House holiday rentals in Cutchogue

4.91 out of 5 average rating, 140 reviews

Chic w/ large pool ~ 1 block to waterfront dining

Serene, chic Hamptons oasis! Located 1 block from waterfront dining + 8 mins to beaches + Main St. Enjoy your large private home nestled in nature, perched back on a quiet tree lined street. Swim in your pool, spark up the BBQ + firepit under the starry sky! Cook in your Chef's kitchen + stream on the 80' TV. Walk 1 block to waterfront dinner + cocktails watching the best sunsets. Enjoy morning coffee on the sea. Walk back home in 4 minutes. You'll be 8 minutes to Main St., beaches + more!

FamilyLocationAmenities

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, 263 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.

ValueFamilyHeating

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

4.95 out of 5 average rating, 519 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

FamilyValueAir conditioning

4.85 out of 5 average rating, 158 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!

ValueLocationAmenities

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

4.93 out of 5 average rating, 134 reviews

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

LocationFamilyBathroom

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

4.97 out of 5 average rating, 218 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

ValueLocationGetting around

4.97 out of 5 average rating, 295 reviews

The front exterior of the bungalow is showcased, featuring a wooden fence that provides privacy and a garden filled with hydrangeas. The house displays large windows that invite natural light, set against a backdrop of gravel and greenery.

Home in Greenport

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

FamilyValueBiking

4.95 out of 5 average rating, 203 reviews

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.

Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

LocationFamilyAccess

4.95 out of 5 average rating, 394 reviews

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

Home in Greenport

The Sandpiper

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

FamilyValuePets

4.95 out of 5 average rating, 321 reviews

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

Home in Sag Harbor

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

ValueLocationLong stay

A modern cottage is set amidst lush greenery, featuring a spacious rear deck and a lower patio area with two lounge chairs. The second story includes a covered deck with an awning, while large windows invite natural light into the interior.

4.92 out of 5 average rating, 115 reviews

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

FamilyLocationCheckout

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

4.96 out of 5 average rating, 213 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

FamilyValueView

Popular amenities for Cutchogue house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.87 out of 5 average rating, 137 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

LocationFamilyView

A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.

4.94 out of 5 average rating, 116 reviews

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

LocationFamilyAccuracy

Home in Westhampton Beach

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

4.98 out of 5 average rating, 172 reviews

Luxury Hamptons Home with Heated Saltwater Pool

LocationFamilyGetting around

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

4.97 out of 5 average rating, 152 reviews

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

LocationFamilyComfort

Superhost

A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.

4.89 out of 5 average rating, 117 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

ValueLocationWi-Fi

An aerial view captures a backyard featuring a heated pool surrounded by comfortable seating and a dining area. A deck is adorned with lounge chairs and a patterned rug, while manicured grass enhances the outdoor space. Sunlight reflects off the crystal-clear pool water.

4.87 out of 5 average rating, 107 reviews

Hampton Bays village summer home!

LocationValueCleanliness

4.78 out of 5 average rating, 143 reviews

The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.

Home in East Hampton

Sprawling Hamptons Estate with Hot Tub & Amenities

ValueFamilyCheckout

A spacious living area is illuminated by natural light from skylights and large windows. A soft sofa is positioned on a light-colored rug, accompanied by a round pouf. Dining space is visible in the background, showcasing a simple wooden table and chairs.

4.95 out of 5 average rating, 87 reviews

Nassau Point, North Fork Home w/ Pool

LocationFamilyCondition

Weekly house rentals

5.0 out of 5 average rating, 45 reviews

Wine Country Home

FamilyValueParking

A spacious backyard is featured, with a circular stone fire pit surrounded by several colorful Adirondack chairs. Lush green grass extends towards a charming white house in the background, bordered by trees under a clear blue sky.

5.0 out of 5 average rating, 45 reviews

Private Waterfront Access + Hot Tub + Scenic Yard

FamilyValueLayout

A spacious gourmet kitchen is equipped with white cabinetry and a large island featuring a light-colored countertop. Pendant lights hang above the island, and stainless steel appliances are visible in the background, complemented by a tile backsplash and modern fixtures throughout.

