House vacation rentals in Cutchogue

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, 75 reviews

Waterfront Beach Cottage

Renovated New Suffolk Waterfront Beach Cottage steps from water/beach/restaurants & more w/ water views from practically every window in the heart of the most special neighborhood in the north fork. Perfect for families with twn over full bunks, pvt mstr, grill, outdr shower and new kitchen. Bonus room has comfy couches & sunset views. Dine al fresco with water views or stroll to restaurants, apple picking or famous New Suffolk beach. Minutes from everything your vacation could need, year round.

4.94 out of 5 average rating, 334 reviews

An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.

Home in Bridgehampton

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

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

Whether you are looking for lots of outdoor space for the kids to explore, bike, play at the beach or splash around in the pool OR you are looking to explore all of the 38 Vineyards along Long Islands, this house is perfect for you. Open kitchen, dining and living space which then opens up to the deck and pool. 4 bedrooms, sleeping 8 comfortably. Two of the bedrooms are connected with a thru-door. Gated swimming pool. Minutes from the local sandy beach. Rental Permit: HMT24-00101 14-Day minimum

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.

4.95 out of 5 average rating, 270 reviews

A bright living space is featured, furnished with two light-colored chairs and a dark coffee table. A flat-screen television is mounted on the wall. A doorway leads to a bedroom, while natural light filters in through the windows, illuminating the neutral decor.

Home in Greenport

Aqua Vista

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 rental is 2nd floor apartment (only). Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy. Located right in Greenport. Walking distance to all the restaurants, bars, shopping, coffee shops.

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, 57 reviews

Luxury by the Sea!!

Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. This home is beautifully designed with too many architectural details to list. Property is fully furnished 🛋 with no detail spared . Open floor plan, spacious great room with gas fire place and flat screen, gourmet eat 🍝 in kitchen with large island is a wonderful place to entertain 🥂. Brand new washer/dryer, butlers pantry and mud room. Where the country meets the sea 🌊

4.87 out of 5 average rating, 137 reviews

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.

Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset 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! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.

A modern living area is highlighted by a gray sofa centered on a low coffee table. Two armchairs are placed to one side, while a textured area rug complements the space. Wall art hangs above the sofa, and natural light enters through large windows.

4.96 out of 5 average rating, 166 reviews

Walk to Beautiful Beach in Heart of Wine Country

Enjoy bright, comfortable and modern home in the heart of North Fork wine and farm country located just a quick walk from a gorgeous Peconic Bay beach with tennis/pickleball courts, volleyball and playground right on the beach. You'll have easy and quick access to the best of the east end: beautiful beaches, boating, fishing, fine and casual dining, vineyards, wineries, breweries, farms and farm stands offering fresh local produce, antique and local shops.

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.

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!

Superhost

An open living space features light-colored flooring and white walls. A dining table with four chairs is visible alongside a television mounted on a wall. Large glass doors lead to an outdoor area, enhancing the airy feel of the room.

4.83 out of 5 average rating, 23 reviews

NoFo Getaway: Pool, Farm Views, Beach Sunsets

Our family friendly home is set on a spacious green parcel, abutting a farm and the ocean with a pool, outdoor shower, large deck, stone firepit, pool shed, children's custom built playground, lawn games and more. Central air is installed throughout. The home features 4 bedrooms, 3 full bathrooms, 1 half bathroom and an outdoor shower. FOR VIRTUAL TOUR OR VIDEO TOUR PLEASE EMAIL AND WE WILL PROVIDE

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, 116 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.

Popular amenities for Cutchogue house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 184 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

4.91 out of 5 average rating, 141 reviews

Home in Springs

Serene + private ~ 1 block to waterfront dining

4.91 out of 5 average rating, 202 reviews

Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

4.94 out of 5 average rating, 116 reviews

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.

Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

4.95 out of 5 average rating, 204 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

4.94 out of 5 average rating, 166 reviews

A well-maintained outdoor pool area is surrounded by a wooden deck and lush greenery. Lounge chairs are positioned along the pool, with a shaded area provided by a large tree. The clear blue water of the pool reflects the sunlight, inviting relaxation.

Home in Water Mill

Astounding Watermill 5 Bedroom home with Pool

Superhost

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.

Home in Sag Harbor

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

4.86 out of 5 average rating, 138 reviews

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.

Luxury Hamptons Home with Heated Saltwater Pool

4.98 out of 5 average rating, 173 reviews

Weekly house rentals

4.9 out of 5 average rating, 10 reviews

Water Front Ospreys Nest Beach Rights Permit #1310

4.96 out of 5 average rating, 47 reviews

Wine Country Home

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, 29 reviews

Beautiful 1930s 4 bed 3 bath! Walk to Beach

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

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

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, 89 reviews

Le Petit Cottage Southold NY

4.9 out of 5 average rating, 41 reviews

Coastal Cottage on the Water

A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.

4.88 out of 5 average rating, 24 reviews

Stylish Beach Getaway: pool & walking location

Private house rentals

A serene outdoor fire pit area is framed by vibrant autumn foliage. Four wooden chairs surround a circular stone base, with a stump positioned at the center. Lush greenery provides a natural border, enhancing the setting's peaceful ambiance.

5.0 out of 5 average rating, 79 reviews

Greenport walk to beach & vineyard! Brand new home

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.

4.97 out of 5 average rating, 59 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

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

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.

4.8 out of 5 average rating, 45 reviews

Stylish Getaway in Greenport

A softly lit path of stone pavers leads to a furnished patio area, where a dining table and chairs are set under a vibrant red umbrella. Trees provide shade, and gentle garden lights illuminate the surrounding grass, creating a welcoming evening ambiance.

4.98 out of 5 average rating, 43 reviews

Vineyard Views & Bike to the Beach

An open-concept living area features a modern kitchen with stainless steel appliances and a large island. Two checkered armchairs are positioned around a wooden coffee table, while a dining table awaits at the back, complemented by stylish chairs and natural light from the windows.

4.98 out of 5 average rating, 46 reviews

Beachside Paradise!!

A light-filled living room features a working fireplace surrounded by a sleek white mantel. Comfortable seating options include two white sofas, a brown leather chair, and several blue poufs. Natural décor elements and artwork complement the space, creating a tranquil atmosphere.

4.98 out of 5 average rating, 48 reviews

Sprawling Modern Home Minutes from Beach

A spacious balcony extends along the side of the house, offering unobstructed views of the shimmering water. Weathered wooden benches provide seating, while the gentle waves can be observed lapping against the shore in the distance.