country!

5 out of 5 average rating, 104 reviews

A lush backyard features a children's playset alongside a hammock. Adirondack chairs are arranged around a fire-pit, framed by trees and greenery. A serene waterfront view is visible, with a dock extending into the calm waters, enhancing the natural landscape.

Villa in The Hamptons

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

A dining set featuring a large wooden table with eight matching chairs is positioned under a spacious umbrella, offering shade. Lush greenery and a serene waterfront view are visible nearby, providing a peaceful outdoor setting.

4.98 out of 5 average rating, 104 reviews

Breezy Waterfront Home With private Dock

This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

4.85 out of 5 average rating, 113 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

4.93 out of 5 average rating, 150 reviews

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

Home in North Fork

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Popular amenities for Cutchogue waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

A serene view of the harbor is captured, showcasing gentle waves and sailboats anchored in the water. Lush green grass and tall trees frame the scene, providing a tranquil backdrop to the picturesque waterfront. The expansive sky is clear, allowing ample sunlight to illuminate the landscape.

Apartment in Shelter Island Heights

5 out of 5 average rating, 7 reviews

CHIC WATER VIEW APT. ON SHELTER ISLAND

Apartment in The Hamptons

A serene waterfront view showcases a private deck adorned with lush greenery and vibrant flowers. A saltwater hot tub and lounge area invite relaxation, while the expansive water stretches into the distance. Comfortable seating arrangements enhance the tranquil outdoor environment.

4.94 out of 5 average rating, 80 reviews

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

Apartment in The Hamptons

A cozy living area features wood-paneled walls and a neutral sofa positioned near a lamp and a chair. Natural light floods through the windows, illuminating a patterned rug on the hardwood floor. A television is mounted on the wall opposite the entrance.

4.92 out of 5 average rating, 12 reviews

Sugarloaf Annex

Apartment in The Hamptons

A bright and airy bedroom features a spacious bed with neutral bedding and decorative pillows. A large window with a sloped ceiling allows natural light to fill the space. A minimalist bookshelf and a cozy reading area with a lamp provide a welcoming touch.

4.94 out of 5 average rating, 16 reviews

Bayside Boho Retreat

A sandy beach scene is captured, featuring beachgoers relaxing on colorful lounge chairs under clear skies. The ocean water glimmers in the sunlight, while distant boats can be seen on the horizon. A few umbrellas provide shade for those enjoying the beach.

Apartment in Milford

Cozy apartment steps from the beach in Milford, CT

5 out of 5 average rating, 3 reviews

Apartment in North Fork

Greenport Condo with Stunning Views & Beach Access

Private room in South End

A view from the balcony showcases lush greenery and flowering plants in vibrant colors. The scene includes a neatly maintained garden, with varying heights of trees lining the property, and a hint of a gravel path leading away into the surroundings.

4.99 out of 5 average rating, 145 reviews

Cozy guest room - quiet getaway - wine country

4.79 out of 5 average rating, 344 reviews

A spacious living area showcases a light grey sectional sofa and a matching loveseat arranged around a wooden coffee table. A striped area rug adds a pop of color to the dark flooring. Shelves line the walls, and large windows allow natural light to fill the room.

Apartment in North Fork

Amazing Greenport Village Apartment in CENTER!

Waterfront house rentals

4.93 out of 5 average rating, 136 reviews

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

Joyful Beach House, viewing The Great South Bay

4.8 out of 5 average rating, 358 reviews

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

The Hilltop Harborview

A comfortable living area features two light-colored sofas with decorative pillows, arranged around a central glass coffee table. A flat-screen TV is mounted on the wall, and large sliding doors provide scenic views of the outdoor greenery and natural surroundings.

4.95 out of 5 average rating, 234 reviews

Ritz-East Hampton Cottage- 5 stars

A wooden deck features comfortable seating with white cushions, positioned around a small table set with tea and pastries. Lush green grass surrounds the area, dotted with tall trees, while a clear view of the harbor can be seen in the background.

4.82 out of 5 average rating, 38 reviews

Historic East Hampton Home - Private Beach Access

4.89 out of 5 average rating, 28 reviews

A beachfront house with a wooden exterior is depicted, featuring multiple windows adorned with green planters. Soft sand covers the area in front, leading to the water, which reflects the clear blue sky. A small chair is visible on the sand, emphasizing the serene beach setting.

Home in North Fork

The Sandy Shack - Coastal Escape

5 out of 5 average rating, 108 reviews

A view of Long Island Sound at sunset is captured from the balcony. Gentle waves reflect the colors of the sky, ranging from soft pink to deep orange, while Charles Island is visible in the distance, framed by the serene horizon.

Home in Milford

Milford Beach House - Newer Construction!

4.83 out of 5 average rating, 29 reviews

The image presents a coastal view featuring a well-maintained property adjacent to the shoreline. The sky displays a gradient of colors at sunset, and gentle waves can be seen lapping against the rocky beach. Surrounding greenery complements the tranquil setting.

Home in North Fork

North Fork Sound Front Home with Pool

A renovated kitchen is presented, featuring a central island with bar stools and modern appliances. Soft green backsplash tiles add a refreshing touch, while natural light pours in through the windows, illuminating the clean lines and open layout of the space.

4.94 out of 5 average rating, 31 reviews

Hamptons Home, 3bed/2bath Near Beach & Restaurants

Waterfront condo accommodation

The living area features a comfortable seating arrangement with a dark couch and light-colored accent chairs. A dining table sits nearby, accompanied by additional seating. Large windows offer natural light, with greenery visible outside. A flat-screen TV and decorative mirror add to the space.

4.83 out of 5 average rating, 6 reviews

Beautiful 2 Bedroom 2 Bathroom Pool-Side Condo

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

4.85 out of 5 average rating, 157 reviews

2 BR Waterfront Autumn Escape in Wine Country

The living area showcases a comfortable sofa adorned with decorative cushions, complemented by a coffee table. A kitchen area with modern appliances is visible, alongside a dining cart. Art pieces frame the walls, and natural light enters through sliding glass doors.

4.88 out of 5 average rating, 103 reviews

Waterfront Condo C-204 at The Cliffside Resort

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.