4.95 out of 5 average rating, 56 reviews

Luxury by the Sea!!

ValueLocationLayout

The exterior of a renovated cottage is displayed, featuring light green siding and white trim. Large windows invite natural light, while a welcoming front porch is framed by greenery. A gravel pathway and well-maintained landscaping enhance the peaceful setting.

5.0 out of 5 average rating, 26 reviews

Beautiful 1930s 4 bed 3 bath! Walk to Beach

FamilyLocationParks

The exterior of the cottage is highlighted by a well-maintained yard featuring a lush green lawn. A patio area with seating is visible, surrounded by flowering shrubs and trees. Multiple large windows offer a view into the inviting living spaces within.

4.95 out of 5 average rating, 74 reviews

Waterfront Beach Cottage

LocationValueParks

A comfortable bedroom features a queen-sized bed with a patterned quilt and decorative pillows. A sofa is positioned nearby, with a small side table beside it. Natural light filters in through a window adorned with light curtains, enhancing the inviting space.

4.96 out of 5 average rating, 25 reviews

Sunny Harbor Suite

LocationValueBeach

4.9 out of 5 average rating, 41 reviews

Coastal Cottage on the Water

LocationFamilyDecor

A living area features a comfortable blue couch paired with two round wooden coffee tables. Natural light enters through large windows, illuminating the space. A modern lamp and a decorative shelf add to the décor, while a minimalist fireplace is visible, enhancing the cozy atmosphere.

4.89 out of 5 average rating, 88 reviews

Le Petit Cottage, Southold, NY

ValueLocationAccuracy

Private house rentals

The exterior of a charming house is featured, showcasing warm orange siding with blue accents. A spacious deck with wooden railing and a grill is visible, surrounded by lush greenery. Large windows allow natural light into the interior, creating a welcoming atmosphere.

4.97 out of 5 average rating, 78 reviews

Mattituck Dream House - Rental Opportunity

ValueLocationHiking

A charming blue house is framed by lush green trees, with a welcoming front porch. Large windows invite natural light, while a white picket fence complements the tranquil outdoor setting. The spacious yard features vibrant grass, enhancing the peaceful atmosphere.

4.96 out of 5 average rating, 57 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

FamilyLocationIndoor spaces

A single-story house is depicted with a white exterior, featuring a light blue door and several windows. A pathway of stone slabs leads to the entrance, surrounded by neatly landscaped greenery and shrubs. Trees in the background show vibrant autumn foliage.

4.98 out of 5 average rating, 45 reviews

Brand New Charming Beach House

LocationFamilyIndoor spaces

Superhost

A well-lit living area features a large window and a glass door leading to the outdoor space. A modern fireplace is centered in the room, complemented by stylish furniture, including a curved sofa and a standing lamp. Art decor adds visual interest to the wall.

4.81 out of 5 average rating, 42 reviews

Stylish Getaway in Greenport

ValueFamilyDecor

5.0 out of 5 average rating, 32 reviews

A modern two-story home features white siding and multiple windows that allow ample natural light. The entryway is framed by a small covered porch with a railing. A manicured lawn with stone pathways leads to the entrance, surrounded by low-lying shrubs.

Home in Greenport

Pennington House

LocationFamilyNearby

The living area features a soft-colored sofa resting against a light gray wall. A coffee table sits atop a striped rug, while a decorative chandelier hangs above. Two accent chairs flank the table, and a flat-screen TV is placed in a nearby console under a bright window.

4.92 out of 5 average rating, 24 reviews

East end home away from home

FamilyLocationGetting around

A light-filled living area features two white sofas, accented with pillows and a throw blanket. A large window offers views of the surrounding greenery, while a dining area is visible through the nearby glass door. A modern chandelier complements the space.

5.0 out of 5 average rating, 28 reviews

Modern Mattituck Escape in Prime North Fork

FamilyValueAmenities

A seasonal pool is framed by leafy trees, with a stone patio featuring lounge chairs for relaxation. Surrounding gardens are visible, enhancing the tranquil atmosphere of the space.